Hi, we're Oscar. We're hiring an Applied AI Engineer to join our AI team.

Oscar is the first health insurance company built around a full stack technology platform and a focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role

Join Oscar’s AI team to build and launch transformative AI-powered products that redefine the healthcare experience for millions. As an Applied AI Engineer, you’ll take end-to-end ownership of high-impact projects—conceiving, prototyping, and deploying generative AI solutions that solve real-world problems across the healthcare ecosystem.You’ll work alongside a world-class team of engineers and data scientists, rapidly iterating on ideas and shipping production-ready applications that drive measurable business and user outcomes. You’ll have the autonomy to identify opportunities, experiment with the latest AI models and techniques, and deliver solutions that streamline operations, improve patient experiences, and move the needle for Oscar and our members.

You will report to the Sr. Director, AI.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $180,504 - $236,911 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities

• Lead the design, development, and deployment of AI-driven products and features, from zero-to-one prototypes to robust production systems.
• Collaborate cross-functionally with product, design, and business teams to deeply understand user needs and deliver solutions that move key metrics.
• Rapidly experiment with new models, techniques, and tools (including LLMs, RAG, and agentic workflows), iterating based on data and user feedback.
• Build and scale full-stack applications and intelligent agents that automate complex healthcare workflows and deliver seamless user experiences.
• Stay on the cutting edge of the AI ecosystem, evaluating and integrating emerging technologies to keep Oscar at the forefront of healthcare innovation.
• Contribute to Oscar’s AI strategy and technical vision, helping shape the future of healthcare through technology.
• Other duties as assigned

Qualifications

• 7+ years of professional experience in software engineering, data science, or a related field, with a track record of impactful accomplishments
• Strong Python programming skills
• Experience solving complex, ambiguous problems 
• Experience designing and analyzing experiments or evaluations
• Experience or an interest in prototyping full-stack applications

Bonus Points

• Experience with the healthcare industry. Familiarity with claims or clinical data.
• Degree in math, statistics, data science, or engineering.
• Our ideal candidate is a data scientist with an engineering background, an engineer with a data science background, or a founder-type who combines product thinking, rapid prototyping, and hands-on coding to deliver real-world impact.
• Experience with NLP, neural networks, transformers, and modern AI frameworks.
• Knowledge of containerization and deployment tools (e.g., Docker, Kubernetes) or full-stack development (e.g., React, Golang).
• Experimental mindset: comfort with testing hypotheses and iterating on failures.

Hi, we're Oscar. We're hiring a Senior Data Scientist to join our Data Team. 

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

We are a Data Science team at Oscar dedicated to improving the Member Experience by embedding advanced analytics into our core technology and operations. We focus on building data products that bridge the gap between complex health insurance workflows and seamless, member-centric service.

You will drive the evolution of our member-facing tools by developing the LLM frameworks and ML models that underpin our automated support systems and digital interfaces. You will be responsible for evaluating both tool performance and member behavior to surface deep insights that inform our broader product and operations strategy.

You will report into the Lead Data Scientist.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $163,944 - $215,176.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Works with team and manager to impact longer term strategies and roadmap
• Sets shorter term roadmap for team
• May manage data scientists and/or analysts
• Interacts and collaborates closely with data and business counterparts across functional areas
• Researches, develops, and maintains data pipelines, statistical/ML models, and/or advanced analyses
• Compliance with all applicable laws and regulations
• Other duties as assigned 

Requirements:

• 4+ years of industry or other quantitative technical fields (which may include academia).
• 3+ years of work experience working with SQL, R, and/or Python to query, manipulate and analyze data
• 3+ years experience building data models, using more advanced analytics methods, statistical modeling, and/or data processing

Bonus points:

• Advanced degree in a quantitative or technical field
• Experience in the healthcare, finance and/or insurance industries
• Experience evaluating consumer-facing digital products in collaboration with Product and Engineering teams

Hi, we're Oscar. We're hiring an Analytics Engineer I to join our Data Team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Analytics Engineer I designs, builds, and maintains dimensional models and data transformations that convert raw operational data into reliable, well-structured analytical assets. You’ll work within Oscar’s unified data foundation in dbt, partnering with domain experts and stakeholders to capture business logic and translate it into dimensional models that serve analytics use cases across the organization. Under the guidance of more senior Analytics Engineers, you’ll build and maintain models, implement automated tests to ensure long-term data product health, and contribute to the semantic layer that powers enterprise business intelligence. This is a hands-on role focused on growing your craft in dimensional modeling, SQL, and analytics engineering within a healthcare environment.

You will report into the Associate Director, Data Science. 

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule.

Pay Transparency: The base pay for this role is: $106,812 - $140,190.75 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities:

• Demonstrates a strong working knowledge of Oscar's analytics technologies and tools as well as the breadth of content contained within.
• Contribute to the development and documentation of best practices for engineering and analytics development, consistent with industry standards and internal guidelines.
• Under the guidance of more senior Analytics Engineers, partner with Subject Matter Experts and Business stakeholders to explore data, define business requirements, design and implement solutions for one or more data transformation and/or downstream semantic layer systems.
• Advance the Analytics Engineering roadmap by executing on small-to-medium projects with minimal oversight
• Contribute to the administration of the analytics platform, including but not limited to active participation in support channels and actioning  access requests.
• Leverage a working knowledge of existing data quality checks as well as monitoring and alerting pipelines to perform Root Cause Analyses of data defects as needed and escalate to the appropriate team when warranted.

Requirements:

• 1+ years of experience in Analytics Engineering, Data Science, or a related field.
• 1+ years of experience working with SQL.
• 1+ years of experience developing in a semantic modeling language (e.g. LookML).
• 1+ years of experience developing within a modern data transformation tool like DBT.
• 1+ years of experience with cloud database tools (GCP, AWS, Azure).

Bonus points:

• Experience working with healthcare or insurance industry data, analytics, and reporting.
• Experience with Google Cloud Platform and dbt.
• Experience building dimensional models (star schemas, slowly changing dimensions).
• Strong communication skills, as demonstrated by experience partnering with non-technical stakeholders.

Hi, we're Oscar. We're hiring a to join our Clinical Data Analytics team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

You will partner closely across the organization to identify and manage inefficiencies proactively in the business. You will support business units in scoping, analyzing and monitoring performance of key financial and utilization metrics in service of company goals. You will independently drives the scoping & execution of analytical requests, including working with stakeholders to define key questions, scope methodologies and results. You will be called upon to speak to prepared analysis both internally and externally.

You will report into the Senior Manager, Clinical Analytics.

Work Location: This position is based in our Tempe, Arizona office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $91,659 - $120,303 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Responsible for owning insights generation and follow-up for a major business unit, serving as the first point of contract for Sr. Managers and Associate Directors
• Analyze data to support business teams in making better informed, data-driven decisions
• Use data to tell a story that non-technical colleagues will be able to understand, including packaging and presenting findings in a clear, concise and compelling manner
• Recognize the need to enhance essential operational and analytical dashboards, and define the requirements to enhance them as our user's needs evolve
• Identify opportunities to create models and tools that produce relevant insights to identify healthcare inefficiencies and generate insights to remove inefficiencies
• Collaborate across the organization, including owning stakeholder relationships with managers & senior managers , to identify actions to achieve improvements and monitor initiative impact
• Support other strategic projects as assigned to meet business needs
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 3+ years of technical work experience using analytical tools and writing analytical reports
• 3+ years demonstrated ability to work with large datasets and distill analyses into relevant insights with a structured and systematic thought process
• Strong communication skills, verbal and written, around business reporting impact and requirements, as demonstrated by 5+ examples / projects of presenting analysis to Leadership (Director+)
• 3+ years experience in SQL, with the ability to filter, aggregate, and build CTEs, or proficiency in R or Python, including experience with Pandas, for loops, and statistical tests
• 3+ years experience developing dashboards and working with Looker, or other business intelligence/data visualization tools
• 3+ years experience, including proficiency in Google Sheets or Excel skills, with ability to use VLookup, nested if statements and connected Sheets
• 1+ years experience in healthcare, consulting, finance or the insurance industry

Bonus points:

• 2+ years experience in preparing healthcare analytics and reporting
• 2+ years experience managing value-based contracts at a payer or a provider organization (ACO, CIN, MSO etc.)
• Exposure to healthcare contract negotiations, risk adjustment, ACA marketplace, quality of care, and/or population health experience

Hi, we're Oscar. We're hiring a to join our Clinical Data Analytics team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

You will partner closely across the organization to identify and manage inefficiencies proactively in the business. You will support business units in scoping, analyzing and monitoring performance of key financial and utilization metrics in service of company goals. You will independently drives the scoping & execution of analytical requests, including working with stakeholders to define key questions, scope methodologies and results. You will be called upon to speak to prepared analysis both internally and externally.

You will report into the Senior Manager, Clinical Analytics.

Work Location: This is a remote position, open to candidates who reside in: Dallas, Texas. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $91,659 - $120,303 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Responsible for owning insights generation and follow-up for a major business unit, serving as the first point of contract for Sr. Managers and Associate Directors
• Analyze data to support business teams in making better informed, data-driven decisions
• Use data to tell a story that non-technical colleagues will be able to understand, including packaging and presenting findings in a clear, concise and compelling manner
• Recognize the need to enhance essential operational and analytical dashboards, and define the requirements to enhance them as our user's needs evolve
• Identify opportunities to create models and tools that produce relevant insights to identify healthcare inefficiencies and generate insights to remove inefficiencies
• Collaborate across the organization, including owning stakeholder relationships with managers & senior managers , to identify actions to achieve improvements and monitor initiative impact
• Support other strategic projects as assigned to meet business needs
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 3+ years of technical work experience using analytical tools and writing analytical reports
• 3+ years demonstrated ability to work with large datasets and distill analyses into relevant insights with a structured and systematic thought process
• Strong communication skills, verbal and written, around business reporting impact and requirements, as demonstrated by 5+ examples / projects of presenting analysis to Leadership (Director+)
• 3+ years experience in SQL, with the ability to filter, aggregate, and build CTEs, or proficiency in R or Python, including experience with Pandas, for loops, and statistical tests
• 3+ years experience developing dashboards and working with Looker, or other business intelligence/data visualization tools
• 3+ years experience, including proficiency in Google Sheets or Excel skills, with ability to use VLookup, nested if statements and connected Sheets
• 1+ years experience in healthcare, consulting, finance or the insurance industry

Bonus points:

• 2+ years experience in preparing healthcare analytics and reporting
• 2+ years experience managing value-based contracts at a payer or a provider organization (ACO, CIN, MSO etc.)
• Exposure to healthcare contract negotiations, risk adjustment, ACA marketplace, quality of care, and/or population health experience

Hi, we're Oscar. We're hiring a to join our Clinical Data Analytics team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

You will partner closely across the organization to identify and manage inefficiencies proactively in the business. You will support business units in scoping, analyzing and monitoring performance of key financial and utilization metrics in service of company goals. You will independently drives the scoping & execution of analytical requests, including working with stakeholders to define key questions, scope methodologies and results. You will be called upon to speak to prepared analysis both internally and externally.

You will report into the Senior Manager, Clinical Analytics.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $101,844 - $133,670 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Responsible for owning insights generation and follow-up for a major business unit, serving as the first point of contract for Sr. Managers and Associate Directors
• Analyze data to support business teams in making better informed, data-driven decisions
• Use data to tell a story that non-technical colleagues will be able to understand, including packaging and presenting findings in a clear, concise and compelling manner
• Recognize the need to enhance essential operational and analytical dashboards, and define the requirements to enhance them as our user's needs evolve
• Identify opportunities to create models and tools that produce relevant insights to identify healthcare inefficiencies and generate insights to remove inefficiencies
• Collaborate across the organization, including owning stakeholder relationships with managers & senior managers , to identify actions to achieve improvements and monitor initiative impact
• Support other strategic projects as assigned to meet business needs
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 3+ years of technical work experience using analytical tools and writing analytical reports
• 3+ years demonstrated ability to work with large datasets and distill analyses into relevant insights with a structured and systematic thought process
• Strong communication skills, verbal and written, around business reporting impact and requirements, as demonstrated by 5+ examples / projects of presenting analysis to Leadership (Director+)
• 3+ years experience in SQL, with the ability to filter, aggregate, and build CTEs, or proficiency in R or Python, including experience with Pandas, for loops, and statistical tests
• 3+ years experience developing dashboards and working with Looker, or other business intelligence/data visualization tools
• 3+ years experience, including proficiency in Google Sheets or Excel skills, with ability to use VLookup, nested if statements and connected Sheets
• 1+ years experience in healthcare, consulting, finance or the insurance industry

Bonus points:

• 2+ years experience in preparing healthcare analytics and reporting
• 2+ years experience managing value-based contracts at a payer or a provider organization (ACO, CIN, MSO etc.)
• Exposure to healthcare contract negotiations, risk adjustment, ACA marketplace, quality of care, and/or population health experience

Hi, we're Oscar. We're hiring a to join our Clinical Data Analytics team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

You will partner closely across the organization to identify and manage inefficiencies proactively in the business. You will support business units in scoping, analyzing and monitoring performance of key financial and utilization metrics in service of company goals. You will independently drives the scoping & execution of analytical requests, including working with stakeholders to define key questions, scope methodologies and results. You will be called upon to speak to prepared analysis both internally and externally.

You will report into the Senior Manager, Clinical Analytics.

