Hi, we're Oscar. We're hiring an Associate Director, Individual and Family Plan Insurance 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:

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

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.

Pay Transparency: The base pay for this role is: $163,944 - $215,176 per year in New Jersey, New York, and California. The base pay for all other locations is: $147,549 - $193,658 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

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 *

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

Bonus points:

Bachelor’s degree or higher in business, healthcare or quantitative degree

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At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

Pay Transparency: Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

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Reasonable Accommodation: Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team (accommodations@hioscar.com) to make the need for an accommodation known.

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