Manager, Insurance Product and Benefit Design

Hi, we’re Oscar. We’re hiring a Manager, Insurance Product and Benefit Design 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 Manager, Insurance Product & Benefit Design supports the development of health insurance plan designs across assigned markets. You will translate market strategy and regulatory requirements into detailed benefit designs, ensuring accuracy across systems, filings, and member-facing materials. This position partners cross-functionally with actuarial, regulatory, network, market leadership, clinical, and operational teams to deliver high-quality, compliance, and competitive health plans.

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: $135,792- $178,227 per year. The base pay for this role in all other locations is:: $122,212- $160,404 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program company equity grants and annual performance bonuses.

Responsibilities:

• Help develop insurance plan designs, including benefits, cost-sharing, and network structures
• Translate strategic direction and regulatory requirements into detailed, executable benefit configurations
• Ensure plan designs are reflected across internal systems and regulatory filings
• Partner with actuarial, regulatory, and compliance teams to validate benefit structures and cost-sharing agreement
• Support execution of the product lifecycle from design through filing, implementation, and launch readiness
• Maintain disciplined operating rhythms across design and filing cycles, ensuring timelines, dependencies, and deliverables are consistently met
• Improve process optimization and standardization across markets to improve scalability, reduce defects, and enhance speed to market
• Lead continuous improvement efforts across product design and filing workflows, identifying inefficiencies and implementing sustainable solutions
• Perform QA across plan designs, filings, and system configurations to ensure accuracy and compliance
• Identify and escalate inconsistencies or risks in design and execution
• Coordinate across partners to ensure accurate delivery of plans
• Support market, competitive, and regulatory analysis to inform plan design decisions
• Help monitor plan performance and identification of improvement opportunities post-launch

• Compliance with all applicable laws and regulations

• Other duties as assigned

Requirements:

• Bachelor’s degree in business, healthcare, economics, finance, or related field
• 5+ years of experience in health insurance product, ACA benefit design, regulatory filings, or related functions
• Operations experience following regimented processes associated with product development and regulatory filing processes, including ability to recommend process improvements for scale and optimization
• Knowledge of the ACA and small group plan design space, including cost-sharing structures, metal tiers, and essential health benefits
• Experience supporting regulatory filings and/or working with filing artifacts (e.g., PBTs, SOBs, SBCs)
• Strong attention to detail with experience managing complex benefit configurations across systems and documentation
• Experience working in cross-functional, matrixed environments (e.g., actuarial, finance, regulatory, network, and operations)
• Demonstrated ability to analyze data and support design and execution decisions
• Willingness to travel up to 25% of the time.

Bonus points:

• Experience configuring or supporting plan builds in product systems
• Familiarity with AV calculators, SBC calculators, and regulatory validation processes
• Exposure to multi-state product environments and varying re…