Senior Director, Insurance Product Development and Execution

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 pr

Benefits

Additional Information

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.

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