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 Staff Product Manager to join our AI 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 Staff Product Manager is a senior individual contributor role responsible for defining and driving complex, technical product initiatives with strategic impact across the organization. In this role, you will identify and solve the most valuable business problems through deep user empathy, sharp product intuition, and a strong understanding of Oscar’s operating model and business levers. You will partner closely with engineering, data, and design to lead complex initiatives across domains, aligning directly with senior business leaders on priorities and outcomes. You will act as a force multiplier within the organization—mentoring peers, influencing product practices, and consistently raising the bar on quality, clarity, and impact.

In this Staff Product Manager role, you will focus on AI research and development. You’ll work closely with a small team of engineers and data scientists to explore and prototype new concepts and workflows across Oscar.

You will report into the Senior Director, AI.

Work Location:

This is a remote position, open to candidates who reside in: San Francisco, CA. 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: $180,504.00 - $236,911.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Helping to define the vision, strategy and roadmap for tech components, workflows, and insights that make it easy for teams across Oscar to leverage AI.
• Partnering closely with stakeholders including cross functional department leaders across the business to define strategy and roadmap.
• Collaborating with Engineering and Product leadership to make resource trade-off decisions and to ensure teams are working together effectively.
• Provide recommendations to leadership for product enhancements to improve existing products and development of new ones. 
• Develop operating models for new products in partnership with leadership.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• 7+ years of Product Management experience. 
• 1+ years of Product Management experience in an AI or healthcare setting. 
• Experience building a net new product 0-1. 

Bonus points

• Experience developing AI or ML-related features strongly preferred.
• Experience building AI infrastructure. 
• SQL skills strongly preferred.
• Comfort in working in highly collaborative environments while ensuring the team is always driving towards a decision.
• Excellent analytical and quantitative skills; proved experience using data to identify opportunities, test theories and evaluate success.
• Experience as an end-to-end thinker; the ability to look at a problem and create a solution all the way from top-level goals to smaller details.
• Ability to influence and manage stakeholders at all levels and experience working across all levels of leadership using strong communication and structured thinking.

Hi, we're Oscar. We're hiring Staff Product Managers to join our Product 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

The Staff Product Manager is a senior individual contributor role responsible for defining and driving complex, technical product initiatives with strategic impact across the organization. In this role, you will identify and solve the most valuable business problems through deep user empathy, sharp product intuition, and a strong understanding of Oscar’s operating model and business levers. You will partner closely with engineering, data, and design to lead complex initiatives across domains, aligning directly with senior business leaders on priorities and outcomes. You will act as a force multiplier within the product organization—mentoring peers, influencing product practices, and consistently raising the bar on quality, clarity, and impact. 

We are currently hiring for Staff Product Managers across our Network and Claims pillars. By applying to this job advertisement, you will be considered for both opportunities. 

You will report to the Sr. Director, Product Management.

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: $180,504.00 - $236,911.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities

• Driving the execution of complex, cross-functional initiatives by managing projects that will drive operational efficiencies and achieve key business objectives.
• Partnering closely with stakeholders including cross functional department leaders across the business including Product, Design, Engineering, Network and Claims Operations to define strategy and roadmap.
• Collaborating with Engineering and Product leadership to make resource trade-off decisions and to ensure teams are working together effectively.
• Provide recommendations to leadership for product enhancements to improve existing products and development of new ones. 
• Develop operating models for new products in partnership with leadership.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Qualifications

• 7+ years of product management experience. 

Bonus Points

• Comfort in working in highly collaborative environments while ensuring the team is always driving towards a decision.
• Excellent analytical and quantitative skills; proved experience using data to identify opportunities, test theories and evaluate success.
• Experience as an end-to-end thinker; the ability to look at a problem and create a solution all the way from top-level goals to smaller details.
• Ability to influence and manage stakeholders at all levels and experience working across all levels of leadership using strong communication and structured thinking.

