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 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 Program Manager of Diversity, Equity and Inclusion to join our Talent Engagement 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 Diversity, Equity, and Inclusion Program Manager serves as both a strategic builder and operational lead, responsible for advocating for and delivering on increasing equity and inclusion across the entire employee lifecycle and throughout Oscar's People policies and processes. By combining high-level consultancy with hands-on execution, this cross-functional lead operates seamlessly between senior leadership strategy and the operational leadership of our Employee Resource Groups (ERGs). This role is the primary engine behind the programs and initiatives that ensure Oscar's commitment to diversity and inclusion translates into measurable outcomes and a truly equitable culture.

You will report into the Head of Talent Engagement.

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: $117,576-$154,319 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Partner across the People Team to operationalize and integrate DEI best practices throughout all policies and workflows.
• Collaborate across People Team functions (e.g., Recruiting, Compensation, People Ops, Performance, L&D) to help define, integrate, and own their respective Diversity, Equity, Inclusion (DEI) responsibilities, and provide them with support.
• Partner with business leads and teams across the organization to audit operations and policies to ensure they have integrated DEI best practices and guidelines.
• Work with recruiting to ensure processes lead to diverse talent pipelines, and to review and monitor hiring practices, then expand or change them to meet the objective of recruiting candidates from diverse backgrounds.
• Develop and implement co-wide central programs that promote diversity within the company or an organization. This Includes partnership with Programming colleagues (L&D, Culture & Engagement) to ensure employee and culture development opportunities.
• Create and Execute Oscar's Employee Resource / Business Resource Group Strategy
• Serve as the central resource and primary contact for Oscar's Employee Resource Groups (ERGs) by overseeing their day-to-day operations.
• Collaborate with Oscar's ERGs to create and execute executive annual strategic plans that foster community, connection, access and opportunities for professional and personal development.
• Drive ERG success by securing executive sponsors and equipping co-chairs with the strategic influence to lead effectively.
• Be a starting point and facilitator to help kick-off the inclusion and equity-related issues. Step in to be a central point of coordination for solutions/programs.
• Plan, procure and lead live and virtual programming for Oscar employees, including specific groups or communities that focus on inclusive best practices for managers, teams and individual contributors.
• Direct the annual Culturally Competent Care Grant Initiative, including applicant auditing and program evolution to align community impact with Oscar's core health equity and business objectives.
• Work with technology teams or vendors to assess, onboard, or enhance technology
• Measure/monitor important DEI metrics, including working with applicable partners to define relevant benchmarks, thresholds, and targets.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 5+ years of professional experience, with at least 4 years specifically building and executing integrated DEI strategies in a fast-paced or matrixed environment.
• Demonstrated success in integrating DEI best practices within HR functions (Recruiting, Comp, L&D).
• Proven experience scaling ERG/BRGs by aligning them with business objectives and engaging executive sponsors.
• Strong analytical acumen, with experience defining benchmarks and using data to tell a compelling story of progress and ROI.
• Advanced interpersonal and influence skills, with a track record of advising HR partners and senior business leaders.

Bonus points:

• Prior experience in building and leading professional development sessions focused on operationalizing inclusive leadership best practices and psychological safety across diverse teams.
• Master's degree or advanced certifications.

Hi, we're Oscar. We're hiring a Senior Manager, Employee Experience to join our People 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 responsible for designing, delivering, and evolving Oscar Health's physical workplace and culture strategy to create an environment where employees feel valued, inspired, and empowered to do their best work. This role intersects both strategy and execution, overseeing workplace operations across multiple locations, leading a cross-functional team to ensure seamless day-to-day services, and drives high-impact cultural initiatives and events that foster connection, engagement, and a strong sense of belonging. You are a strategic, hands-on leader who thrives at the intersection of facilities management, employee engagement, and culture-building.

You will report into the Head of Talent Engagement.

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: $122,212- $160,404 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

Workplace Operations & Facilities Management

• Oversee Oscar's main office locations as well as ad hoc WeWork and remote workspaces nationwide.
• Lead the workplace operations team to ensure high-quality, consistent service delivery, including mail distribution, food and beverage offerings, office supplies, custodial services, safety, parking, and tenant relations.
• Manage and step in to execute as needed, day-to-day office operations, ensuring spaces are optimized for collaboration, productivity, and employee well-being.
• Maintain strong cross-functional relationships with People, Legal, Finance, Security, Communications, and Executive teams to support evolving business needs.
• Manage team budgets, tools, vendor relationships, and contracts to ensure operational and cost efficiencies.
• Serve as project manager for space development and office branding initiatives, ensuring timely, on-budget delivery.

Culture, Events & Employee Engagement

• Develop and implement a comprehensive employee experience strategy that advances Oscar's mission and values.
• Design and execute engaging internal events and programs (e.g., "Oscar Exclusive Events," volunteer opportunities, wellness initiatives) that foster camaraderie, connection and belonging.
• Partner with leadership and People teams across all locations to ensure a cohesive and inclusive employee experience.
• Curate and manage company perks, office branding, and unique experiences that reflect Oscar's innovative and consumer-centric culture.
• Build partnerships with local organizations, government, and educational institutions to champion Oscar's brand and community involvement.
• Measure and report on the impact of employee experience initiatives, overseeing company wide employee listening strategy (including surveys and focus groups) as well as feedback and data to continuously improve offerings.

