Associate, Insurance Product & Benefit Execution

Hi, we're Oscar. We're hiring an Associate, Insurance Product & Benefit 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.

The Associate, Insurance Product & Benefit Execution supports the development and delivery of insurance product filings by owning product-specific components of the regulatory filing process for ACA Individual and Small Group (QHP).

This role partners closely with product managers, actuarial, compliance, technology and regulatory operational teams to translate product designs into required filing outputs, leveraging internal systems and tools. The Associate is responsible for ensuring accuracy, consistency, and completeness of product related filing materials, as well as supporting responses to regulatory objections and updates.

This position plays a critical role in enabling timely, high-quality filings by coordinating across teams, managing key deliverables, and maintaining strong operational discipline throughout the filing lifecycle.

You will report into the Vice President, Insurance Product Innovation and Development

• Support development of product-specific components of ACA filings, including benefits, cost-sharing structures, and plan design attributes
• Translate product designs into required formats using internal systems and tools to support simpler filings (e.g., portfolio filing extract tools)
• Ensure accuracy and alignment of product data across filing artifacts and internal systems
• Partner with product managers to validate plan designs and resolve system discrepancies

• Support analysis and resolution of regulatory objections, including DOI and CMS feedback
• Coordinate with Insurance Product, Technology, Compliance, and Actuarial teams to develop and implement required updates
• Execute against objections, timelines, and resolutions to ensure timely responses
• Maintain documentation of changes and decisions for audibility and consistency

• Partner with Product, Actuarial, Technology, and Compliance teams to gather inputs and align on filing related deliverables
• Communicate requirements, timelines, and dependencies clearly across stakeholders
• Support alignment between product design and downstream filing / implementation processes

• Maintain trackers and documentation to monitor filing deliverables, dependencies, and timelines
• Ensure completion and quality of assigned deliverables across multiple markets
• Identify inconsistencies, risks, or gaps in product data and escalate as needed
• Support continuous improvement of filing workflows, tools, and documentation processes

• Validate product data across systems and filing outputs to ensure consistency and compliance with internal processes
• Support QA processes for product-related filing components prior to submission
• Assist in auditing outputs to ensure alignment with approved product designs
• Ensure compliance with all applicable laws and regulations
• Other duties as assigned

• Bachelor's degree in Business, Healthcare, Economics, Mathematics, Statistics, Finance, or related field or equivalent work experience
• 3+ years of experience in product, analytics, strategy, consulting, or insurance-related roles
• Exposure to ACA individual and QHP products (including Small Group)
• Strong attention to detail and ability to manage multiple deliverables simultaneously
• Ability to work cross-functionally in a fast-paced, deadline driven environment
• Experience operating in cross-functional, fast-paced environments
• Strong analytical, structured problem-solving, and communication skills
• Willingness to travel to 25% of the time.

• Familiarity with ACA plan design concepts (e.g., EHB’s, limit language)
• Experience with Oscar internal product configuration and filing systems
• Experience managing trackers, deliverables, and project coordination tasks
• Strong excel and data management skills