Hi, we're Oscar. We're hiring a Staff Product Manager to join our AI 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 Staff Product Manager is a senior individual contributor role responsible for defining and driving complex, technical product initiatives with strategic impact across the organization. In this role, you will identify and solve the most valuable business problems through deep user empathy, sharp product intuition, and a strong understanding of Oscar’s operating model and business levers. You will partner closely with engineering, data, and design to lead complex initiatives across domains, aligning directly with senior business leaders on priorities and outcomes. You will act as a force multiplier within the organization—mentoring peers, influencing product practices, and consistently raising the bar on quality, clarity, and impact.

In this Staff Product Manager role, you will focus on AI research and development. You’ll work closely with a small team of engineers and data scientists to explore and prototype new concepts and workflows across Oscar.

You will report into the Senior Director, AI.

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: $180,504.00 - $236,911.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Helping to define the vision, strategy and roadmap for tech components, workflows, and insights that make it easy for teams across Oscar to leverage AI.
• Partnering closely with stakeholders including cross functional department leaders across the business to define strategy and roadmap.
• Collaborating with Engineering and Product leadership to make resource trade-off decisions and to ensure teams are working together effectively.
• Provide recommendations to leadership for product enhancements to improve existing products and development of new ones. 
• Develop operating models for new products in partnership with leadership.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• 7+ years of Product Management experience. 
• 1+ years of Product Management experience in an AI or healthcare setting. 
• Experience building a net new product 0-1. 

Bonus points

• Experience developing AI or ML-related features strongly preferred.
• Experience building AI infrastructure. 
• SQL skills strongly preferred.
• Comfort in working in highly collaborative environments while ensuring the team is always driving towards a decision.
• Excellent analytical and quantitative skills; proved experience using data to identify opportunities, test theories and evaluate success.
• Experience as an end-to-end thinker; the ability to look at a problem and create a solution all the way from top-level goals to smaller details.
• Ability to influence and manage stakeholders at all levels and experience working across all levels of leadership using strong communication and structured thinking.

Hi, we're Oscar. We're hiring a Director, Product Design to join our Product Design 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 strategic Product Design Director to lead a team of designers supporting our internal tools and enterprise ecosystem. In this role, you will oversee the designers building mission-critical platforms that power our business operations. Your mission is to ensure our internal users receive the same high-quality, user-centric experiences as our external customers. As Director, you will uphold a rigorous quality bar, ensuring our tools are not only functional but empower employees to deliver exceptional value to the business and our end-users.

You will report into the Sr. Director, Product Design.

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: $198,720.00 - $260,820.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Partner with Product and Engineering leads to define area strategy, roadmaps, set measurable goals, and ensure the timely and efficient delivery of high-impact solutions.
• Connect the dots across multiple domains: Network Management, Provider Tooling, and Clinical Experiences, to ensure cohesive, end-to-end ecosystems.
• Propose and lead design-driven initiatives, facilitating discovery and framing long-term strategic opportunities that align with business goals.
• Lead and develop a high-performing team of seasoned designers, fostering a culture of continuous growth and creative excellence.
• Own team resourcing, performance management, and prioritization, optimizing workflows to ensure the team is focused on the highest-leverage work.
• Effectively represent the product design org in executive forums, articulating the rationale behind design directions and highlighting the impact on the business.
• Maintain an uncompromising standard for design execution and craft through direct feedback, design reviews, and hands-on guidance.
• Manage stakeholder relationships, driving towards clarity around decision making and influencing direction through informed insights   
• Focus on scalability by implementing repeatable design processes and contributing to the evolution of a unified design language across multiple domains.
• Contribute to the future of the Product Design and Research function by optimizing our internal workflows, refining our engagement models, and ensuring the team has access to the best-in-class tooling and resources to do great work.  
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Requirements:

• 10+ years of experience in product design, building and shipping applications or software across various experiences.
• 5+ years of experience in a design leadership role, directly contributing and leading people, process, and product strategies.
• Ability to solve difficult problems through past work experience and case studies with evidence of design contributions across power-user interfaces.
• Experience shaping design direction and strategic thinking, identifying goals and opportunities, and making impact-based decisions.
• Engaging presentation skills and the ability to tell compelling stories to cross-functional audiences.
• Ability to analyze and deconstruct complex systems into smaller bits & pieces.
• Well-developed design and research skills, ability to give feedback and mentor designers in growing their technical skill-sets.

