Hi, we're Oscar. We're hiring a Senior Director, Insurance Product Development and 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 Senior Director, Product Development & Execution leads the execution of ACA individual and small group health plan products, with accountability over the product-specific deliverables associated with the regulatory filing lifecycle.

You will manage end-to-end product portfolio performance, spanning benefit design, filings, and go-to-market readiness. It also includes post-launch optimization, while operating a disciplined, multi-state filing program. The Senior Director, leads a multi-level team of product directors, senior managers, and managers, partnering to deliver compliant and scalable products.

You combine product strategy with operational thoughtfulness, ensuring execution, process scalability, and high-quality outcomes across multiple markets.

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 in the states of California, Connecticut, New Jersey, New York, and Washington is: $198,720- $260,820 per year. The base pay for this role in all other locations is:: $178,848- $234,738 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program company equity grants and annual performance bonuses.

Responsibilities:

Product Portfolio Strategy Leadership
- Define and lead ACA Individual (QHP) benefit design strategy and portfolio roadmap across Oscar's operating geography
- Manage portfolio decisions (introduce, enhance, fix, and sunset) based on performance, competitive dynamics, and member needs
- Align product portfolio strategy with enterprise goals for growth, retention, and margin generation
- Partner to develop positioning, go-to-market plans, and sales enablement tools
- Ensure product launches and implementation readiness
Regulatory FIlings & Execution Leadership
- Lead the end-to-end ACA filing program, including product specific deliverable execution across Oscar's operating geographies
- Oversee development and submission of PBT's, SBC's and all other required regulatory documentation
- Ensure accuracy, compliance, and consistency across all filings and supporting artifacts (e.g., plan counts by state, internal system AV agreement)
- Promote coordination to meet critical filing deadlines under leadership and SIO guidance
Operational Excellence & Process Leadership
- Establish and enforce disciplined operating rhythms across product development and filing cycles
- Build scalable processes and workflows to support multi state execution
- Promote standardization, quality controls, and continuous improvement across filings and product operations
- Resolve execution risks, data inconsistencies, and process gaps
- Implement structured reporting to track progress, risks, and performance
People Leadership & Cross-Functional Development
- Partner with actuarial, network, market leadership, clinical, compliance, and operations to achieve growth in a regulated environment
- Promote agreement on product design decisions, trade-offs, and execution priorities by market
- Support executive decision-making through clear and structured insights
- Lead a team of directors, senior managers, and managers
- Establish clear roles, accountability, and performance expectations across the department
- Promote a culture of ownership aligned with process consistency, operational excellence, and continuous improvement
- Compliance with all applicable laws and regulations
- Other duties as assigned

Requirements:

Bachelor's degree.
12+ years experience in health insurance, product strategy (ACA, QHP focused), and insurance product development
6+ years people leadership experience managing multi-level teams
Expertise in ACA individual and small group QHP markets
Experience leading regulatory filings across multiple markets (PBT, SBC, and other documentation)
Willingness to operate in a structured, process-driven environment, driving execution at scale
Experience leading complex programs
Willingness to travel up to 25% of the time.

Bonus points:

Master's degree.
Experience managing National ACA product portfolios
Familiarity in managing third-party vendor relationships and other external partners
Experience in go-to-market strategy and product positioning

This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here.

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

Pay Transparency: Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

Artificial Intelligence (AI): Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.

Reasonable Accommodation: Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team (accommodations@hioscar.com) to make the need for an accommodation known.

California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Privacy Policy.