Senior Director, Insurance Product Development and Execution
Oscar · Remote · Posted Jul 8, 2026
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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 p…