Bonus points:

• Ability to solve difficult problems through past work experience and case studies.
• Ability to lead with empathy, transparency, and inclusivity, holding a high bar for accountability and outcomes.

Hi, we're Oscar. We're hiring a Senior Product Designer to join our Product Design 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 Senior Product Designer on the Network Pillar, you will partner closely with product managers, engineers, and operational stakeholders, to design and ship tools that power how Oscar evaluates, manages, and configures its provider network. You will be central to improving operational workflows and decision-making, ensuring internal teams can efficiently assess network adequacy, performance, and provider relationships. The Network Pillar is shaping a suite of new products that bring critical capabilities in-house, helping Oscar ensure its network of providers and services remains comprehensive, high-quality, and accessible to members nationwide. This designer will play a key role in shaping the tools that enable Oscar’s teams to maintain and grow strong partnerships with providers, all while driving a consistent, scalable, and intuitive experience across the company’s network management ecosystem.

The ideal candidate brings strong systems thinking, experience designing SaaS or internal tools, and the ability to work autonomously from discovery through delivery—balancing speed, clarity, and user empathy across complex technical domains.

You will report into the Senior Director, Product Design.

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: $149,040.00 - $195,615.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Own the end-to-end design process (from blue sky thinking to quality specs), balancing polish with speed to execution, with minimal oversight, across various Oscar surfaces.  
• Develop an expert understanding of the users and business domain, informing product strategy and solutions throughout the design process.  
• Collaborate closely with other product designers, product managers, marketers, brand designers, engineers, researchers and others. 
• Play a large role in defining team goals and strategy, connecting the dots between user and business needs.  
• Manage stakeholder relationships, driving towards clarity around decision making.  
• Lead workshops, vision activities or presentations as needed.
• Bring strong visual and interaction design craft, setting a new quality bar for experiences, the wider team, and our design systems.
• Weave the Oscar brand across product experiences.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned.

Requirements:

• 6+ years of experience in Product/UX Design. 
• Concrete examples of designing and shipping complex interfaces. 
• 3+ years managing stakeholders directly. 

Bonus points:

• Experience with the healthcare space.
• Storytelling techniques such as animated prototypes or user flow diagrams.  
• Interest in design ethics, accessibility, and other topics relevant to the healthcare space.
• Genuine and inquisitive, humble yet determined.
• Evidence of design contributions across high-performing web, mobile, or internal tool products.
• Excitement in elevating team through thoughtful coaching and collaboration.
• Proven record of navigating technical constraints to deliver design solutions.   
• Experience with user research and prototyping. 
• Ability to translate requirements, goals, and research into simple and useful UI.

Hi, we're Oscar. We're hiring a Senior Product Designer to join our Product Design 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 Senior Product Designer on the Network Pillar, you will partner closely with product managers, engineers, and operational stakeholders, to design and ship tools that power how Oscar evaluates, manages, and configures its provider network. You will be central to improving operational workflows and decision-making, ensuring internal teams can efficiently assess network adequacy, performance, and provider relationships. The Network Pillar is shaping a suite of new products that bring critical capabilities in-house, helping Oscar ensure its network of providers and services remains comprehensive, high-quality, and accessible to members nationwide. This designer will play a key role in shaping the tools that enable Oscar’s teams to maintain and grow strong partnerships with providers, all while driving a consistent, scalable, and intuitive experience across the company’s network management ecosystem.

The ideal candidate brings strong systems thinking, experience designing SaaS or internal tools, and the ability to work autonomously from discovery through delivery—balancing speed, clarity, and user empathy across complex technical domains.

You will report into the Senior Director, Product Design.

