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Associate Director, Insurance Product Innovation & Emerging Solutions

Oscar · Remote · Posted Jul 8, 2026

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Hi, we're Oscar. We're hiring an Associate 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:

The Associate Director, Insurance Product Emerging Solutions leads the strategy, development, and scaling of innovative health solutions across Oscar's individual market portfolio. This includes product innovation, member incentives, and engagement platforms and emerging solution concepts.

You will lead the translation of enterprise and market strategies into unique, scalable, and compliant product offerings, driving end-to-end product lifecycle performance, from concept through launch, optimization, and growth. The Associate Director partners to provide solutions that improve member experience, retention, affordability, and long-term portfolio value.

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

Responsibilities:

Product Strategy Innovation

Lead the development of product and innovation strategies across the individual market and new solution spaces

Translate enterprise and market priorities into relevant product strategies, value propositions, and expansion roadmaps

Identify and scale new growth opportunities, including lifestyle-oriented products, population-specific solutions, and adjacent offerings

Define market-specific right-to-win strategies, competitive positioning, and investment priorities

Lead development of business cases, including return on investment, growth, and margin impact in partnership with actuarial and finance

Promote optimization of product performance using member insights, behavioral data, and market intelligence

Portfolio Design, Integration, and Lifecycle Ownership

Ensure new solutions integrate with existing product portfolio, benefit design standards, and member value propositions

Improve modular product design to improve scalability, consistency, and speed to market across markets

Manage product lifecycle performance, including launch readiness, post-launch optimization, and long-term sustainability

Partner with product execution, compliance, and regulatory teams to ensure readiness and adherence to all requirements

Incentive Platform Product Partnerships

Build design and execution of the member incentives platform (rewards, engagement programs, and vendor partnerships)

Define and innovate the program structure, eligibility, and value proposition in consideration of member engagement and retention goals

Partner with other teams and external vendors to provide scalable, compliant incentive solutions

Support ongoing refinement post-launch of incentive platform and partnership models, based on data-driven insights to promote membership engagement

Cross-Functional Leadership

Be the senior connector across actuarial, network, market leadership, compliance, regulatory, finance, and growth teams

Promote agreement, ensuring decision-making and execution

Manage dependencies, timelines, and trade-offs alongside peers to ensure execution and delivery of results

Influence strategic decisions across a matrixed organization without direct authority

Lead complex programs spanning multiple markets, partners, and products

Influence decisions and guide progress across a matrixed organization

Analyze results and provide recommendations to improve product performance or scaling of geographies, based on data-driven insights

Provide leadership oversight for direct report(s), including coaching, conducting frequent meetings, direction.

Compliance with all applicable laws and regulations

Other duties as assigned

Requirements:

Bachelor's degree

8+ years of experience in health insurance, product strategy, ACA marketplace, or small group product fields

Experience leading a team without authority and building/developing processes that lead to improved speed to market

Experience supporting or managing product lifecycle execution, including design and launch

Experience working in a matrixed envi…

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