Work Location: This is a remote position, open to candidates who reside in: Atlanta, Georgia. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $91,659 - $120,303 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Responsible for owning insights generation and follow-up for a major business unit, serving as the first point of contract for Sr. Managers and Associate Directors
• Analyze data to support business teams in making better informed, data-driven decisions
• Use data to tell a story that non-technical colleagues will be able to understand, including packaging and presenting findings in a clear, concise and compelling manner
• Recognize the need to enhance essential operational and analytical dashboards, and define the requirements to enhance them as our user's needs evolve
• Identify opportunities to create models and tools that produce relevant insights to identify healthcare inefficiencies and generate insights to remove inefficiencies
• Collaborate across the organization, including owning stakeholder relationships with managers & senior managers , to identify actions to achieve improvements and monitor initiative impact
• Support other strategic projects as assigned to meet business needs
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 3+ years of technical work experience using analytical tools and writing analytical reports
• 3+ years demonstrated ability to work with large datasets and distill analyses into relevant insights with a structured and systematic thought process
• Strong communication skills, verbal and written, around business reporting impact and requirements, as demonstrated by 5+ examples / projects of presenting analysis to Leadership (Director+)
• 3+ years experience in SQL, with the ability to filter, aggregate, and build CTEs, or proficiency in R or Python, including experience with Pandas, for loops, and statistical tests
• 3+ years experience developing dashboards and working with Looker, or other business intelligence/data visualization tools
• 3+ years experience, including proficiency in Google Sheets or Excel skills, with ability to use VLookup, nested if statements and connected Sheets
• 1+ years experience in healthcare, consulting, finance or the insurance industry

Bonus points:

• 2+ years experience in preparing healthcare analytics and reporting
• 2+ years experience managing value-based contracts at a payer or a provider organization (ACO, CIN, MSO etc.)
• Exposure to healthcare contract negotiations, risk adjustment, ACA marketplace, quality of care, and/or population health experience

Pay Transparency:

The base pay for this role is: $163,944 - $215,176 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities

• Manage a team of engineers, focusing on professional development, performance management, and technical mentorship.
• Oversee the planning, execution, and delivery of complex technical projects, ensuring they meet deadlines and quality standards.
• Lead architectural decisions and technical design for full-stack applications.
• Partner with Product, Design, and other engineering leads to define roadmaps and solve business challenges.
• Promote best practices in software development, including code reviews, testing, and documentation.
• Identify and resolve bottlenecks in the development process to improve team velocity and system reliability.

Qualifications

• 6+ years of professional software engineering experience, working with a variety of technologies, and have increasingly impactful accomplishments.
• 2+ years of experience in engineering management or a technical lead role.
• Experience proposing, experimenting, and iterating, whether it be a new shiny technology or an arcane, ill-conceived data structure.
• Experience with technical contributions, improving the quality of what you create, and are excited to build fault-tolerant, and scalable software systems.
• Demonstrates solid understanding of the practical application of CS concepts within their team.
• Consistently writes stable, correct, and maintainable code with little oversight; writes modular, adaptable code with guidance.

Bonus Points

• Advanced experience with frontend architecture and building end-to-end web applications.
• Proficiency in designing micro services, optimizing database performance, or working with distributed systems.
• Familiarity with integrating Machine Learning models, working with Large Language Models (LLMs), or building data-driven features.
• Background in healthcare or other highly regulated industries.

Hi, we're Oscar. We're hiring a Senior Product Manager, Authorization Services to join our Product team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Oscar is looking for a Senior Product Manager to help transform how healthcare authorizations work—one of the most complex, costly, and frustrating parts of the payer ecosystem. Today, prior authorization creates friction across the system: members face delays in care, providers navigate administrative burden, and payers incur significant operational cost. Our mission is to fundamentally redesign this experience.

You will be part of the Authorization Services team, which is rethinking utilization management from a reactive approval process into a proactive, intelligent system that guides members to the right care—while minimizing or eliminating the need for manual authorization altogether.

This is a high-impact, high-visibility role at the center of Oscar’s next phase of innovation—and one of the highest-leverage opportunities at Oscar to apply AI to core healthcare workflows. You’ll build and scale decisioning systems (e.g., auto-approvals, intelligent routing, proactive guidance) that improve member and provider experience and drive meaningful cost efficiency. For PMs looking to develop as AI-first product leaders, this is a unique opportunity to work on high-stakes applications of AI in healthcare.

You will report into a Staff Product Manager.

Work Location:

This position is based in our Los Angeles (Marina del Rey) office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency:

The base pay for this role is: $163,944.00 - $215,176.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Develop product strategy: Define the vision and roadmap for Authorization Services, identifying opportunities to improve member experience, reduce provider burden, and drive payer efficiency.
• Lead discovery: Partner with Operations, Clinical, and Provider teams to deeply understand user needs, identify high-impact problems, and validate solutions.
• Execute development: Work closely with Engineering, Design, and Data Science to build and launch high-quality, scalable products, including AI-driven decisioning systems.
• Drive cross-functional collaboration: Collaborate with Operations, Legal, Compliance, and external partners to ensure solutions are operationally viable, compliant, and effectively delivered.
• Measure and iterate: Define success metrics (e.g., auto-approval rate, turnaround time, operational efficiency), generate insights with Data partners, and continuously refine the product strategy.
• Shape the future of the platform: Contribute to how AI and decisioning systems are applied across Oscar’s core insurance workflows.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Requirements:

• 6+ years of experience collaborating cross-functionally among engineers, designers, operations experts, and others in a Product Management or Product Management-adjacent role.
• 4+ years of experience in driving rigorous prioritization processes.
• 4+ years of experience with tech systems and understanding basic technology infrastructure such as backend services, database relationships, and leveraging database tools such as SQL.
• 2+ years of experience leading complex, cross-domain initiatives.
• 2+ years of experience root-causing ambiguous problems, building roadmaps towards a solution, and successfully executing against that roadmap.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Bonus points:

• Technical background or experience working on complex, technical systems.
• Experience in healthcare, particularly payer or provider workflows.
• Experience building or scaling AI/ML-driven products.

Hi, we're Oscar. We're hiring a Senior Product Manager, Authorization Services to join our Product team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Oscar is looking for a Senior Product Manager to help transform how healthcare authorizations work—one of the most complex, costly, and frustrating parts of the payer ecosystem. Today, prior authorization creates friction across the system: members face delays in care, providers navigate administrative burden, and payers incur significant operational cost. Our mission is to fundamentally redesign this experience.

You will be part of the Authorization Services team, which is rethinking utilization management from a reactive approval process into a proactive, intelligent system that guides members to the right care—while minimizing or eliminating the need for manual authorization altogether.

This is a high-impact, high-visibility role at the center of Oscar’s next phase of innovation—and one of the highest-leverage opportunities at Oscar to apply AI to core healthcare workflows. You’ll build and scale decisioning systems (e.g., auto-approvals, intelligent routing, proactive guidance) that improve member and provider experience and drive meaningful cost efficiency. For PMs looking to develop as AI-first product leaders, this is a unique opportunity to work on high-stakes applications of AI in healthcare.

You will report into a Staff Product Manager.

Work Location:

This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency:

The base pay for this role is: $163,944.00 - $215,176.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Develop product strategy: Define the vision and roadmap for Authorization Services, identifying opportunities to improve member experience, reduce provider burden, and drive payer efficiency.
• Lead discovery: Partner with Operations, Clinical, and Provider teams to deeply understand user needs, identify high-impact problems, and validate solutions.
• Execute development: Work closely with Engineering, Design, and Data Science to build and launch high-quality, scalable products, including AI-driven decisioning systems.
• Drive cross-functional collaboration: Collaborate with Operations, Legal, Compliance, and external partners to ensure solutions are operationally viable, compliant, and effectively delivered.
• Measure and iterate: Define success metrics (e.g., auto-approval rate, turnaround time, operational efficiency), generate insights with Data partners, and continuously refine the product strategy.
• Shape the future of the platform: Contribute to how AI and decisioning systems are applied across Oscar’s core insurance workflows.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Requirements:

• 6+ years of experience collaborating cross-functionally among engineers, designers, operations experts, and others in a Product Management or Product Management-adjacent role.
• 4+ years of experience in driving rigorous prioritization processes.
• 4+ years of experience with tech systems and understanding basic technology infrastructure such as backend services, database relationships, and leveraging database tools such as SQL.
• 2+ years of experience leading complex, cross-domain initiatives.
• 2+ years of experience root-causing ambiguous problems, building roadmaps towards a solution, and successfully executing against that roadmap.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Bonus points:

• Technical background or experience working on complex, technical systems.
• Experience in healthcare, particularly payer or provider workflows.
• Experience building or scaling AI/ML-driven products.

Hi, we're Oscar. We're hiring a Director, Tech Business Operations to join our Technology team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

As a Director, Tech Business Operations, you will be responsible for driving the overarching strategic direction and operational excellence for Oscar’s technology organization. This role serves as a primary advisor to technology leadership, influencing high-stakes decision-making and driving innovation through large-scale process improvements and strategic initiatives. The role works independently to oversee multi-year roadmaps and ensures alignment with enterprise-level goals. 

You will report into a Head of Tech Strategy & Operations.

Work Location:

This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency:

The base pay for this role is: $218,592.00 - $286,902.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Strategic Leadership: Orchestrate cross-functional collaboration at the executive level across Technology, Finance, and Product to architect and implement global technology strategies.
• Operational Excellence: Establish and report on high-level Technology Operations KPIs and business-aligned metrics to executive leadership and the Board.
• Roadmap & Governance: Direct the long-term evolution of technology architecture, overseeing multi-year roadmaps for tool evaluation, selection, and implementation.
• Leadership Development: Lead and scale a high-performing organization of managers and individual contributors, focusing on mentorship and professional growth.
• Crisis & Risk Management: Serve as a point of escalation for complex technical issues and proactively identify and mitigate organizational risks.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Requirements:

• Bachelor’s degree in a STEM field or 4+ years of commensurate work experience.
• 10+ years of professional experience in technology strategy, operations, or a related leadership role.
• 7+ years of experience building, coaching, and developing high-performing technical or operational teams.
• Demonstrated expertise in using data (e.g., Excel, SQL) to influence complex organizational decisions and drive investments

Bonus points:

• Advanced Degree: Master’s degree (MBA or MS in a technical field) preferred
• Industry Context: Deep expertise in the healthcare regulatory landscape (e.g., HIPAA) and experience in high-growth or public company environments
• Methodologies: Process Improvement or Lean Six Sigma certification
• Communication: Proven history of successfully briefing C-suite executives during high-pressure situations.

Hi, we're Oscar. We're hiring an Intern to join our Internal Communications Team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Internal Communications Intern will support the Communications team in creating a connected, informed, and inspired employee experience. This role is perfect for a storyteller who is passionate about company culture and wants to learn how to bridge the gap between business strategy and employee engagement.

During this internship, you will help execute key communications channels, assist with large-scale internal events, and develop content that captures Oscar's unique voice for our team. You'll work on real-life projects that impact our team members and help make our mission to change healthcare feel tangible for every employee.

You will report into the Senior Manager, Internal Communications.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The hourly pay for this role is: $27- $35 an hour. You are also eligible for employee benefits.. You are also eligible for employee benefits.

Responsibilities:

• Draft and edit compelling content for internal channels, including email newsletters, Slack announcements, intranet articles, and executive talking points.
• Assist in the planning and technical execution of company-wide forums, such as All Hands meetings, leadership Q&As, and office-specific culture events.
• Support the day-to-day management of internal platforms, ensuring information is organized, timely, and easy for employees to find.
• Assist in the production of digital assets and internal videos to make communications more engaging.
• Help monitor communication metrics and gather employee feedback to identify opportunities for continuous improvement in how we reach our teams.
• Partner with cross-functional stakeholders to communicate culture-building initiatives and business updates.
• Own and complete one high-impact summer project (e.g., refreshing an onboarding guide or launching a new Slack series) to be presented at the end of the internship.
• Perform other duties as assigned to support the Communications team.

Responsibilities

• Currently enrolled in an undergraduate or graduate program, preferably focusing on Communications, English, Public Relations, Journalism, or a related field.
• Superior writing and interpersonal skills—you know how to be professional but human.
• Foundational understanding of digital communication tools (e.g., Google Workspace, Slack).

Bonus points:

• No genius without grit. You have a relentless, can-do attitude and aren't afraid to try, fail, and iterate.
• Experience with content creation (writing, editing, design) for newsletters, blogs, or social media. Experience with basic design (Canva/Adobe) or video editing is a plus!
• Experience working in a fast-paced or high-growth environment.

Hi, we're Oscar. We're hiring a Workday Architect to join our People Systems team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Workday Architect is responsible for leading the design and management of Workday solutions across Compensation Time/Leave, and Payroll. This role requires a strategic thinker with a deep understanding of Workday functionalities and the ability to manage consultants while executing complex projects and enhancements.

You will report into the Senior Director, People Technology & Operations. 

Work Location:

This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency:

The base pay for this role is: $144,000 - $189,000 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Workday Solution Design & Stakeholder Engagement:
  • Lead the design and architecture of scalable Workday solutions across Compensation, Time/Leave and Payroll.
  • Serve as primary Workday SME, translating business requirements into effective configurations and enhancements. 
  • Ensure Workday solutions comply with data governance, audit, legal, organizational policies, and apply industry standards to elevate.
  • Identify and mitigate risks related to Workday changes and implementations.
  • Define and manage stakeholder engagement model with Payroll, including roles and responsibilities. 
  • Lead and oversee consultants, providing direction and quality assurance.

• Project Delivery & Process Improvement
  • Own planning and delivery of Workday projects and enhancements, ensuring standard project management practices are utilized to ensure successful on-time and on-budget execution 
  • Coordinate cross-functional teams to support successful integration and adoption
  • Drive process improvements and automation to improve efficiency and user experience
  • Stay current on Workday release and best practices to maximize platform value
  • Provide regular project status updates and stakeholder communication. 
  • Identify opportunities for process improvements and automation within Workday modules to enhance efficiency and user experience. 
  • Conduct regular meetings with stakeholders to review project progress, gather feedback, and address any concerns.
  • Compliance with all applicable laws and regulations. 
  • Other duties as assigned. 

Requirements:

• 6+ years of combined configuration experience across Compensation, Time, and Payroll. 
• Experience managing and delivering complex Workday projects and enhancements.
• Experience managing and developing a direct report(s)
• Ability to engage and influence stakeholders across levels of the organization.

Bonus points:

• Workday certification(s) in relevant modules is highly desirable.

Hi, we're Oscar. We're hiring a Workday Architect to join our People Systems team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Workday Architect is responsible for leading the design and management of Workday solutions across Compensation Time/Leave, and Payroll. This role requires a strategic thinker with a deep understanding of Workday functionalities and the ability to manage consultants while executing complex projects and enhancements.

You will report into the Senior Director, People Technology & Operations. 

Work Location:

This position is based in our Tempe, AZ office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency:

The base pay for this role is: $129,600 - $170,100 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Workday Solution Design & Stakeholder Engagement:
  • Lead the design and architecture of scalable Workday solutions across Compensation, Time/Leave and Payroll.
  • Serve as primary Workday SME, translating business requirements into effective configurations and enhancements. 
  • Ensure Workday solutions comply with data governance, audit, legal, organizational policies, and apply industry standards to elevate.
  • Identify and mitigate risks related to Workday changes and implementations.
  • Define and manage stakeholder engagement model with Payroll, including roles and responsibilities. 
  • Lead and oversee consultants, providing direction and quality assurance.

