Associate Director, Individual and Family Plan Insurance Solutions
About The Position
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 Associate Director, Individual and Family Plan Insurance Solutions leads complex or multi-market IFP portfolios, owning strategic intent, design coherence, execution quality, and shared accountability for in-market performance alongside leadership. This role functions as a primary decision-maker within defined authority and a senior escalation point for complex design, filing, and execution issues. You will report into the Vice President, Insurance Product Innovation and Development
Requirements
- 7+ years of product management experience, with deep IFP and Small Group expertise
- 5+ years of Previous experience with health insurance product development
- 5+ years experience across multiple markets or complex product lines
- 3+ years making strategic judgment calls and interacting with executive leaders
- Travel up to 25% of the time
Nice To Haves
- Bachelor’s degree or higher in business, healthcare or quantitative degree
Responsibilities
- Product Strategy & Design Leadership Define product strategy and plan design direction for multiple markets or complex offerings
- Translate market strategy, enterprise priorities, and actuarial targets into executable plan designs
- Drive differentiated product concepts while maintaining compliance with enterprise standards
- Maintain tight controls over execution timelines, dependencies, and quality
- Champion innovative, market-differentiated product concepts beyond traditional benefit design
- Leverage quantitative and qualitative analysis to inform strategy, plan design, execution decisions and post-launch performance
- End to End Lifecycle Execution Ownership Oversee end to end plan design and execution across assigned portfolios, including filings and launch readiness
- Ensure cross-market consistency where required while enabling intentional local differentiation
- Partner closely with Actuarial to ensure pricing, actuarial value, and benefit design are fully aligned
- Maintain tight control over execution timelines, dependencies, and quality
- Governance, QA & Approvals Serve as a senior approver for plan designs, filings, and regulatory submissions
- Establish and enforce QA standards, readiness checks, and control points
- Resolve complex regulatory, design, and execution issues; escalate when appropriate
- Post-Launch Ownership Share accountability for live plan performance with leadership and Senior Managers
- Lead cross-market issue remediation, root-cause analysis, and corrective action
- Institutionalize learnings into future design and execution playbooks
- People & Stakeholder Leadership Lead Senior Managers and Managers responsible for market execution
- Act as a trusted thought partner to Market Directors, Actuarial, Network, and Regulatory leaders
- Coach teams on judgement, tradeoff management, and disciplined execution
- Compliance with all applicable laws and regulations
- Other duties as assigned
Benefits
- employee benefits
- participation in Oscar's unlimited vacation program
- annual performance bonuses
- medical, dental, and vision benefits
- 11 paid holidays
- paid sick time
- paid parental leave
- 401(k) plan participation
- life and disability insurance
- paid wellness time and reimbursements
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What This Job Offers
Job Type
Full-time
Career Level
Director