Leadership & Team Development

• Lead, mentor, and develop a high-performing team focused on workplace operations and employee experience.
• Set clear goals, roadmaps, and deliverables for team members and cross-functional partners.
• Model Oscar's values and serve as a visible ambassador of the company's culture, both internally and externally.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 7+ years of relevant experience in facilities management, employee experience or related fields.
• 2+ years of people leadership experience.
• 2+ years of project management experience.
• 2+ years of vendor management experience.

Bonus points:

• Experience in event planning, office branding, or community engagement.
• Experience managing multi-site operations and remote/hybrid work environments.
• Strong track record of budget management and contract negotiation.

Hi, we're Oscar. We're hiring a Senior Manager, Employee Experience to join our People 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 responsible for designing, delivering, and evolving Oscar Health's physical workplace and culture strategy to create an environment where employees feel valued, inspired, and empowered to do their best work. This role intersects both strategy and execution, overseeing workplace operations across multiple locations, leading a cross-functional team to ensure seamless day-to-day services, and drives high-impact cultural initiatives and events that foster connection, engagement, and a strong sense of belonging. You are a strategic, hands-on leader who thrives at the intersection of facilities management, employee engagement, and culture-building.

You will report into the Head of Talent Engagement.

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: $135,792 - $178,227 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

Workplace Operations & Facilities Management

• Oversee Oscar's main office locations as well as ad hoc WeWork and remote workspaces nationwide.
• Lead the workplace operations team to ensure high-quality, consistent service delivery, including mail distribution, food and beverage offerings, office supplies, custodial services, safety, parking, and tenant relations.
• Manage and step in to execute as needed, day-to-day office operations, ensuring spaces are optimized for collaboration, productivity, and employee well-being.
• Maintain strong cross-functional relationships with People, Legal, Finance, Security, Communications, and Executive teams to support evolving business needs.
• Manage team budgets, tools, vendor relationships, and contracts to ensure operational and cost efficiencies.
• Serve as project manager for space development and office branding initiatives, ensuring timely, on-budget delivery.

Culture, Events & Employee Engagement

• Develop and implement a comprehensive employee experience strategy that advances Oscar's mission and values.
• Design and execute engaging internal events and programs (e.g., "Oscar Exclusive Events," volunteer opportunities, wellness initiatives) that foster camaraderie, connection and belonging.
• Partner with leadership and People teams across all locations to ensure a cohesive and inclusive employee experience.
• Curate and manage company perks, office branding, and unique experiences that reflect Oscar's innovative and consumer-centric culture.
• Build partnerships with local organizations, government, and educational institutions to champion Oscar's brand and community involvement.
• Measure and report on the impact of employee experience initiatives, overseeing company wide employee listening strategy (including surveys and focus groups) as well as feedback and data to continuously improve offerings.

Leadership & Team Development

• Lead, mentor, and develop a high-performing team focused on workplace operations and employee experience.
• Set clear goals, roadmaps, and deliverables for team members and cross-functional partners.
• Model Oscar's values and serve as a visible ambassador of the company's culture, both internally and externally.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 7+ years of relevant experience in facilities management, employee experience or related fields.
• 2+ years of people leadership experience.
• 2+ years of project management experience.
• 2+ years of vendor management experience.

Bonus points:

• Experience in event planning, office branding, or community engagement.
• Experience managing multi-site operations and remote/hybrid work environments.
• Strong track record of budget management and contract negotiation.

Hi, we're Oscar. We're hiring a Director, Talent Management to join our People 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 of Talent Management is responsible for designing and executing enterprise-wide strategies that drive organizational performance, develop leadership capability, and ensure a strong pipeline of talent. This role is critical in driving successful outcomes in succession planning, performance management, and Learning & Development (L&D) to align Oscar's people strategy with business goals and foster a culture of high performance, continuous learning, and internal mobility.

You will report into the VP, Talent.

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 - $236,912 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 and execute a holistic talent management strategy aligned with Oscar's business objectives and values.
• Lead the design and execution of the organization's succession planning strategy to identify, assess, and develop high-potential talent for critical roles.
• Partner with senior leaders to ensure robust succession plans and career paths are in place for key positions.
• Oversee talent review processes, readiness assessments, and development action plans.
• Oversee the organization's performance management framework, ensuring it drives accountability, engagement, and business outcomes.
• Partner with People Strategy and business leaders to ensure consistent performance standards and feedback practices.
• Continually evaluate and refine performance management tools, metrics, and processes to align with organizational culture and strategic objectives.
• Develop and implement the enterprise learning strategy to build organizational capability and leadership strength.
• Lead the design and delivery of programs supporting onboarding, functional skills, leadership development, and career growth.
• Serve as a change agent for talent initiatives, ensuring clear communication and effective adoption across the organization.
• Provide coaching and guidance to leaders on talent management best practices.
• Oversee vendor partnerships and technology platforms that support learning delivery (e.g., LMS, digital learning solutions).
• Collaborate cross-functionally to ensure talent programs integrate seamlessly with DEI, compensation, and workforce planning initiatives.

• Serve as a trusted advisor to senior executives and HR business partners on talent strategy and development.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 12+ years of progressive HR experience with a focus on talent management, organizational development, or organizational effectiveness
• 5+ years experience managing and developing a team of HR professionals.
• Proven success designing and delivering enterprise-level succession, performance, and L&D initiatives.
• Demonstrated experience building programs from the ground up
• Experience leveraging people data to drive decisions