• Project Delivery & Process Improvement
  • Own planning and delivery of Workday projects and enhancements, ensuring standard project management practices are utilized to ensure successful on-time and on-budget execution 
  • Coordinate cross-functional teams to support successful integration and adoption
  • Drive process improvements and automation to improve efficiency and user experience
  • Stay current on Workday release and best practices to maximize platform value
  • Provide regular project status updates and stakeholder communication. 
  • Identify opportunities for process improvements and automation within Workday modules to enhance efficiency and user experience. 
  • Conduct regular meetings with stakeholders to review project progress, gather feedback, and address any concerns.
  • Compliance with all applicable laws and regulations. 
  • Other duties as assigned. 

Requirements:

• 6+ years of combined configuration experience across Compensation, Time, and Payroll. 
• Experience managing and delivering complex Workday projects and enhancements.
• Experience managing and developing a direct report(s)
• Ability to engage and influence stakeholders across levels of the organization.

Bonus points:

• Workday certification(s) in relevant modules is highly desirable.

Hi, we're Oscar. We're hiring a Director to join our Finance Transformation team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Director, Finance Transformation is a senior leadership role responsible for defining and spearheading the long-term strategic roadmap for finance processes, systems, and performance across the organization. This role will be accountable for the overall vision, governance, and successful integration of transformation efforts into the company's broader financial health. This role involves high-level strategic planning, senior stakeholder influence, and building a high-performing team to deliver scalable financial infrastructure.

You will report into the Chief Accounting Officer.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $180,504- $236,911 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities:

• Define and own the multi-year Finance Transformation roadmap, ensuring it scales with organizational growth and aligns with enterprise-level financial objectives.
• Act as a key advisor to the CFO and senior leadership, driving alignment across IT, Operations, and Business Units to ensure transformation efforts support overall company strategy.
• Lead the design and implementation of global Target Operating Models (TOM) to optimize large-scale operations and drive long-term performance improvements.
• Oversee comprehensive, organization-wide change management strategies, ensuring the Finance function and broader business units adapt successfully to new systems and processes.
• Accountable for the successful delivery of a portfolio of transformation projects, including budget approval, resource allocation, and ROI tracking.
• Establish and enforce standards for financial process optimization and efficiency, ensuring all improvements meet regulatory and internal policy requirements.
• Maintain ultimate accountability for compliance with all applicable laws, regulations, and internal audit requirements within the transformation scope.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 10+ years of professional experience in finance, accounting, or business strategy
• Bachelor's degree in finance, accounting, or business administration
• 8+ years of experience in project and portfolio management, specifically leading large-scale finance transformation programs.
• 5+ years of experience leading complex financial systems implementations (e.g., Workday Financials) and applying advanced change management principles.

Bonus points:

• Master's degree in finance, accounting or business strategy; or MBA strongly preferred
• Extensive experience leading and developing high-performing teams and working collaboratively across an executive suite.
• Proven track record in a senior position within a health insurance or highly regulated environment.
• Workday Financial training certifications and experience with global, multi-entity implementations

Hi, we're Oscar. We're hiring a Senior Analyst, Data Analytics, SIU to join our SIU team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Senior Analyst, Data Analytics, SIU partners across the organization to manage inefficiencies in the business. You will support teams in scoping, analyzing and monitoring performance of important financial and utilization metrics in service of our goals. The Senior Analyst, Data Analytics collaborates independently with stakeholders to define key questions and scope analyses. They may at times be called upon to speak to prepared analysis both internally and externally. This work aims to reduce medical waste and deliver more affordable and higher-quality health care for Oscar's members.

You will report into the Manager, SIU Data Analytics & Reporting.

Work Location: This is a remote position, open to candidates who reside in: Arizona, Florida, Georgia, Illinois, Iowa, Kansas, Michigan, Missouri, Nebraska, New Jersey, New York, North Carolina, Ohio, Pennsylvania, South Carolina, Tennessee, Texas and Virginia. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area.

If you live within commutable distance to our New York City office (in Hudson Square) or our Tempe office (off the 101 at University Ave), you will be expected to come into the office at least three days each week. Otherwise, this is a remote / work-from-home role.  Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. 

Pay Transparency: The base pay for this role in the states of New Jersey and New York is: $86,628 - $109,761 per year. The base pay for this role in all other locations is: $75,265 - $98,785 per year.  You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

You must be currently authorized to work in the United States on a full-time basis. Oscar will not sponsor applicants for this role.

Responsibilities:

• Analyze data to support business teams in making better informed, data-driven decisions
• Use data to tell a story that non-technical colleagues can understand, including packaging and presenting findings in a clear, concise and compelling manner
• Oversee the creation and maintenance of essential operational and analytical dashboards, and update and enhance them as our user's needs evolve
• Create models and tools that produce relevant insights to identify inefficiencies and generate insights to remove inefficiencies
• Collaborate across the organization to identify actions to achieve improvements and monitor initiative impact
• Support other strategic projects as assigned to meet business needs
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 1+ years of technical work experience using analytical tools and writing analytical reports
• 1+ years demonstrated ability to work with large datasets and distill analyses into relevant insights with a structured and systematic thought process
• Strong communication skills, verbal and written, around business reporting impact and requirements, as demonstrated by experience on at least 2 reporting projects requiring communication between technical and non-technical users
• Experience in SQL, with the ability to filter, aggregate, and build CTEs, or proficiency in R or Python, including experience with Pandas, for loops, and statistical tests
• Proficiency in Google Sheets or Excel skills, with ability to use VLookup, nested if statements and connected Sheets
• 1+ years experience in healthcare, finance or the insurance industry

Bonus points:

• 1+ years experience in preparing healthcare analytics and reporting
• 1+ years experience managing value-based contracts at a payer or a provider organization (ACO, CIN, MSO)
• 1+ years experience developing dashboards and working with Looker, or other business intelligence/data visualization tools
• Exposure to healthcare contract negotiations, risk adjustment, ACA marketplace, quality of care, and/or population health experience

Hi, we're Oscar. We're hiring a Director, Managed Business Services to join our team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

You will be the primary architect of our global outsourcing strategy and be responsible for the end-to-end health of our outsourced ecosystems. This service covers multiple contact center, business process and configuration functions and works with multiple vendors across several countries. This strategic leadership role designs, implements, and governs external operations to ensure they align with company quality and compliance standards, cost objectives, and customer experience goals.

You will report into the SVP, Insurance Operations

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $163,944 - $215,176 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities:

• Lead the ongoing analysis and cross-functional framework to determine which business functions are optimized for outsourcing versus internal retention.
• Design and execute an operating model that supports scalability, ongoing risk mitigation, and the execution of critical business initiatives across a matrixed organization.
• Drive core business transformation by identifying emerging marketplace trends and shifting the outsourcing model from transactional tasks to transformational outcomes.
• Align service provider visions with long-term corporate goals to ensure flexibility and growth as market demands change.
• Drive the end to end selection process, in partnership with Procurement and operational leaders, including RFP leadership, vendor vetting, and onboarding of partners that align with company scale and culture.
• Partner closely with Procurement to identify and execute optimal Master Service Agreements (MSAs) and Statements of Work (SOWs) while monitoring value delivery and ROI.
• Negotiate matters of significance with senior management and external executives to ensure favorable commercial terms and operationally effective programs.
• Ensure the establishment and monitoring of rigorous Service Level Agreements (SLAs) and Key Performance Indicators (KPIs) focused on financial accuracy, productivity, and member experience.
• Perform ongoing operational governance by preparing consolidated performance reports that provide actionable insights and root-cause identification for issues.
• In partnership with finance, track ROI on outsourcing initiatives. Ensure meticulous billing analysis and the identification of opportunities for long-term cost savings.
• Set and enforce rigorous standards for all offshore and nearshore sites to ensure total adherence to HIPAA, CMS regulations, SOC2, and data privacy requirements.
• Partner with internal Audit, Security, and Compliance departments to lead the operational response to any vendor-side audits or data incidents.
• Lead the transition and change management of new work streams, including the creation of documentation, training protocols, and workflow design.
• Act as the primary bridge between internal departments and external partners to ensure seamless knowledge transfer and brand consistency.
• Create an attractive value proposition for vendor staff to minimize turnover, preserve institutional knowledge, and ensure external teams are educated on company priorities.

Requirements:

• Bachelor's Degree in Business, Operations or relevant field
• 10+ years in Insurance Operations
• 8+ years working with teams in multiple locations and within multiple disciplines
• 8+ years of coaching and developing leading cross-functional people and teams
• 6+ years of experience in LEAN, Six Sigma, or other improvement methodologies
• 6+ years of experience leading large-scale implementations or expansion implementations across multiple site locations or business units
• 5+ years of experience in procurement processes, including negotiating and contracting BPO services
• 5+ years managing 3rd-party BPO/ITO relationships for major functions in insurance operations.
• Strong legal and commercial acumen with experience in multi-million dollar contract negotiations.
• Ability to influence internal/external and onshore/offshore leadership

Bonus points:

• MBA or relevant advanced degree
• 10+ years of experience on Insurance Payer side
• Advanced experience with Procurement or Contract Management functions
• Advanced experience in healthcare
• Experience managing international teams across different time zones (APAC, LATAM, EMEA).
• Proven track record of scaling an outsourcing program from "scratch" to a global footprint.

Hi, we're Oscar. We're hiring an Intern to join our Insurance Marketing Team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

We are seeking a proactive and detail-oriented Marketing Intern to support the launch of two new brands under the Oscar Health umbrella. This is a hands-on opportunity to contribute to high-impact initiatives across multiple marketing channels while collaborating closely with cross-functional teams. You'll gain exposure to brand building from the ground up and take ownership of meaningful projects that directly influence go-to-market success.

This includes maintaining status documentation, coordinating cross-functional meetings, facilitating feedback sessions, managing timelines, and capturing clear meeting notes along with actionable next steps.

You will report into the Head of Lucie Marketing.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The hourly pay for this role is: $27- $35 an hour. You are also eligible for employee benefits.

Responsibilities:

• Support the development and execution of the new brands and take ownership of key marketing initiatives and tactics
• Assist in planning and executing marketing campaigns across digital and offline channels
• Creating and refining sales materials (pitch decks, one-pagers, case studies)
• Assisting with CRM strategies and execution, including email campaigns and automation workflows
• Conduct market and/or competitor research to stay on top of industry trends
• Collaborate with design, product, sales, and operations teams to ensure cohesive brand execution
• Track and report on campaign performance, providing insights and recommendations
• Partner with Compliance to review all materials
• Other duties as assigned

Requirements:

• Experience in all Google products (documents, slides, sheets)
• Experience communicating with internal and external stakeholders
• Project management experience
• Strong written and verbal communication skills
• Highly organized with strong attention to detail
• Self-starter with the ability to manage multiple projects and meet deadlines
• Familiarity with marketing tools (e.g., CRM platforms, email marketing tools, CMS) is a plus
• Analytical mindset with a willingness to learn and adapt

Bonus points:

• Currently pursuing or recently completed a degree in Marketing, Business, Communications, or a related field
• Healthcare or healthcare related experience including healthcare consulting, healthcare operations, healthcare finance, or related field
• Experience in fast-paced environments

Travel required? (if so, list % of time expected - ex: Up to 5%)

• No travel required
• NYC in-office presence required 3x a week (preference Tuesday, Wednesday and Thursday)

Hi, we're Oscar. We're hiring a Senior Security Engineer 1, GRC to join our Security Team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Principal GRC Engineer designs and operates the systems that enable continuous security assurance, deep risk visibility, and scalable regulatory compliance. Rather than managing documentation or preparing for audits, this role engineers the infrastructure that allows the organization to demonstrate security and compliance continuously through automation, telemetry, and self-evidencing controls.

Operating at the intersection of security engineering, platform engineering, risk management, and regulatory assurance, you will embed governance and control validation directly into how systems are built and operated. By connecting controls, operational telemetry, engineering workflows, and risk signals, you will surface patterns and relationships that traditional GRC programs cannot see, creating a feedback loop where security intelligence continuously informs engineering guardrails and platform architecture.

You will report into the Sr. Manager GRC.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. 

Pay Transparency: The base pay for this role is: $163,944 per year - $215,176 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Design systems that continuously measure and validate security controls through operational telemetry, automated evidence generation, and control health monitoring.
• Build automation and orchestration across security tools, cloud platforms, and engineering systems to eliminate manual compliance processes and reduce audit overhead.
• Translate governance expectations into machine-enforceable guardrails embedded within infrastructure platforms, CI/CD pipelines, and engineering workflows.
• Apply automation, orchestration, and AI-assisted capabilities to scale governance workflows, enabling intelligent analysis and adaptive control systems.
• Architect control and telemetry pipelines where operational systems produce the evidence required for regulatory assurance and audit readiness.
• Compliance with all applicable laws and regulations 
• Other duties as assigned 

Requirements:

• 4+ years experience in Technology related field. 
• 4+ years experience in Security Engineering.

Bonus points:

• Familiarity with industry standards and compliance frameworks (such as SOC, SOX., NIST, HIPAA) and experience in ensuring organizational adherence to these standards.
• Certifications such as CISSP, CISM, CISA, CEH, or vendor-specific certifications.
• Proficiency in managing security projects, including planning, execution, and successful delivery within timelines and budgets.
• 4+ years of experience in Security Engineering, DevSecOps, or Site Reliability Engineering (SRE), with at least 3 years specifically focused on GRC automation or internal security tooling.

Hi, we're Oscar. We're hiring a Senior Analyst, Regulatory Operations to join our Regulatory team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Sr. Regulatory Analyst is an important member of the Regulatory Operations team responsible for project managing and supporting discrete tasks to ensure Oscar is compliant with federal and state product filing requirements. You will work with internal Oscar teams and interfaces with our external regulators.

You will report into the Senior Manager, Regulatory Operations.

Work Location: This is a remote position, open to candidates who reside in: Arizona, California, Florida, Georgia, Illinois, Iowa, Kansas, Michigan, Missouri, Nebraska, New Jersey, New York, North Carolina, Ohio, Pennsylvania, South Carolina, Tennessee, Texas and Virginia. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area.