Work Location:

This position is based in our 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: $149,040.00 - $195,615.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Own the end-to-end design process (from blue sky thinking to quality specs), balancing polish with speed to execution, with minimal oversight, across various Oscar surfaces.  
• Develop an expert understanding of the users and business domain, informing product strategy and solutions throughout the design process.  
• Collaborate closely with other product designers, product managers, marketers, brand designers, engineers, researchers and others. 
• Play a large role in defining team goals and strategy, connecting the dots between user and business needs.  
• Manage stakeholder relationships, driving towards clarity around decision making.  
• Lead workshops, vision activities or presentations as needed.
• Bring strong visual and interaction design craft, setting a new quality bar for experiences, the wider team, and our design systems.
• Weave the Oscar brand across product experiences.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned.

Requirements:

• 6+ years of experience in Product/UX Design. 
• Concrete examples of designing and shipping complex interfaces. 
• 3+ years managing stakeholders directly. 

Bonus points:

• Experience with the healthcare space.
• Storytelling techniques such as animated prototypes or user flow diagrams.  
• Interest in design ethics, accessibility, and other topics relevant to the healthcare space.
• Genuine and inquisitive, humble yet determined.
• Evidence of design contributions across high-performing web, mobile, or internal tool products.
• Excitement in elevating team through thoughtful coaching and collaboration.
• Proven record of navigating technical constraints to deliver design solutions.   
• Experience with user research and prototyping. 
• Ability to translate requirements, goals, and research into simple and useful UI.

Hi, we're Oscar. We're hiring a Staff Product Manager to join our AI 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 Staff Product Manager is a senior individual contributor role responsible for defining and driving complex, technical product initiatives with strategic impact across the organization. In this role, you will identify and solve the most valuable business problems through deep user empathy, sharp product intuition, and a strong understanding of Oscar’s operating model and business levers. You will partner closely with engineering, data, and design to lead complex initiatives across domains, aligning directly with senior business leaders on priorities and outcomes. You will act as a force multiplier within the organization—mentoring peers, influencing product practices, and consistently raising the bar on quality, clarity, and impact.

In this Staff Product Manager role, you will focus on AI research and development. You’ll work closely with a small team of engineers and data scientists to explore and prototype new concepts and workflows across Oscar.

You will report into the Senior 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: $180,504.00 - $236,911.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Helping to define the vision, strategy and roadmap for tech components, workflows, and insights that make it easy for teams across Oscar to leverage AI.
• Partnering closely with stakeholders including cross functional department leaders across the business to define strategy and roadmap.
• Collaborating with Engineering and Product leadership to make resource trade-off decisions and to ensure teams are working together effectively.
• Provide recommendations to leadership for product enhancements to improve existing products and development of new ones. 
• Develop operating models for new products in partnership with leadership.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• 7+ years of Product Management experience. 
• 1+ years of Product Management experience in an AI or healthcare setting. 
• Experience building a net new product 0-1. 

Bonus points

• Experience developing AI or ML-related features strongly preferred.
• Experience building AI infrastructure. 
• SQL skills strongly preferred.
• Comfort in working in highly collaborative environments while ensuring the team is always driving towards a decision.
• Excellent analytical and quantitative skills; proved experience using data to identify opportunities, test theories and evaluate success.
• Experience as an end-to-end thinker; the ability to look at a problem and create a solution all the way from top-level goals to smaller details.
• Ability to influence and manage stakeholders at all levels and experience working across all levels of leadership using strong communication and structured thinking.

Hi, we're Oscar. We're hiring a Staff Product Manager to join our AI 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 Staff Product Manager is a senior individual contributor role responsible for defining and driving complex, technical product initiatives with strategic impact across the organization. In this role, you will identify and solve the most valuable business problems through deep user empathy, sharp product intuition, and a strong understanding of Oscar’s operating model and business levers. You will partner closely with engineering, data, and design to lead complex initiatives across domains, aligning directly with senior business leaders on priorities and outcomes. You will act as a force multiplier within the organization—mentoring peers, influencing product practices, and consistently raising the bar on quality, clarity, and impact.

