Senior Director, Insurance Product Development and Execution

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