Pay Transparency: The base pay for this role in the states of New Jersey and New York is: $38.22 - $50.16 per hour. The base pay for this role for all other locations is: $34.39 - $45.14 per hour. You are also eligible for employee benefits and monthly vacation accrual at a rate of 15 days per year.

Responsibilities:

• Manage the preparation and filing of Oscar's commercial insurance products through the annual Form & Binder Filings for assigned states and regions, serving as an advisor to teams
• Develop processes for internal tracking and monitoring annual and ad hoc filings with diverse teams, including maintaining a repository of previously received objections to decrease YOY objection totals
• Build and support successful relationships with regulatory bodies, including state insurance regulators (e.g., DMHC in California, Arizona Department of Insurance, Texas Department of Insurance), state-based exchanges (e.g., Covered California), and federal insurance regulators (CMS, CCIIO, etc.)
• Serve as a subject matter expert on assigned states and contribute to the development of a repository of internal procedural guides on annual filing obligations to support teams and retain institutional knowledge
• Track and share filing objections received and guide overall resolution together with impacted teams
• Develop sustainable processes which simplify our growing team's outputs while ensuring high quality deliverables
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree or commensurate experience
• 1+ years of SERFF and HIOS experience
• Demonstrated project management skills

Bonus points:

• Familiarity with ACA marketplace plans, rules and regulations

Hi, we're Oscar. We're hiring a Senior Manager, Technical Accounting to join our Accounting team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Senior Manager, Technical Accounting, would lead our technical accounting work. You will work cross-functionally to understand and to provide technical accounting guidance on new or complex transactions and corresponding financial disclosures. You will develop, enhance, and maintain accounting policies and ensure policies reflect current practices and operations of the business and are up-to-date and compliant with existing and newly adopted accounting standards and regulations.

You will report into the Associate Director, SEC Reporting and Technical Accounting.

Work Location: 

This is a remote position, open to candidates who reside in: Boston, MA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Lead our technical accounting work required under US GAAP and statutory reporting and partner with the Tax Team to ensure tax aspects are considered.
• Partner with teams, and external partners and/or consultants, to:
  • provide technical accounting expertise to support new transactions and new or evolving business arrangements, and
  • prepare technical accounting analysis on complex accounting issues.
• Create our accounting policies.
• Oversee, and apply new accounting pronouncements applicable to the Company.
• Work with the Company's external auditors on technical accounting matters.
• Help review financial disclosures in SEC and statutory filings related to our accounting policies and impact of new accounting pronouncements.
• Develop relationships with cross-functional teams to understand broad goals and provide accounting guidance and best practice recommendations to allow process improvements.
• Perform ad-hoc technical accounting research and analysis to support special projects.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 6+ years of relevant experience.
• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• Certified Public Accountant licensure (CPA).
• 2+ years of experience with US-based insurance companies.
• 2+ years of practical experience in financial reporting.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience working collaboratively across the organization.
• 4+ years of experience with US-based insurance companies.
• 4+ years of practical experience in financial reporting.
• 6+ year in public accounting

Hi, we're Oscar. We're hiring a Senior Manager, Technical Accounting to join our Accounting team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Senior Manager, Technical Accounting, would lead our technical accounting work. You will work cross-functionally to understand and to provide technical accounting guidance on new or complex transactions and corresponding financial disclosures. You will develop, enhance, and maintain accounting policies and ensure policies reflect current practices and operations of the business and are up-to-date and compliant with existing and newly adopted accounting standards and regulations.

You will report into the Associate Director, SEC Reporting and Technical Accounting.

Work Location: 

This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Lead our technical accounting work required under US GAAP and statutory reporting and partner with the Tax Team to ensure tax aspects are considered.
• Partner with teams, and external partners and/or consultants, to:
  • provide technical accounting expertise to support new transactions and new or evolving business arrangements, and
  • prepare technical accounting analysis on complex accounting issues.
• Create our accounting policies.
• Oversee, and apply new accounting pronouncements applicable to the Company.
• Work with the Company's external auditors on technical accounting matters.
• Help review financial disclosures in SEC and statutory filings related to our accounting policies and impact of new accounting pronouncements.
• Develop relationships with cross-functional teams to understand broad goals and provide accounting guidance and best practice recommendations to allow process improvements.
• Perform ad-hoc technical accounting research and analysis to support special projects.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 6+ years of relevant experience.
• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• Certified Public Accountant licensure (CPA).
• 2+ years of experience with US-based insurance companies.
• 2+ years of practical experience in financial reporting.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience working collaboratively across the organization.
• 4+ years of experience with US-based insurance companies.
• 4+ years of practical experience in financial reporting.
• 6+ year in public accounting

Hi, we're Oscar. We're hiring a Senior Manager, Technical Accounting to join our Accounting team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Senior Manager, Technical Accounting, would lead our technical accounting work. You will work cross-functionally to understand and to provide technical accounting guidance on new or complex transactions and corresponding financial disclosures. You will develop, enhance, and maintain accounting policies and ensure policies reflect current practices and operations of the business and are up-to-date and compliant with existing and newly adopted accounting standards and regulations.

You will report into the Associate Director, SEC Reporting and Technical Accounting.

Work Location: 

This is a remote position, open to candidates who reside in: Dallas, TX. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Lead our technical accounting work required under US GAAP and statutory reporting and partner with the Tax Team to ensure tax aspects are considered.
• Partner with teams, and external partners and/or consultants, to:
  • provide technical accounting expertise to support new transactions and new or evolving business arrangements, and
  • prepare technical accounting analysis on complex accounting issues.
• Create our accounting policies.
• Oversee, and apply new accounting pronouncements applicable to the Company.
• Work with the Company's external auditors on technical accounting matters.
• Help review financial disclosures in SEC and statutory filings related to our accounting policies and impact of new accounting pronouncements.
• Develop relationships with cross-functional teams to understand broad goals and provide accounting guidance and best practice recommendations to allow process improvements.
• Perform ad-hoc technical accounting research and analysis to support special projects.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 6+ years of relevant experience.
• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• Certified Public Accountant licensure (CPA).
• 2+ years of experience with US-based insurance companies.
• 2+ years of practical experience in financial reporting.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience working collaboratively across the organization.
• 4+ years of experience with US-based insurance companies.
• 4+ years of practical experience in financial reporting.
• 6+ year in public accounting

Hi, we're Oscar. We're hiring a Senior Manager, Technical Accounting to join our Accounting team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Senior Manager, Technical Accounting, would lead our technical accounting work. You will work cross-functionally to understand and to provide technical accounting guidance on new or complex transactions and corresponding financial disclosures. You will develop, enhance, and maintain accounting policies and ensure policies reflect current practices and operations of the business and are up-to-date and compliant with existing and newly adopted accounting standards and regulations.

You will report into the Associate Director, SEC Reporting and Technical Accounting.

Work Location: 

This is a remote position, open to candidates who reside in: Atlanta, GA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Lead our technical accounting work required under US GAAP and statutory reporting and partner with the Tax Team to ensure tax aspects are considered.
• Partner with teams, and external partners and/or consultants, to:
  • provide technical accounting expertise to support new transactions and new or evolving business arrangements, and
  • prepare technical accounting analysis on complex accounting issues.
• Create our accounting policies.
• Oversee, and apply new accounting pronouncements applicable to the Company.
• Work with the Company's external auditors on technical accounting matters.
• Help review financial disclosures in SEC and statutory filings related to our accounting policies and impact of new accounting pronouncements.
• Develop relationships with cross-functional teams to understand broad goals and provide accounting guidance and best practice recommendations to allow process improvements.
• Perform ad-hoc technical accounting research and analysis to support special projects.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 6+ years of relevant experience.
• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• Certified Public Accountant licensure (CPA).
• 2+ years of experience with US-based insurance companies.
• 2+ years of practical experience in financial reporting.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience working collaboratively across the organization.
• 4+ years of experience with US-based insurance companies.
• 4+ years of practical experience in financial reporting.
• 6+ year in public accounting

Hi, we're Oscar. We're hiring a Senior Manager, Technical Accounting to join our Accounting team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Senior Manager, Technical Accounting, would lead our technical accounting work. You will work cross-functionally to understand and to provide technical accounting guidance on new or complex transactions and corresponding financial disclosures. You will develop, enhance, and maintain accounting policies and ensure policies reflect current practices and operations of the business and are up-to-date and compliant with existing and newly adopted accounting standards and regulations.

You will report into the Associate Director, SEC Reporting and Technical Accounting.

Work Location: This position is based in our Tempe, AZ office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Lead our technical accounting work required under US GAAP and statutory reporting and partner with the Tax Team to ensure tax aspects are considered.
• Partner with teams, and external partners and/or consultants, to:
  • provide technical accounting expertise to support new transactions and new or evolving business arrangements, and
  • prepare technical accounting analysis on complex accounting issues.
• Create our accounting policies.
• Oversee, and apply new accounting pronouncements applicable to the Company.
• Work with the Company's external auditors on technical accounting matters.
• Help review financial disclosures in SEC and statutory filings related to our accounting policies and impact of new accounting pronouncements.
• Develop relationships with cross-functional teams to understand broad goals and provide accounting guidance and best practice recommendations to allow process improvements.
• Perform ad-hoc technical accounting research and analysis to support special projects.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 6+ years of relevant experience.
• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• Certified Public Accountant licensure (CPA).
• 2+ years of experience with US-based insurance companies.
• 2+ years of practical experience in financial reporting.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience working collaboratively across the organization.
• 4+ years of experience with US-based insurance companies.
• 4+ years of practical experience in financial reporting.
• 6+ year in public accounting

Hi, we're Oscar. We're hiring a Senior Manager, Technical Accounting to join our Accounting team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Senior Manager, Technical Accounting, would lead our technical accounting work. You will work cross-functionally to understand and to provide technical accounting guidance on new or complex transactions and corresponding financial disclosures. You will develop, enhance, and maintain accounting policies and ensure policies reflect current practices and operations of the business and are up-to-date and compliant with existing and newly adopted accounting standards and regulations.

You will report into the Associate Director, SEC Reporting and Technical Accounting.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $149,040 - $195,615 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Lead our technical accounting work required under US GAAP and statutory reporting and partner with the Tax Team to ensure tax aspects are considered.
• Partner with teams, and external partners and/or consultants, to:
  • provide technical accounting expertise to support new transactions and new or evolving business arrangements, and
  • prepare technical accounting analysis on complex accounting issues.
• Create our accounting policies.
• Oversee, and apply new accounting pronouncements applicable to the Company.
• Work with the Company's external auditors on technical accounting matters.
• Help review financial disclosures in SEC and statutory filings related to our accounting policies and impact of new accounting pronouncements.
• Develop relationships with cross-functional teams to understand broad goals and provide accounting guidance and best practice recommendations to allow process improvements.
• Perform ad-hoc technical accounting research and analysis to support special projects.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 6+ years of relevant experience.
• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• Certified Public Accountant licensure (CPA).
• 2+ years of experience with US-based insurance companies.
• 2+ years of practical experience in financial reporting.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience working collaboratively across the organization.
• 4+ years of experience with US-based insurance companies.
• 4+ years of practical experience in financial reporting.
• 6+ year in public accounting

Hi, we're Oscar. We're hiring a Senior Manager, Speciality / Ancillary Products to join our Insurance Product Development team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Senior Manager, Speciality / Ancillary Solutions is accountable for the strategy, design, execution and performance of the ancillary product portfolio, with a primary focus on dental and vision. This role owns the end-to-end lifecycle of ancillary insurance products including product strategy, regulatory execution, third party vendor implementation leadership and management post launch optimization across the individual market.

You will report into the Vice President, Insurance Product Innovation and Development

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role is: $149,040 - $195,615 per year in New Jersey, New York, and California. The base pay for all other locations is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

Ancillary Product Strategy & Portfolio Management

• In partnership with leader, drives the ancillary product strategy and roadmap across dental, vision and other ancillary offerings (e.g. hearing, fitness, over the counter benefits, wellness and other insurance add-on products)

• Owns the full end-to-end lifecycle of ancillary products, including dental and vision insurance offerings, from ideation and benefit design through launch, performance management, and ongoing optimization

• Build and manage business cases for new and existing products, including financial modeling, membership projections, and ongoing performance tracking against goals.

• Analyze product performance using financial and membership metrics to forecast results, identify risks and opportunities, and inform decision-making.

• Lead benefit design for ancillary products, including augmenting existing offerings, remediating underperforming designs, and introducing new benefit structures for specific consumer populations, based on performance, member needs, and market dynamics

• Contribute to annual planning, roadmap development, and prioritization for ancillary products

Vendor Implementation Lead & Management

• Business lead for end to end implementation of ancillary vendors, serving as the primary product DRI and escalation point for dental and vision vendors and provide oversight for ancillary vendors

• Define and manage vendor requirements, SLAs, KPIs and performance scorecards

• Partner with procurement, legal and compliance on vendor selection, contracting, renewals and performance governance

• Drive timely issue resolution and root cause remediation with vendors to prevent repeat issues

• Serves as a member of the Joint Operating Committee (JOC) for ancillary products, in partnership with Network, and leadership, including agenda setting, performance reviews, issue tracking, and follow-through on commitments

• Identify risks, gaps, and opportunities across benefit design, product performance, and execution, including recommendation of corrective actions

Execution, Filings & Regulatory Alignment

• Partner with Actuarial and Finance teams to evaluate pricing, unit economics, and profitability tradeoffs, to inform benefit and portfolio decisions

• Collaborate with Regulatory and Legal teams to ensure ancillary products comply with federal and state requirements and are filed, updated, and approved as needed

• Oversee ancillary product QA, attestations and final sign off prior to filing submissions

• Ensure compliance with all applicable laws, regulations, and internal governance standards

Cross Functional Leadership & Governance

• Act as the single accountable product owner for ancillary benefits- coordinating across teams

• Translate vendor capabilities and regulatory constraints into clear product requirements

• Influence senior leaders with clear data-driven recommendations and risk assessments

Post Launch Performance & Optimization

• Develop and maintain regular performance reporting and product look-backs, assessing financial, operational, clinical, and member experience outcomes

• Use analytics and business intelligence tools (e.g., Looker) to pull, analyze, and interpret data related to utilization, cost, engagement, retention, and vendor performance

• Carry forward learnings to future cycles to improve scalability, reduce risk and enhance member outcomes

Data Driven Decision Making

• Leverage enrollment, utilization, cost, quality and vendor performance data to inform ancillary product strategy

• Identify trends and risks early and proactively adjust product or vendor strategies

• Compliance with all applicable laws and regulations

• Other duties as assigned

Requirements:

• 6+ years of experience developing, managing, or supporting commercial insurance products, with direct ownership of ancillary (dental, vision, supplemental health) offerings, with Strong understanding of regulatory requirements impacting ancillary benefits 

• 5+ years of expertise in Dental and Vision product design and vendor implementation

• 4+ years of Proven experience managing delegated vendors and complex operational partnerships

• 4 + years experience with ACA, including individual market place and small group products

• 3+ years of experience with product lifecycle management for ancillary offerings

• 3+  years experience making data-driven decision and using business intelligence tools to analyze product performance

• Travel up to 25% of the time

Bonus points:

• Bachelor’s degree in business, healthcare, analytics, or related field

• Experience with ancillary insurance products (e.g., dental, vision, supplemental benefits)

• Proficiency with business intelligence tools, experience with SQL, Excel, or similar tools

• Experience supporting or participating in Joint Operating Committee or vendor governance forums

Hi, we're Oscar. We're hiring an Senior Manager, Multicultural Insurance Solutions to join our Insurance Product Development team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Senior Manager, Multicultural Insurance Solutions is responsible for the end-to-end strategy, design, execution and performance of multicultural products that address the needs of diverse member populations across language, culture, ethnicity, geography and socioeconomic status across the individual and employer-subsidized markets. This role is accountable for ensuring offerings are culturally relevant, affordable, compliant, and operationally scalable and owns multicultural product strategy from insight generation through implementation post launch performance, ensuring offerings are culturally responsive, regulatory-compliant, operationally scalable and measurably effective.

