Senior Director, Insurance Product Development and Execution

Hi, we're Oscar. We're hiring a Senior Director, Insurance Product Development and Execution 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 Senior Director, Product Development & Execution leads the execution of ACA individual and small group health plan products, with accountability over the product-specific deliverables associated with the regulatory filing lifecycle.

You will manage end-to-end product portfolio performance, spanning benefit design, filings, and go-to-market readiness. It also includes post-launch optimization, while operating a disciplined, multi-state filing program. The Senior Director, leads a multi-level team of product directors, senior managers, and managers, partnering to deliver compliant and scalable products.

You combine product strategy with operational thoughtfulness, ensuring execution, process scalability, and high-quality outcomes across multiple markets.

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 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

Product Portfolio Strategy Leadership

Define and lead ACA Individual (QHP) benefit design strategy and portfolio roadmap across Oscar's operating geography

Manage portfolio decisions (introduce, enhance, fix, and sunset) based on performance, competitive dynamics, and member needs

Align product portfolio strategy with enterprise goals for growth, retention, and margin generation

Partner to develop positioning, go-to-market plans, and sales enablement tools

Ensure product launches and implementation readiness

Regulatory FIlings & Execution Leadership

Lead the end-to-end ACA filing program, including product specific deliverable execution across Oscar's operating geographies

Oversee development and submission of PBT's, SBC's and all other required regulatory documentation

Ensure accuracy, compliance, and consistency across all filings and supporting artifacts (e.g., plan counts by state, internal system AV agreement)

Promote coordination to meet critical filing deadlines under leadership and SIO guidance

Operational Excellence & Process Leadership

Establish and enforce disciplined operating rhythms across product development and filing cycles

Build scalable processes and workflows to support multi state execution

Promote standardization, quality controls, and continuous improvement across filings and product operations

Resolve execution risks, data inconsistencies, and process gaps

Implement structured reporting to track progress, risks, and performance

People Leadership & Cross-Functional Development

Partner with actuarial, network, market leadership, clinical, compliance, and operations to achieve growth in a regulated environment

Promote agreement on product design decisions, trade-offs, and execution priorities by market

Support executive decision-making through clear and structured insights

Lead a team of directors, senior managers, and managers

Establish clear roles, accountability, and performance expectations across the department

Promote a culture of ownership aligned with process consistency, operational excellence, and continuous improvement

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

Experience Leading Regulatory Filings Across Multiple Markets (pbt, Sbc, And Other Documentation)

Willingness to operate in a structured, process-driven environment, driving execution at scale

Experience Leading Complex Programs

Willingness to travel up to 25% of the time.

Bonus Points

Master's degree.

Experience Managing National Aca Product Portfolios

Familiarity in managing third-party vendor relationships and other external partners

Experience In Go-to-market Strategy And Product Positioning

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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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