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.

About the Role:

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

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 is: $101,844 - $133,670 per year in New Jersey, New York, and California. The base pay for all other locations is: $91,659 - $120,303 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

Product Filing Execution

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

Regulatory Objections & Updates

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

Cross-Functional Coordination

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

Operational Execution & Process Support

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

Data Integrity & Quality Assurance

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

Requirements:

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.

Bonus Points:

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

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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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