You will report into the Vice President, Insurance Product Innovation and Development

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role is: $149,040 - $195,615 per year in New Jersey, New York, and California. The base pay for all other locations is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Product Strategy & Design

  • Own the end-to-end lifecycle of multicultural insurance products from ideation and benefit design through launch, performance management, and optimization informed by population demographics, utilization patterns, health disparities, member feedback and market specific needs

  • Define product intents and value propositions tailored to culturally and linguistically diverse populations

  • Translate insights into scalable product designs, including benefit structures, programs, services and engagement models

  • Ensure product strategies align to enterprise growth, equity, quality and affordability objectives

  • Lead benefit design for multicultural plans, including augmenting existing offerings, remediating underperforming designs, and introducing new benefit structures informed by population needs and product performance

  • Collaborate across internal partners on all necessary aspects of our multicultural products  

  • Contribute to annual planning, roadmap development, and prioritization for multicultural products

   

  Analytics & Insight Generation

  • Leverage quantitative and qualitative analytics to identify unmet needs, disparities and opportunities across multicultural populations

  • Partner with data teams to develop models, dashboards and KPIs for relevant attributes

  • Use data to inform prioritization, investment decisions and trade off analyses

  • Translate insights into clear recommendations for senior leadership and cross functional partners

   

  Execution &  Implementation 

  • Build and manage business cases for new and existing products, including financial modeling, membership projections, and ongoing performance tracking against goals

  • Ensure product designs and enhancements consider the end to end consumer journey and experience, including enrollment, access to care, ongoing engagement, and member support, with attention to cultural needs

  • Support go to market planning in partnership with growth, sales, and marketing teams, ensuring product positioning and materials are culturally and linguistically appropriate

  • Lead cross-functional execution for multicultural product enhancements, issue resolution, and implementation activities

  • Act as the final product owner accountable for readiness prior to launch

   

  Regulatory, Compliance & Equity Alignment

  • Work closely with regulatory and legal teams to ensure multicultural plans comply with federal and state requirements, including language access and nondiscrimination standards and are filed, updated, and approved as needed

  • Embed health equity principles into product governance, documentation and approvals

   

  Performance & Continuous Improvement

  • Measure product effectiveness through outcomes such as access, engagement, utilization, quality, experience and cost, identify gaps and lead remediation efforts

  • Conduct retrospectives alongside the Strategic Implementation team to capture learnings and drive continuous improvement

  • Analyze product performance using financial and membership metrics to forecast results, identify risks and opportunities, and inform decision-making

   

  Cross Functional Leadership & Influence

  • Serve as the multicultural product SME and strategic cross functional partner, embedding cultural competence into product design standards and decision making and communicating complex product strategies and performance insights clear to executive leaders

  • Other duties as assigned

  • Compliance with all applicable laws and regulations

  
  
  

Requirements:

• 6+ years of experience developing, managing, or supporting commercial insurance products, including multicultural offerings

• 5+ years experience with ACA, including individual market place and small group products

• 3+ years of Demonstrated ownership of end to end product lifecycle management

• 5+ years Demonstrated experience designing and executing multicultural, equity-focused or population specific products

• 3+ years Experience working cross-functionally in highly regulated and sometimes vague environments

• 3+ years experience making analytical and data-driven decisions

• 4+ years of experience managing cross functional stakeholders and initiatives 

• Ability to speak fluent Spanish

• Travel up to 25% of the time

Bonus points:

• Bachelor’s degree in business, healthcare, public policy, analytics, or related field

• Experience developing or managing products for multicultural, multilingual, or underserved populations

• Spanish language proficiency strongly preferred

• Experience with business intelligence tools, experience with SQL, Excel, or similar tools

• Experience incorporating affordability, access, and cultural considerations into product strategy and execution

Hi, we're Oscar. We're hiring a Senior Manager, Individual and Family Plan Insurance Solutions to join our Insurance Product Development team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Senior Manager, Individual and Family Plan Insurance Solutions is a hands-on product owner accountable for end-to-end plan outcomes for assigned IFP markets. This role owns plan strategy, detailed design, filing execution, launch readiness, and post-launch performance, and is directly responsible for plan quality and stability once live. This individual is also directly accountable for health solution execution from product development to filing, launch, and post-launch performance, while also being directly accountable for plan readiness, quality, and issue remediation.

You will report into the Vice President, Insurance Product Innovation and Development

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role is: $149,040 - $195,615 per year in New Jersey, New York, and California. The base pay for all other locations is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

Strategy & Plan Design

• Lead end-to-end plan design, including benefits, cost-sharing, and networks while balancing member experience with affordability and operational constraints

• Translate market strategy, regulatory requirements, and growth objectives into detail executable designs

• Proactively identify design opportunities or risks based on market dynamics and performance insights

• Use quantitative and qualitative data to drive design decisions and proactively identify market risks or opportunities.

Execution & Filing Ownership

• Serve as the primary product owner for assigned market filings, coordinating cross-functionality with Actuarial, Regulatory, Compliance, Operations and Technology teams to ensure on-time accurate delivery

• Ensure all designs are accurately reflected in filings, systems, and member-facing materials

Quality, Approvals & Accountability

• Lead plan-level Quality Assurance (QA) and readiness reviews; identify and remediate design or execution defects

• Escalate material risks with clear recommendations and supporting analysis

Post-Launch Performance

• Partner with Market Directors and Actuarial to monitor plan performance post-launch

• Identify underperformance, conduct root-cause analysis, and drive corrective actions

• Feed learnings forward into future plan cycles and portfolio discussions

Requirements:

• 6+ years of product management experience, preferably in IFP and Employer-Subsidized products

• 5+ years of management experience in cross-functional environment (e.g., finance, consulting, health insurance)

• 4+ years of experience owning plan design and regulatory filings

• 3+ years of experience and strong proficiency with Excel and SQL required to manipulate and analyze data

• Travel up to 25% of the time

Bonus points:

• BS/BA degree in a quantitative or healthcare field such as Business, Healthcare, Economics, Mathematics, Statistics, Actuarial Science and Finance or equivalent years of experience.

• 6+ years in a fast-paced, cross-functional environment such as consulting, finance, economics, or business development

• Prior experience in Health Insurance (Individual and/or Small Employer) and/or Healthcare industry 

• Experience with R, and/or Python

• Demonstrated ability to navigate ambiguity to drive to outcomes, work with large datasets and distill analyses into actionable business insights with a structured and systematic thought process

Hi, we're Oscar. We're hiring an Senior Manager, Clinical & Disease Specific Insurance Solutions to join our Insurance Product Development team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Senior Manager, Clinical & Disease Specific Insurance Solutions, owns the end to end lifecycle of insurance products designed to serve members with specific clinical needs or disease profiles (e.g., diabetes, COPD). This role is accountable for product strategy, benefit design, launch, performance management, and ongoing optimization, ensuring plans improve access, remove barriers to care, improve clinical outcomes, and affordability, while remaining compliant and operationally scalable.

You will report into the Vice President, Insurance Product Innovation and Development

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role is: $149,040 - $195,615 per year in New Jersey, New York, and California. The base pay for all other locations is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Clinical & Disease Specific Plan Strategy & Design

  • Own the full end to end lifecycle of clinical and disease specific insurance products from ideation/strategy and benefit design through launch, performance management, and optimization aligned to outcomes, regulatory requirements, affordability and growth objectives

  • Build and manage business cases for new and existing products, including financial modeling, membership projections, and ongoing performance tracking against goals

  • Analyze product performance using financial and membership metrics to forecast results, identify risks and opportunities, and inform decision-making

  • Lead benefit design for disease-specific plans, including augmenting existing offerings, remediating underperforming designs, and introducing new benefit structures informed by clinical insight, utilization patterns, and product performance

  • Design and manage product portfolios aligned to defined clinical populations, such as members with chronic conditions, high cost, or high utilization profiles, or condition specific care needs

  • Contribute to annual planning, roadmap development, and prioritization for clinical and disease-specific products

  • Identify risks, gaps, and opportunities across benefit design, performance, affordability, and access, recommending corrective actions as needed

   

  Execution, Filings and Regulatory Alignment

  • Responsible for execution of clinical plan designs through internal approvals, filings and supporting documentation

  • Partner with regulatory and legal teams and incorporate federal and state regulatory guidance, clinical mandates and medical policy changes into plan designs and pricing inputs.

  • Ensure compliance with all applicable laws, regulations, and internal governance standards

   

  Cross Functional Leadership & Collaboration

  • Serve as the primary product directly responsible individual (DRI) for clinical plans, coordinating all necessary plan aspects  across Clinical, Actuarial, Network, Medical Affairs, Finance,  Legal and Compliance

   

  Performance & Optimization

  • Develop and maintain regular performance reporting and product look-backs, assessing financial, clinical, operational, and outcomes across disease-specific populations

  • Lead cross-functional execution for clinical product enhancements, pilots, and issue resolution

  • Compliance with all applicable laws and regulations

  • Other duties as assigned

  
  
  

Requirements:

• 6+ years of experience developing, managing, or supporting commercial insurance products, including clinical programs and disease-specific product offerings

• 5+ years of experience and Understanding of clinical policy, utilization management, quality programs and regulatory requirements (ACA, state mandates, CMS guidance, etc…)

• 3+ years multi-year experience with ACA, including individual market place and small group products

• 3+ years demonstrated ownership of end to end product lifecycle management

• 3+ years experience and proven ability to lead   cross-functionally in highly regulated, matrixed and sometimes vague environments

• 3+  years experience making Strong analytical and data-driven decisions with Ability to translate population-specific insights into product and benefit design decisions

• Travel up to 25% of the time

Bonus points:

• Bachelor’s degree in business, healthcare, public policy, analytics, or related field

• Experience developing or managing clinically differentiated health plans.

• Familiarity with medical policy development, clinical governance and provider models.

• Experience supporting regulatory filings and audits

• Experience developing or managing products for chronic conditions, high-utilizer populations, or disease-specific cohorts

• Experience with business intelligence tools, experience with SQL, Excel, or similar tools

• Experience incorporating clinical outcomes, quality measures, and care management programs into product design

• Background in population health, value-based care, or care delivery innovation a plus

Hi, we're Oscar. We're hiring a Senior Analyst, Individual and Family Plan Insurance Solutions to join our Insurance Product Development team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Senior Analyst, Individual and Family Plan Insurance Solutions, provides foundational analytical research and product level support across Oscar’s individual and family (IFP) and employer-subsidized product portfolios. This role focuses on data analysis, market and competitive research, and performance monitoring of our markets to inform product strategy, design decisions, and execution readiness across on-exchange and employer-subsidized (ICHRA) solutions.

This role operates horizontally across product lines and segments, serving as an insight engine for product teams and enabling data-driven decision making in a regulated, multi-market environment.

You will report into the Vice President, Insurance Product Innovation and Development

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role is: $83,628 - $109,761 per year in New Jersey, New York, and California. The base pay for all other locations is: $75,265 - $98,785 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

Market, Policy, and Competitive Research

• Play a key role in building, maintaining and identifying improvements to models that forecast membership growth and retention rates in support of strategic decisionsConduct market and competitive research across individual and employer-subsidized health insurance offerings
• Analyze competitor plan designs, benefit structures, pricing approaches, and positioning
• Track regulatory and policy developments and support impact assessments for product teams
• Support population and employer-segment research initiatives

Product Performance Analytics

• Analyze product performance across growth, retention, utilization, and margin metrics
• Build and maintain recurring dashboards and performance reports
• Support deep-dive analyses for product reviews, remediation efforts, and future-year planning
• Identify trends, anomalies, and emerging risks through data analysis

Product & Filing Support

• Support product teams during filing cycles through data validation, QA, and analytical support
• Assist in preparation of analytical material required for regulatory submissions and internal reviews
• Ensure data accuracy and consistency across product artifacts

Insight Translation & Communication

• Translate complex analyses into clear, structured insights for product and cross-functional partners
• Prepare summaries, exhibits, and briefing materials for product leadership
• Support documentation of learnings to inform future product cycles
• Compliance with all applicable laws and regulationsOther duties as assigned
  
  

Requirements:

• 1+ years developing and managing commercial insurance products.
  
  
• Travel up to 25% of the time

Bonus points:

• BS/BA degree in a quantitative or healthcare field such as Business, Healthcare, Economics, Mathematics, Statistics, Actuarial Science and Finance or equivalent years of experience.
• 1+ years in a fast-paced, cross-functional environment such as consulting, finance, economics, or business development
• Proven analytical experience with the analytical skills to translate hard data into insight and action
• Prior experience in Health Insurance (Individual and/or Small Employer) and/or Healthcare industry
• Demonstrated ability to navigate ambiguity to drive to outcomes, work with large datasets and distill analyses into actionable business insights with a structured and systematic thought process

Hi, we're Oscar. We're hiring a Senior Accountant, Statutory and Legal Entity Reporting to join our Finance Ops & Accounting.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Financial Reporting is responsible for execution of statutory legal entity reports. This includes the preparation of statutory financial exhibits and footnotes, analytics, audited financial statements and supplemental filings.

