Senior Director, Insurance Product Development and Execution

Responsibilities

• Lead the ACA Individual (QHP) benefit design strategy and portfolio roadmap across operating geographies.
• Manage end-to-end product portfolio performance, including decisions to introduce, enhance, or sunset products.
• Oversee the end-to-end ACA filing program, ensuring accuracy and compliance for PBTs, SBCs, and other regulatory documentation.
• Establish disciplined operating rhythms and scalable workflows to support multi-state execution.
• Lead and develop a multi-level team of directors, senior managers, and managers.
• Partner with actuarial, network, clinical, and compliance teams to achieve growth in a regulated environment.

Requirements

• Bachelor's degree.
• 12+ years of experience in health insurance, product strategy (ACA/QHP focused), and insurance product development.
• 6+ years of people leadership experience managing multi-level teams.
• Deep expertise in ACA individual and small group QHP markets.
• Proven experience leading regulatory filings across multiple markets.
• Ability to travel up to 25% of the time.

Preferred Qualifications

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

Benefits

• Competitive base salary and eligibility for annual performance bonuses.
• Company equity grants.
• Unlimited vacation program.
• Comprehensive medical, dental, and vision benefits.
• 401(k) plan participation and life/disability insurance.
• Paid holidays, sick time, parental leave, and wellness reimbursements.

About the Company

Oscar is the first health insurance company built around a full-stack technology platform and a relentless focus on serving our members. Founded in 2012, we aim to create a health insurance experience that behaves like a doctor in the family.