In this Staff Product Manager role, you will focus on AI research and development. You’ll work closely with a small team of engineers and data scientists to explore and prototype new concepts and workflows across Oscar.

You will report into the Senior 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: $180,504.00 - $236,911.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Helping to define the vision, strategy and roadmap for tech components, workflows, and insights that make it easy for teams across Oscar to leverage AI.
• Partnering closely with stakeholders including cross functional department leaders across the business to define strategy and roadmap.
• Collaborating with Engineering and Product leadership to make resource trade-off decisions and to ensure teams are working together effectively.
• Provide recommendations to leadership for product enhancements to improve existing products and development of new ones. 
• Develop operating models for new products in partnership with leadership.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• 7+ years of Product Management experience. 
• 1+ years of Product Management experience in an AI or healthcare setting. 
• Experience building a net new product 0-1. 

Bonus points

• Experience developing AI or ML-related features strongly preferred.
• Experience building AI infrastructure. 
• SQL skills strongly preferred.
• Comfort in working in highly collaborative environments while ensuring the team is always driving towards a decision.
• Excellent analytical and quantitative skills; proved experience using data to identify opportunities, test theories and evaluate success.
• Experience as an end-to-end thinker; the ability to look at a problem and create a solution all the way from top-level goals to smaller details.
• Ability to influence and manage stakeholders at all levels and experience working across all levels of leadership using strong communication and structured thinking.

Hi, we're Oscar. We're hiring a Director, Product Design to join our Product Design 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 strategic Product Design Director to lead a team of designers supporting our internal tools and enterprise ecosystem. In this role, you will oversee the designers building mission-critical platforms that power our business operations. Your mission is to ensure our internal users receive the same high-quality, user-centric experiences as our external customers. As Director, you will uphold a rigorous quality bar, ensuring our tools are not only functional but empower employees to deliver exceptional value to the business and our end-users.

You will report into the Sr. Director, Product Design.

Work Location:

This position is based in our 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: $198,720.00 - $260,820.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Partner with Product and Engineering leads to define area strategy, roadmaps, set measurable goals, and ensure the timely and efficient delivery of high-impact solutions.
• Connect the dots across multiple domains: Network Management, Provider Tooling, and Clinical Experiences, to ensure cohesive, end-to-end ecosystems.
• Propose and lead design-driven initiatives, facilitating discovery and framing long-term strategic opportunities that align with business goals.
• Lead and develop a high-performing team of seasoned designers, fostering a culture of continuous growth and creative excellence.
• Own team resourcing, performance management, and prioritization, optimizing workflows to ensure the team is focused on the highest-leverage work.
• Effectively represent the product design org in executive forums, articulating the rationale behind design directions and highlighting the impact on the business.
• Maintain an uncompromising standard for design execution and craft through direct feedback, design reviews, and hands-on guidance.
• Manage stakeholder relationships, driving towards clarity around decision making and influencing direction through informed insights   
• Focus on scalability by implementing repeatable design processes and contributing to the evolution of a unified design language across multiple domains.
• Contribute to the future of the Product Design and Research function by optimizing our internal workflows, refining our engagement models, and ensuring the team has access to the best-in-class tooling and resources to do great work.  
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Requirements:

• 10+ years of experience in product design, building and shipping applications or software across various experiences.
• 5+ years of experience in a design leadership role, directly contributing and leading people, process, and product strategies.
• Ability to solve difficult problems through past work experience and case studies with evidence of design contributions across power-user interfaces.
• Experience shaping design direction and strategic thinking, identifying goals and opportunities, and making impact-based decisions.
• Engaging presentation skills and the ability to tell compelling stories to cross-functional audiences.
• Ability to analyze and deconstruct complex systems into smaller bits & pieces.
• Well-developed design and research skills, ability to give feedback and mentor designers in growing their technical skill-sets.

Bonus points:

• Ability to solve difficult problems through past work experience and case studies.
• Ability to lead with empathy, transparency, and inclusivity, holding a high bar for accountability and outcomes.