You will report into the Associate Director, Financial Reporting.

Work Location: This is a remote position, open to candidates who reside in: Boston, MA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $82,717 - $108,566 per year.You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Monthly, quarterly and annual financial reporting
  • Completing the monthly, quarterly, and annual statutory (and stand-alone legal entity) reporting processes, including analytics and related financial statement disclosures.
  • Executing work related to the statutory audit efforts.
• Work on process improvement opportunities.
• Work with Regulatory Relations and other teams across the Organization to respond timely to regulator inquiries.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• 3+ years of related experience on an accounting or reporting team.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience with US-based insurance companies.
• Certified Public Accountant licensure (CPA).
• Practical experience in statutory reporting.

Hi, we're Oscar. We're hiring a Senior Accountant, Statutory and Legal Entity Reporting to join our Finance Ops & Accounting.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Financial Reporting is responsible for execution of statutory legal entity reports. This includes the preparation of statutory financial exhibits and footnotes, analytics, audited financial statements and supplemental filings.

You will report into the Associate Director, Financial Reporting.

Work Location: This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $82,717 - $108,566 per year.You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Monthly, quarterly and annual financial reporting
  • Completing the monthly, quarterly, and annual statutory (and stand-alone legal entity) reporting processes, including analytics and related financial statement disclosures.
  • Executing work related to the statutory audit efforts.
• Work on process improvement opportunities.
• Work with Regulatory Relations and other teams across the Organization to respond timely to regulator inquiries.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• 3+ years of related experience on an accounting or reporting team.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience with US-based insurance companies.
• Certified Public Accountant licensure (CPA).
• Practical experience in statutory reporting.

Hi, we're Oscar. We're hiring a Senior Accountant, Statutory and Legal Entity Reporting to join our Finance Ops & Accounting.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Financial Reporting is responsible for execution of statutory legal entity reports. This includes the preparation of statutory financial exhibits and footnotes, analytics, audited financial statements and supplemental filings.

You will report into the Associate Director, Financial Reporting.

Work Location: This is a remote position, open to candidates who reside in: Atlanta, GA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $82,717 - $108,566 per year.You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Monthly, quarterly and annual financial reporting
  • Completing the monthly, quarterly, and annual statutory (and stand-alone legal entity) reporting processes, including analytics and related financial statement disclosures.
  • Executing work related to the statutory audit efforts.
• Work on process improvement opportunities.
• Work with Regulatory Relations and other teams across the Organization to respond timely to regulator inquiries.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• 3+ years of related experience on an accounting or reporting team.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience with US-based insurance companies.
• Certified Public Accountant licensure (CPA).
• Practical experience in statutory reporting.

Hi, we're Oscar. We're hiring a Senior Accountant, Statutory and Legal Entity Reporting to join our Finance Ops & Accounting.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Financial Reporting is responsible for execution of statutory legal entity reports. This includes the preparation of statutory financial exhibits and footnotes, analytics, audited financial statements and supplemental filings.

You will report into the Associate Director, Financial Reporting.

Work Location: This is a remote position, open to candidates who reside in: Dallas, TX. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $82,717 - $108,566 per year.You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Monthly, quarterly and annual financial reporting
  • Completing the monthly, quarterly, and annual statutory (and stand-alone legal entity) reporting processes, including analytics and related financial statement disclosures.
  • Executing work related to the statutory audit efforts.
• Work on process improvement opportunities.
• Work with Regulatory Relations and other teams across the Organization to respond timely to regulator inquiries.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• 3+ years of related experience on an accounting or reporting team.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience with US-based insurance companies.
• Certified Public Accountant licensure (CPA).
• Practical experience in statutory reporting.

Hi, we're Oscar. We're hiring a Senior Accountant, Statutory and Legal Entity Reporting to join our Finance Ops & Accounting.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Financial Reporting is responsible for execution of statutory legal entity reports. This includes the preparation of statutory financial exhibits and footnotes, analytics, audited financial statements and supplemental filings.

You will report into the Associate Director, Financial Reporting.

Work Location: This position is based in our Tempe, AZ office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $82,717 - $108,566 per year.You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Monthly, quarterly and annual financial reporting
  • Completing the monthly, quarterly, and annual statutory (and stand-alone legal entity) reporting processes, including analytics and related financial statement disclosures.
  • Executing work related to the statutory audit efforts.
• Work on process improvement opportunities.
• Work with Regulatory Relations and other teams across the Organization to respond timely to regulator inquiries.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• 3+ years of related experience on an accounting or reporting team.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience with US-based insurance companies.
• Certified Public Accountant licensure (CPA).
• Practical experience in statutory reporting.

Hi, we're Oscar. We're hiring a Senior Accountant, Statutory and Legal Entity Reporting to join our Finance Ops & Accounting.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Financial Reporting is responsible for execution of statutory legal entity reports. This includes the preparation of statutory financial exhibits and footnotes, analytics, audited financial statements and supplemental filings.

You will report into the Associate Director, Financial Reporting.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $91,908 - $120,629 per year.You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Monthly, quarterly and annual financial reporting
  • Completing the monthly, quarterly, and annual statutory (and stand-alone legal entity) reporting processes, including analytics and related financial statement disclosures.
  • Executing work related to the statutory audit efforts.
• Work on process improvement opportunities.
• Work with Regulatory Relations and other teams across the Organization to respond timely to regulator inquiries.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• 3+ years of related experience on an accounting or reporting team.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience with US-based insurance companies.
• Certified Public Accountant licensure (CPA).
• Practical experience in statutory reporting.

Hi, we're Oscar. We're hiring a Manager to join our Treasury organization.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Treasury Manager is an individual contributor responsible for managing Oscar Health's important treasury operations and daily liquidity. You will provide critical daily execution of cash management activities, optimizes cash usage across subsidiaries, and guides operational efficiencies in banking and treasury systems.

The Manager will be a critical partner to the Treasury organization, driving the execution of cash management strategies in a capital-intensive insurance environment. You have a deep, operational understanding of Treasury practices.

You will report into the Senior Director, Assistant Treasurer.

Work Location: This is a remote position, open to candidates who reside in: Boston, MA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $108,000 - $141,750 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Liquidity Management & Optimization: Recommend and monitor minimum cash balances required at subsidiaries, based on forecasts from the Capital Planning team, to ensure safety and liquidity while optimizing excess cash for investment. Guide the efficient use of cash across the Parent and Subsidiaries.
• Cash Flow Reporting & Forecasting: Responsible for updating actual cash flows for each subsidiary and synchronizing with the Capital Planning team to ensure forecasted outflows are current. Updated cash forecasts and variances to the broader finance team.
• Reconciliation and Performance Analysis: Reconcile actual cash balances reported from Accounting with Treasury forecasts to true-up balances. Describe actual versus forecast variances, and update Net Investment Income (NII) actuals related to cash and short-term holdings.
• Operational Oversight & Execution: Build all critical treasury operations and daily banking activities. This includes ensuring accurate daily funds settlement, bank account maintenance, processing signatory updates, and the administration of bank portal systems (e.g., CashPro, JPM Access, WF Vantage).
• Risk & Fee Analysis: Measure banking service fees paid to financial institutions. Analyze counterparty risk exposures related to cash and bank balances.
• Operational Efficiency & Projects: Assist with project management, process improvement programs (e.g., RFPs, accounts/services rationalization), and implementing technology to enhance cash management and reporting functions.
• Audit and Compliance Support: Provide comprehensive operational support for all internal and external audits, SOX compliance controls, and state regulatory examinations, ensuring all processes are documented.
• Banking Relations: Serve as an important operational interface with external banking partners to resolve daily issues, manage service levels, and support routine operational tasks.
• Record Management and Governance: Responsible for managing all official records and documentation for Treasury Operations (e.g., debt indentures, banking agreements, fee invoices) within the shared file structure. Manage the Treasury Calendar of Events to track critical due dates for reports, payments, compliance filings, and renewals.

Requirements:

• Experience: 5+ years of progressive, hands-on experience in Corporate Treasury, Cash Management, or Treasury Operations within the financial services or insurance industry.
• Functional Expertise: 3+ years directly managing corporate liquidity, daily cash positioning, and detailed cash flow reporting/forecasting processes.
• Operational Systems: Operational experience using major online bank portals (e.g., CashPro, JPM Access, WF Vantage) and managing daily fund movements and settlements.
• Communication & Theory: Strong communication and presentation skills with the ability to articulate financial concepts. Must understand core Treasury Operations and cash management principle
• Education: Bachelor's degree in Finance, Accounting, Economics, or a related quantitative field.

Bonus points:

• Prior experience in Treasury Operations within an insurance or healthcare company.
• MBA and/or CTP certification is preferred. 
• Experience with ERP systems (e.g., Workday) and investment accounting/reporting systems (e.g., Clearwater) for data extraction and analysis; proficiency with Google Suite (Sheets, Docs, Drive) for collaboration and record management is a plus.

Hi, we're Oscar. We're hiring a Manager to join our Treasury organization.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Treasury Manager is an individual contributor responsible for managing Oscar Health's important treasury operations and daily liquidity. You will provide critical daily execution of cash management activities, optimizes cash usage across subsidiaries, and guides operational efficiencies in banking and treasury systems.

The Manager will be a critical partner to the Treasury organization, driving the execution of cash management strategies in a capital-intensive insurance environment. You have a deep, operational understanding of Treasury practices.

You will report into the Senior Director, Assistant Treasurer.

Work Location: This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $108,000 - $141,750 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Liquidity Management & Optimization: Recommend and monitor minimum cash balances required at subsidiaries, based on forecasts from the Capital Planning team, to ensure safety and liquidity while optimizing excess cash for investment. Guide the efficient use of cash across the Parent and Subsidiaries.
• Cash Flow Reporting & Forecasting: Responsible for updating actual cash flows for each subsidiary and synchronizing with the Capital Planning team to ensure forecasted outflows are current. Updated cash forecasts and variances to the broader finance team.
• Reconciliation and Performance Analysis: Reconcile actual cash balances reported from Accounting with Treasury forecasts to true-up balances. Describe actual versus forecast variances, and update Net Investment Income (NII) actuals related to cash and short-term holdings.
• Operational Oversight & Execution: Build all critical treasury operations and daily banking activities. This includes ensuring accurate daily funds settlement, bank account maintenance, processing signatory updates, and the administration of bank portal systems (e.g., CashPro, JPM Access, WF Vantage).
• Risk & Fee Analysis: Measure banking service fees paid to financial institutions. Analyze counterparty risk exposures related to cash and bank balances.
• Operational Efficiency & Projects: Assist with project management, process improvement programs (e.g., RFPs, accounts/services rationalization), and implementing technology to enhance cash management and reporting functions.
• Audit and Compliance Support: Provide comprehensive operational support for all internal and external audits, SOX compliance controls, and state regulatory examinations, ensuring all processes are documented.
• Banking Relations: Serve as an important operational interface with external banking partners to resolve daily issues, manage service levels, and support routine operational tasks.
• Record Management and Governance: Responsible for managing all official records and documentation for Treasury Operations (e.g., debt indentures, banking agreements, fee invoices) within the shared file structure. Manage the Treasury Calendar of Events to track critical due dates for reports, payments, compliance filings, and renewals.

Requirements:

• Experience: 5+ years of progressive, hands-on experience in Corporate Treasury, Cash Management, or Treasury Operations within the financial services or insurance industry.
• Functional Expertise: 3+ years directly managing corporate liquidity, daily cash positioning, and detailed cash flow reporting/forecasting processes.
• Operational Systems: Operational experience using major online bank portals (e.g., CashPro, JPM Access, WF Vantage) and managing daily fund movements and settlements.
• Communication & Theory: Strong communication and presentation skills with the ability to articulate financial concepts. Must understand core Treasury Operations and cash management principle
• Education: Bachelor's degree in Finance, Accounting, Economics, or a related quantitative field.

Bonus points:

• Prior experience in Treasury Operations within an insurance or healthcare company.
• MBA and/or CTP certification is preferred. 
• Experience with ERP systems (e.g., Workday) and investment accounting/reporting systems (e.g., Clearwater) for data extraction and analysis; proficiency with Google Suite (Sheets, Docs, Drive) for collaboration and record management is a plus.

Hi, we're Oscar. We're hiring a Manager to join our Treasury organization.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Treasury Manager is an individual contributor responsible for managing Oscar Health's important treasury operations and daily liquidity. You will provide critical daily execution of cash management activities, optimizes cash usage across subsidiaries, and guides operational efficiencies in banking and treasury systems.

The Manager will be a critical partner to the Treasury organization, driving the execution of cash management strategies in a capital-intensive insurance environment. You have a deep, operational understanding of Treasury practices.

You will report into the Senior Director, Assistant Treasurer.

Work Location: This position is based in our Tempe, AZ office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $97,200 - $127,575 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Liquidity Management & Optimization: Recommend and monitor minimum cash balances required at subsidiaries, based on forecasts from the Capital Planning team, to ensure safety and liquidity while optimizing excess cash for investment. Guide the efficient use of cash across the Parent and Subsidiaries.
• Cash Flow Reporting & Forecasting: Responsible for updating actual cash flows for each subsidiary and synchronizing with the Capital Planning team to ensure forecasted outflows are current. Updated cash forecasts and variances to the broader finance team.
• Reconciliation and Performance Analysis: Reconcile actual cash balances reported from Accounting with Treasury forecasts to true-up balances. Describe actual versus forecast variances, and update Net Investment Income (NII) actuals related to cash and short-term holdings.
• Operational Oversight & Execution: Build all critical treasury operations and daily banking activities. This includes ensuring accurate daily funds settlement, bank account maintenance, processing signatory updates, and the administration of bank portal systems (e.g., CashPro, JPM Access, WF Vantage).
• Risk & Fee Analysis: Measure banking service fees paid to financial institutions. Analyze counterparty risk exposures related to cash and bank balances.
• Operational Efficiency & Projects: Assist with project management, process improvement programs (e.g., RFPs, accounts/services rationalization), and implementing technology to enhance cash management and reporting functions.
• Audit and Compliance Support: Provide comprehensive operational support for all internal and external audits, SOX compliance controls, and state regulatory examinations, ensuring all processes are documented.
• Banking Relations: Serve as an important operational interface with external banking partners to resolve daily issues, manage service levels, and support routine operational tasks.
• Record Management and Governance: Responsible for managing all official records and documentation for Treasury Operations (e.g., debt indentures, banking agreements, fee invoices) within the shared file structure. Manage the Treasury Calendar of Events to track critical due dates for reports, payments, compliance filings, and renewals.

