Senior Director, Insurance Product Innovation & Emerging Solutions

Hi, we're Oscar. We're hiring a Senior Director, Insurance Product Innovation & Emerging Solutions 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:

Lead the strategy for next-generation lifestyle-focused health solutions. These solutions include employer-subsidized, multicultural, disease-specific, and strategic partnership-focused products, such as those with provider, retail, and non-traditional channel-based partnerships.

You will be both a hands-on strategic product leader and people leader, accountable for building a high-performing team while directly leading product strategy and delivery. Translate enterprise priorities into scalable, market-ready health solutions that increase growth, retention, and long-term portfolio difference.

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:

• Insurance Product & Portfolio Innovation Strategies
  • Define and lead the multi-year strategy for new lifestyle product solutions, including employer-subsidized, multicultural, disease specific, and ancillary offerings
  • Set priorities, investment focus, and roadmap (e.g., consumer journey, partnerships, etc.) across the product portfolio
  • Be the senior product owner, directly shaping programs
  Team Leadership & Capability Building
  • Build a team of product manager and strategists
  • Set clear goals, operating rhythm, and accountable for delivery and outcomes
  • Coach team members to operate as end-to-end product owners, not task executors
  • Establish a culture grounded in data analysis, ownership, urgency, and execution focus
  Strategic Partnerships & Lifestyle Ecosystem Development
  • Lead development of culturally aligned and linguistically tailored health solutions
  • Promote disease-specific product development, integrating clinical, network, and journey mapping leading to improved health outcomes for our members
  • Ensure health solutions and lifestyle products are scalable, compliant, and with care for community and market specific needs
  Cross-Functional Leadership & Enterprise Influence
  • Partner with product design, execution and intelligence teams to ensure products are fileable and operationally ready
  • Lead across product, actuarial, markets, network, growth, and strategy teams to implement
  • Promote agreement on priorities, trade-offs, and timelines to create winning products
  • Deliver clear, executive-level recommendations, influencing important decisions; while staying close to the work, stepping in where needed to accelerate quality outcomes
  Performance & Portfolio Management
  • Oversee performance outcomes across growth, retention, affordability, and margin in partnership with market and corporate leadership (e.g., finance, actuarial, network)
  • Make decisions to refine or sunset products, based on market portfolios
  • 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
• Demonstrated ownership of end-to-end product strategy and lifecycle execution
• Experience launching new insurance products, partnerships, or market expansion.
• Willingness to travel up to 25% of the time.

Bonus points:

• MBA, MHA, or other advanced degree
• Experience with employer-subsidized (e.g., small group, mid-group), ACA, and other non-traditional health insurance models
• Experience developing multicultural, population specific, or disease-specific health insurance products