Requirements:

• Experience: 5+ years of progressive, hands-on experience in Corporate Treasury, Cash Management, or Treasury Operations within the financial services or insurance industry.
• Functional Expertise: 3+ years directly managing corporate liquidity, daily cash positioning, and detailed cash flow reporting/forecasting processes.
• Operational Systems: Operational experience using major online bank portals (e.g., CashPro, JPM Access, WF Vantage) and managing daily fund movements and settlements.
• Communication & Theory: Strong communication and presentation skills with the ability to articulate financial concepts. Must understand core Treasury Operations and cash management principle
• Education: Bachelor's degree in Finance, Accounting, Economics, or a related quantitative field.

Bonus points:

• Prior experience in Treasury Operations within an insurance or healthcare company.
• MBA and/or CTP certification is preferred. 
• Experience with ERP systems (e.g., Workday) and investment accounting/reporting systems (e.g., Clearwater) for data extraction and analysis; proficiency with Google Suite (Sheets, Docs, Drive) for collaboration and record management is a plus.

Hi, we're Oscar. We're hiring a Manager to join our Treasury organization.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Treasury Manager is an individual contributor responsible for managing Oscar Health's important treasury operations and daily liquidity. You will provide critical daily execution of cash management activities, optimizes cash usage across subsidiaries, and guides operational efficiencies in banking and treasury systems.

The Manager will be a critical partner to the Treasury organization, driving the execution of cash management strategies in a capital-intensive insurance environment. You have a deep, operational understanding of Treasury practices.

You will report into the Senior Director, Assistant Treasurer.

Work Location: 

This is a remote position, open to candidates who reside in: Dallas, TX. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $97,200 - $127,575 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Liquidity Management & Optimization: Recommend and monitor minimum cash balances required at subsidiaries, based on forecasts from the Capital Planning team, to ensure safety and liquidity while optimizing excess cash for investment. Guide the efficient use of cash across the Parent and Subsidiaries.
• Cash Flow Reporting & Forecasting: Responsible for updating actual cash flows for each subsidiary and synchronizing with the Capital Planning team to ensure forecasted outflows are current. Updated cash forecasts and variances to the broader finance team.
• Reconciliation and Performance Analysis: Reconcile actual cash balances reported from Accounting with Treasury forecasts to true-up balances. Describe actual versus forecast variances, and update Net Investment Income (NII) actuals related to cash and short-term holdings.
• Operational Oversight & Execution: Build all critical treasury operations and daily banking activities. This includes ensuring accurate daily funds settlement, bank account maintenance, processing signatory updates, and the administration of bank portal systems (e.g., CashPro, JPM Access, WF Vantage).
• Risk & Fee Analysis: Measure banking service fees paid to financial institutions. Analyze counterparty risk exposures related to cash and bank balances.
• Operational Efficiency & Projects: Assist with project management, process improvement programs (e.g., RFPs, accounts/services rationalization), and implementing technology to enhance cash management and reporting functions.
• Audit and Compliance Support: Provide comprehensive operational support for all internal and external audits, SOX compliance controls, and state regulatory examinations, ensuring all processes are documented.
• Banking Relations: Serve as an important operational interface with external banking partners to resolve daily issues, manage service levels, and support routine operational tasks.
• Record Management and Governance: Responsible for managing all official records and documentation for Treasury Operations (e.g., debt indentures, banking agreements, fee invoices) within the shared file structure. Manage the Treasury Calendar of Events to track critical due dates for reports, payments, compliance filings, and renewals.

Requirements:

• Experience: 5+ years of progressive, hands-on experience in Corporate Treasury, Cash Management, or Treasury Operations within the financial services or insurance industry.
• Functional Expertise: 3+ years directly managing corporate liquidity, daily cash positioning, and detailed cash flow reporting/forecasting processes.
• Operational Systems: Operational experience using major online bank portals (e.g., CashPro, JPM Access, WF Vantage) and managing daily fund movements and settlements.
• Communication & Theory: Strong communication and presentation skills with the ability to articulate financial concepts. Must understand core Treasury Operations and cash management principle
• Education: Bachelor's degree in Finance, Accounting, Economics, or a related quantitative field.

Bonus points:

• Prior experience in Treasury Operations within an insurance or healthcare company.
• MBA and/or CTP certification is preferred. 
• Experience with ERP systems (e.g., Workday) and investment accounting/reporting systems (e.g., Clearwater) for data extraction and analysis; proficiency with Google Suite (Sheets, Docs, Drive) for collaboration and record management is a plus.

Hi, we're Oscar. We're hiring a Manager to join our Treasury organization.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Treasury Manager is an individual contributor responsible for managing Oscar Health's important treasury operations and daily liquidity. You will provide critical daily execution of cash management activities, optimizes cash usage across subsidiaries, and guides operational efficiencies in banking and treasury systems.

The Manager will be a critical partner to the Treasury organization, driving the execution of cash management strategies in a capital-intensive insurance environment. You have a deep, operational understanding of Treasury practices.

You will report into the Senior Director, Assistant Treasurer.

Work Location: 

This is a remote position, open to candidates who reside in: Atlanta, GA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $97,200 - $127,575 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Liquidity Management & Optimization: Recommend and monitor minimum cash balances required at subsidiaries, based on forecasts from the Capital Planning team, to ensure safety and liquidity while optimizing excess cash for investment. Guide the efficient use of cash across the Parent and Subsidiaries.
• Cash Flow Reporting & Forecasting: Responsible for updating actual cash flows for each subsidiary and synchronizing with the Capital Planning team to ensure forecasted outflows are current. Updated cash forecasts and variances to the broader finance team.
• Reconciliation and Performance Analysis: Reconcile actual cash balances reported from Accounting with Treasury forecasts to true-up balances. Describe actual versus forecast variances, and update Net Investment Income (NII) actuals related to cash and short-term holdings.
• Operational Oversight & Execution: Build all critical treasury operations and daily banking activities. This includes ensuring accurate daily funds settlement, bank account maintenance, processing signatory updates, and the administration of bank portal systems (e.g., CashPro, JPM Access, WF Vantage).
• Risk & Fee Analysis: Measure banking service fees paid to financial institutions. Analyze counterparty risk exposures related to cash and bank balances.
• Operational Efficiency & Projects: Assist with project management, process improvement programs (e.g., RFPs, accounts/services rationalization), and implementing technology to enhance cash management and reporting functions.
• Audit and Compliance Support: Provide comprehensive operational support for all internal and external audits, SOX compliance controls, and state regulatory examinations, ensuring all processes are documented.
• Banking Relations: Serve as an important operational interface with external banking partners to resolve daily issues, manage service levels, and support routine operational tasks.
• Record Management and Governance: Responsible for managing all official records and documentation for Treasury Operations (e.g., debt indentures, banking agreements, fee invoices) within the shared file structure. Manage the Treasury Calendar of Events to track critical due dates for reports, payments, compliance filings, and renewals.

Requirements:

• Experience: 5+ years of progressive, hands-on experience in Corporate Treasury, Cash Management, or Treasury Operations within the financial services or insurance industry.
• Functional Expertise: 3+ years directly managing corporate liquidity, daily cash positioning, and detailed cash flow reporting/forecasting processes.
• Operational Systems: Operational experience using major online bank portals (e.g., CashPro, JPM Access, WF Vantage) and managing daily fund movements and settlements.
• Communication & Theory: Strong communication and presentation skills with the ability to articulate financial concepts. Must understand core Treasury Operations and cash management principle
• Education: Bachelor's degree in Finance, Accounting, Economics, or a related quantitative field.

Bonus points:

• Prior experience in Treasury Operations within an insurance or healthcare company.
• MBA and/or CTP certification is preferred. 
• Experience with ERP systems (e.g., Workday) and investment accounting/reporting systems (e.g., Clearwater) for data extraction and analysis; proficiency with Google Suite (Sheets, Docs, Drive) for collaboration and record management is a plus.

Hi, we're Oscar. We're hiring a Manager to join our Treasury organization.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Treasury Manager is an individual contributor responsible for managing Oscar Health's important treasury operations and daily liquidity. You will provide critical daily execution of cash management activities, optimizes cash usage across subsidiaries, and guides operational efficiencies in banking and treasury systems.

The Manager will be a critical partner to the Treasury organization, driving the execution of cash management strategies in a capital-intensive insurance environment. You have a deep, operational understanding of Treasury practices.

You will report into the Senior Director, Assistant Treasurer.

Work Location: This position is based in our NYC office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $108,000 - $141,750 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Liquidity Management & Optimization: Recommend and monitor minimum cash balances required at subsidiaries, based on forecasts from the Capital Planning team, to ensure safety and liquidity while optimizing excess cash for investment. Guide the efficient use of cash across the Parent and Subsidiaries.
• Cash Flow Reporting & Forecasting: Responsible for updating actual cash flows for each subsidiary and synchronizing with the Capital Planning team to ensure forecasted outflows are current. Updated cash forecasts and variances to the broader finance team.
• Reconciliation and Performance Analysis: Reconcile actual cash balances reported from Accounting with Treasury forecasts to true-up balances. Describe actual versus forecast variances, and update Net Investment Income (NII) actuals related to cash and short-term holdings.
• Operational Oversight & Execution: Build all critical treasury operations and daily banking activities. This includes ensuring accurate daily funds settlement, bank account maintenance, processing signatory updates, and the administration of bank portal systems (e.g., CashPro, JPM Access, WF Vantage).
• Risk & Fee Analysis: Measure banking service fees paid to financial institutions. Analyze counterparty risk exposures related to cash and bank balances.
• Operational Efficiency & Projects: Assist with project management, process improvement programs (e.g., RFPs, accounts/services rationalization), and implementing technology to enhance cash management and reporting functions.
• Audit and Compliance Support: Provide comprehensive operational support for all internal and external audits, SOX compliance controls, and state regulatory examinations, ensuring all processes are documented.
• Banking Relations: Serve as an important operational interface with external banking partners to resolve daily issues, manage service levels, and support routine operational tasks.
• Record Management and Governance: Responsible for managing all official records and documentation for Treasury Operations (e.g., debt indentures, banking agreements, fee invoices) within the shared file structure. Manage the Treasury Calendar of Events to track critical due dates for reports, payments, compliance filings, and renewals.

Requirements:

• Experience: 5+ years of progressive, hands-on experience in Corporate Treasury, Cash Management, or Treasury Operations within the financial services or insurance industry.
• Functional Expertise: 3+ years directly managing corporate liquidity, daily cash positioning, and detailed cash flow reporting/forecasting processes.
• Operational Systems: Operational experience using major online bank portals (e.g., CashPro, JPM Access, WF Vantage) and managing daily fund movements and settlements.
• Communication & Theory: Strong communication and presentation skills with the ability to articulate financial concepts. Must understand core Treasury Operations and cash management principle
• Education: Bachelor's degree in Finance, Accounting, Economics, or a related quantitative field.

Bonus points:

• Prior experience in Treasury Operations within an insurance or healthcare company.
• MBA and/or CTP certification is preferred. 
• Experience with ERP systems (e.g., Workday) and investment accounting/reporting systems (e.g., Clearwater) for data extraction and analysis; proficiency with Google Suite (Sheets, Docs, Drive) for collaboration and record management is a plus.

Hi, we're Oscar. We're hiring a Director, Speciality, Multicultural, and Innovative Insurance Product Solutions to join our Insurance Product Development team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Director, Speciality, Multicultural, and Innovative Insurance Product Solutions is accountable for the end to end strategy, design, execution and performance of a portfolio of differentiated product solutions that address complex, high need and emerging member segments designed to serve diverse populations and specialized consumer needs. This role owns innovation initiatives across multicultural plans, affordability-focused offerings, clinical plan design, and ancillary benefits, ensuring products are competitive, compliant, and operationally scalable.

You will report into the Vice President, Insurance Product Innovation and Development

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role is: $180,504 - $236,911 per year in New Jersey, New York, and California. The base pay for all other locations is: $162,453 - $213,220 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Own the portfolio strategy, design, continuous improvement and long term vision for specialty, multicultural and innovative product solutions, including Determining and being accountable for which speciality and multicultural products are launched, expanded, modified, or discontinued based on performance, consumer insights, and market dynamics

• Identify opportunities driven by member needs, health disparities, utilization trends, cost drivers and market dynamics

• Define product intents, investment and roadmaps aligned to enterprise growth, equity, quality and affordability goals

• Serve as a thought leader to drive ideation and development of clinically informed plan designed aligned to specific populations, conditions, and community needs for differentiated and emerging product solutions

• Own innovation initiatives focused on affordability, access, and clinical differentiation, including benefit design, cost-sharing strategies, and targeted plan constructs

• Own financial and membership performance tracking for products, projecting outcomes, measuring success against targets, and adjusting strategy based on data-driven insights

• Oversee development and integration of ancillary benefits and products, ensuring alignment with core medical offerings and regulatory requirements

• Drive standardization where possible while allowing for market-specific customization

• Set quality standards for documentation, requirements and approvals

• Establish an analytics-driven operating model across the product portfolio in collaboration with the analytics team, developing segmentation frameworks, dashboards and KPIs (e.g. access, utilization, quality, engagement, cost and experience) and translate complex analyses into clear executive-level insights and recommendations

• Responsible for execution of multicultural, innovative, speciality, and clinical plan designs through internal approvals, filings and supporting documentation

Cross Functional Leadership & Regulatory Partnership

• Partner with cross functional teams including Actuarial, Clinical, Network, Regulatory, and legal to align benefit design, pricing, provider strategies, affordability objectives, and compliance with federal and state requirements

• Lead cross-functional teams through product development, regulatory filing, implementation readiness, and post-launch performance evaluation

• Build, lead, and develop high-performing product teams, setting clear expectations, priorities, and accountability

• Foster an inclusive, safe team culture that values diverse perspectives and encourages thoughtful risk-taking and innovation

Requirements:

• Bachelors Degree or 4+ commensurate work experience

• 10+ years of experience developing and managing commercial insurance products

• 8+ years experience with people leadership, including managing managers or senior individual contributors

• 6+ years of experience developing, evaluating, and monitoring business cases, including revenue forecasts, cost structures, ROI, and long-term value creation

• Travel up to 25% of the time

Bonus points:

• Bachelor’s degree or higher in business, healthcare or quantitative degree

• Experience developing products for diverse, multicultural, or underserved populations

• Experience with affordability initiatives, clinically oriented plan designs, or specialized ancillary benefit structures

• Familiarity with ancillary products (e.g., dental, vision, supplemental health benefits)

• Track record of developing leaders and shaping strong team culture

• Experience with the Qualified Health Plan certification process

Hi, we're Oscar. We're hiring an Associate, Solutions Execution to join our Insurance Product Development team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Solutions Execution plays a critical role with the Product organization with a primary focus on product filings, plan benefit templates (PBT’s) and program governance.. This role is responsible for supporting QA documentation, production and publication readiness, version control and exact execution to ensure the product changes are delivered accurately, on time and in accordance with established controls and calendars. This role serves as an operational hub for Product Managers and support teams, ensuring documentation is complete, clean, and consistently maintained, while helping enforce freeze periods, distribution protocols and third party coordination.

You will report into the Vice President, Insurance Product Innovation and Development

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role is: $101,844 - $133,670 per year in New Jersey, New York, and California. The base pay for all other locations is: $91,659 - $120,303 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Support preparation, maintenance, and submission of insurance product filing materials, including PBT’s, SBC’s, and SOB’s

• Ensure benefit designs, cost sharing, and product configurations are accurately reflected across filing documentation, with little to no rework

• Support the documentation of  quality assurance activities to ensure filing accuracy and compliance

• Ensure compliance with applicable laws, regulations, and internal governance standards

• Support production extract execution in alignment with the established calendar and production schedule

• Ensure extracts are pulled accurately and distributed to downstream partners as required

• Assist in monitoring and enforcing system freeze windows to prevent unauthorized changes during critical periods

• Support version control and distribution processes, ensuring artifacts are properly labeled, stored and distributed

• Orchestrate cross-functional initiatives by structuring project plans, monitoring projects, managing issue resolution, and ensuring alignment across senior stakeholders

• Track updates, changes, and version control across filing cycles, including regulatory objections

• Support governance processes and tracking of filing timelines by documenting decisions, approvals, key milestones

• Coordinate inputs and outputs across Product, Regulatory, Operations, Implementation, and Legal teams

• Assist with regulator follow-ups and filing related inquiries and Identify risks, inconsistencies, or gaps and escalate as appropriate

• Support the multi-year product operating model including integration of market research, competitive analysis, product positioning, and product performance

• Provide administrative coordination support for insurance product strategy, innovation and execution teams, as well as third party vendors supporting product execution or QA activities

• Compliance with all applicable laws and regulations

• Other duties as assigned

Requirements:

• 3+ years of experience supporting insurance products, regulatory filings, and related program management work

• 2+ years of experience with ACA, individual, or small group insurance products, including filing programs

• 2 + years of experience with regulatory filing QA and version control

• 1+ years of experience working in a cross-functional, fast-paced environment

• 1+ years of experience working with calendars, deadlines and production schedules

• 1+ years of experience working across multiple teams and managing competing priorities

• 1+ years of experience with documentation tools, spreadsheets and collaboration platforms

• Travel up to 25% of the time

Bonus points:

• Bachelor’s degree in business, healthcare, public policy, or related field

• Familiarity with PBT’s, SOB’s, and SBC’s, including other regulatory filings and insurance product documentation

• Strong organizational, communication, and follow-through skills

• Proficiency with Google Suite and Microsoft Suite products, including familiarity with data tools and filing systems

• Proficiency with Excel and SQL required to manipulate and analyze data, (R, and/or Python beneficial)

• Demonstrated ability to navigate ambiguity to drive to outcomes, work with large datasets and distill analyses into actionable business insights

Hi, we're Oscar. We're hiring an Associate, Individual and Family Plan Insurance Solutions to join our Insurance Product Development team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Individual and Family Plan Insurance Solutions, supports end to end product strategy, research, and delivery across Oscar’s Individual & Family (IFP) and employer-subsidized (e.g., ICHRA) solutions. This role operates horizontally across product lines, partnering with product management, market leadership, actuarial, regulatory, operations, and analytics to support product design decisions, filing readiness, and in-market performance through structured research, analysis, and disciplined execution.

You will report into the Vice President, Insurance Product Innovation and Development

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role is: $106,812 - $140,190 per year in New Jersey, New York, and California. The base pay for all other locations is: $96,130 - $126,171 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Product Strategy & Research

  • Identify and provide key data and market insights that contribute to the design, launch and management of a product portfolio based on current product performance, competitive market, and new industry trends

  • For a subset of the portfolio, play a key role in determining which products should be added, modified, or discontinued based on product performance results

  • Support product strategy development across on-exchange and employer-subsidized offerings through market research, competitive analysis, and internal performance insights

  • Conduct structured qualitative and quantitative research to inform product design decisions, including benefit structures, cost-sharing approaches, and positioning

  • Track and synthesize regulatory, policy, and market developments and assess potential product impacts

  • Support population and segment based research to understand member and employer needs across portfolios

   

  Cross Functional Execution Support

  • Support execution of product initiatives that span IFP and employer-subsidized solutions

  • Assist in development of product artifacts required for filings, launch readiness, and internal governance

  • Coordinate inputs across product, market, actuarial, regulatory, and operational teams to ensure alignment and completeness

  • Track timelines, dependencies, and risks across multiple concurrent workstreams

   

  Performance Monitoring & Insight Development

  • Support monitoring of post-launch product performance across growth, retention, utilization, and margin metrics

  • Develop analyses to identify emerging risks, performance gaps, and optimization opportunities

  • Prepare materials to support post-launch reviews, remediation discussions, and future year planning

   

  Governance, Quality & Documentation

  • Support QA and validation of product designs, filing materials, and supporting documentation

  • Assist in documenting assumptions, decision, and learnings to support auditability and future cycles

  • Compliance with all applicable laws and regulations

  • Other duties as assigned

Requirements:

• 3+ years experience developing and managing commercial insurance products.

• Travel up to 25% of the time

Bonus points:

• BS/BA degree in a quantitative or healthcare field such as Business, Healthcare, Economics, Mathematics, Statistics, Actuarial Science and Finance or equivalent years of experience.

• 3+ years in a fast-paced, cross-functional environment such as consulting, finance, economics, or business development

• Proven analytical experience with the analytical skills to translate hard data into insight and action

• Prior experience in Health Insurance (Individual and/or Small Employer) and/or Healthcare industry

• Demonstrated ability to navigate ambiguity to drive to outcomes, work with large datasets and distill analyses into actionable business insights with a structured and systematic thought process

Hi, we're Oscar. We're hiring an Associate Director, Tax to join our Finance.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate Director, Tax leads income tax compliance including tax provisions under Generally Accepted Accounting principles (GAAP) and Statutory reporting, federal, state and local tax returns, and tax planning and projects. The Associate Director, Tax supports the Tax leadership team in developing department strategy.

You will report into the Sr. Director, Tax.

Work Location: This position is based in our Tempe, AZ office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $162,453 - $213,220 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Manage the annual and quarterly tax GAAP and Statutory tax provision processes and lead the related internal and external relationships necessary to support these processes.
• Review U.S. federal, state, and local tax returns and estimates for the corporate holding companies and insurance subsidiaries and manage our relationship with external consultants on this work.
• Ensure integrity of tax accounting and compliance results using technology solutions, partnering with the Finance Transformation Team and the Company's external vendors.
• Manage tax responses to audits and notices and the related correspondence with internal and external parties.
• Ensure compliance with indirect tax compliance functions.
• Lead the preparation of financial data and analysis to support tax forecasting and projects.
• Partner with areas of Finance and the business to address tax issues and meet organizational goals.
• Stay abreast and educate others on developments within the insurance tax area and their possible effects to the Company.
• Help develop and implement tax strategies and planning opportunities.
• Automate processes to refine tax compliance and provide analytical insights.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• Bachelor's degree in Accounting, or 4 years commensurate experience.
• 7+ years of tax experience in a public accounting firm or equivalent experience in a corporate tax department.
• Proficient in using code and regulations.
• Strong knowledge in ASC 740.
• 3+ years experience as a team leader.

Bonus points:

• CPA and/or Master's of Taxation.
• Statement of Statutory Accounting Principle (SSAP) 101 reporting.
• Knowledge of domestic tax issues affecting U.S. insurance companies.
• Experience implementing tax provision software.
• Work with large datasets to build models and leverage tools.
• Experience with state tax nexus considerations.

Hi, we're Oscar. We're hiring an Associate Director, Tax to join our Finance.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate Director, Tax leads income tax compliance including tax provisions under Generally Accepted Accounting principles (GAAP) and Statutory reporting, federal, state and local tax returns, and tax planning and projects. The Associate Director, Tax supports the Tax leadership team in developing department strategy.

You will report into the Sr. Director, Tax.

Work Location: 

This is a remote position, open to candidates who reside in: Atlanta, GA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $162,453 - $213,220 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Manage the annual and quarterly tax GAAP and Statutory tax provision processes and lead the related internal and external relationships necessary to support these processes.
• Review U.S. federal, state, and local tax returns and estimates for the corporate holding companies and insurance subsidiaries and manage our relationship with external consultants on this work.
• Ensure integrity of tax accounting and compliance results using technology solutions, partnering with the Finance Transformation Team and the Company's external vendors.
• Manage tax responses to audits and notices and the related correspondence with internal and external parties.
• Ensure compliance with indirect tax compliance functions.
• Lead the preparation of financial data and analysis to support tax forecasting and projects.
• Partner with areas of Finance and the business to address tax issues and meet organizational goals.
• Stay abreast and educate others on developments within the insurance tax area and their possible effects to the Company.
• Help develop and implement tax strategies and planning opportunities.
• Automate processes to refine tax compliance and provide analytical insights.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• Bachelor's degree in Accounting, or 4 years commensurate experience.
• 7+ years of tax experience in a public accounting firm or equivalent experience in a corporate tax department.
• Proficient in using code and regulations.
• Strong knowledge in ASC 740.
• 3+ years experience as a team leader.

Bonus points:

• CPA and/or Master's of Taxation.
• Statement of Statutory Accounting Principle (SSAP) 101 reporting.
• Knowledge of domestic tax issues affecting U.S. insurance companies.
• Experience implementing tax provision software.
• Work with large datasets to build models and leverage tools.
• Experience with state tax nexus considerations.

Hi, we're Oscar. We're hiring an Associate Director, Tax to join our Finance.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate Director, Tax leads income tax compliance including tax provisions under Generally Accepted Accounting principles (GAAP) and Statutory reporting, federal, state and local tax returns, and tax planning and projects. The Associate Director, Tax supports the Tax leadership team in developing department strategy.

You will report into the Sr. Director, Tax.

Work Location: 

This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $180,504 - $236,911 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Manage the annual and quarterly tax GAAP and Statutory tax provision processes and lead the related internal and external relationships necessary to support these processes.
• Review U.S. federal, state, and local tax returns and estimates for the corporate holding companies and insurance subsidiaries and manage our relationship with external consultants on this work.
• Ensure integrity of tax accounting and compliance results using technology solutions, partnering with the Finance Transformation Team and the Company's external vendors.
• Manage tax responses to audits and notices and the related correspondence with internal and external parties.
• Ensure compliance with indirect tax compliance functions.
• Lead the preparation of financial data and analysis to support tax forecasting and projects.
• Partner with areas of Finance and the business to address tax issues and meet organizational goals.
• Stay abreast and educate others on developments within the insurance tax area and their possible effects to the Company.
• Help develop and implement tax strategies and planning opportunities.
• Automate processes to refine tax compliance and provide analytical insights.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• Bachelor's degree in Accounting, or 4 years commensurate experience.
• 7+ years of tax experience in a public accounting firm or equivalent experience in a corporate tax department.
• Proficient in using code and regulations.
• Strong knowledge in ASC 740.
• 3+ years experience as a team leader.

Bonus points:

• CPA and/or Master's of Taxation.
• Statement of Statutory Accounting Principle (SSAP) 101 reporting.
• Knowledge of domestic tax issues affecting U.S. insurance companies.
• Experience implementing tax provision software.
• Work with large datasets to build models and leverage tools.
• Experience with state tax nexus considerations.

Hi, we're Oscar. We're hiring an Associate Director, Tax to join our Finance.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate Director, Tax leads income tax compliance including tax provisions under Generally Accepted Accounting principles (GAAP) and Statutory reporting, federal, state and local tax returns, and tax planning and projects. The Associate Director, Tax supports the Tax leadership team in developing department strategy.

You will report into the Sr. Director, Tax.

Work Location: 

This is a remote position, open to candidates who reside in: Dallas, TX. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $162,453 - $213,220 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Manage the annual and quarterly tax GAAP and Statutory tax provision processes and lead the related internal and external relationships necessary to support these processes.
• Review U.S. federal, state, and local tax returns and estimates for the corporate holding companies and insurance subsidiaries and manage our relationship with external consultants on this work.
• Ensure integrity of tax accounting and compliance results using technology solutions, partnering with the Finance Transformation Team and the Company's external vendors.
• Manage tax responses to audits and notices and the related correspondence with internal and external parties.
• Ensure compliance with indirect tax compliance functions.
• Lead the preparation of financial data and analysis to support tax forecasting and projects.
• Partner with areas of Finance and the business to address tax issues and meet organizational goals.
• Stay abreast and educate others on developments within the insurance tax area and their possible effects to the Company.
• Help develop and implement tax strategies and planning opportunities.
• Automate processes to refine tax compliance and provide analytical insights.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• Bachelor's degree in Accounting, or 4 years commensurate experience.
• 7+ years of tax experience in a public accounting firm or equivalent experience in a corporate tax department.
• Proficient in using code and regulations.
• Strong knowledge in ASC 740.
• 3+ years experience as a team leader.

Bonus points:

• CPA and/or Master's of Taxation.
• Statement of Statutory Accounting Principle (SSAP) 101 reporting.
• Knowledge of domestic tax issues affecting U.S. insurance companies.
• Experience implementing tax provision software.
• Work with large datasets to build models and leverage tools.
• Experience with state tax nexus considerations.