The Future of Car Insurance, Powered by You.

Clearcover is revolutionizing the industry, putting our customers in the driver's seat. Founded in 2016, Clearcover is built on a simple premise: provide affordable, hassle-free car insurance with one of the industry's fastest claims experiences. We challenge the status quo, redefining what it means to truly put the customer first.

We're rapidly growing and recognized for it! Clearcover has been featured on the Inc. 5000 Fastest Growing Privately Held Companies list and the Deloitte Technology Fast 500™ list, raising over $560 million in funding to date.

We've also been honored on Insurance Business America's Top Insurance Employers list and CNBC's World's Top Insurtech Companies, with Forbes naming us one of America's Best Insurance Companies in 2025.

But what makes Clearcover truly different is our people. We're a team of curious, compassionate problem-solvers who believe that doing right by our customers and each other is just good business.

What will you do?

Clearcover is looking for a motivated, organized problem-solver to join a small, fast-moving Insurance Product team. The Insurance Product Analyst supports the performance, pricing, and regulatory execution of our personal auto products across multiple states — including the forms and filings that bring our changes to market. This role sits at the center of how the team runs: you’ll keep the book’s performance visible, help get rate and rule changes filed and approved, and dig into the analytical questions that drive our next move. You’ll work side by side with Actuarial Pricing, line management, Growth, Claims, and Product Technology.

• Prepare, submit, and track rate, rule, and policy form filings in SERFF, and help respond to regulator objections — ensuring what we file is reasonable, adequate, and compliant
• Monitor profitability and performance for assigned states using standard industry metrics (top-line and bottom-line), and report out monthly with clear commentary on what moved and why
• Investigate performance questions end to end: pull the data, sanity-check it, find the driver, and recommend an action
• Monitor competitor rates, filings, and products, and translate findings into implications for our pricing and product decisions
• Support the policy forms program: maintain the status of forms by state, help draft and revise forms and endorsements with Legal and Compliance, and keep forms, rates, and effective dates in sync for state launches and product changes
• Build templates and processes to gain efficiencies across the Insurance Product function
• Review analytical output for accuracy and be able to explain and defend results to non-technical audiences
• Keep project work organized across many moving parts: track deliverables, deadlines, and owners, and keep the team and leadership informed
• Collaborate with Growth, Product Technology, Claims, Legal, and Compliance on cross-functional projects and launches
• Document processes and maintain Insurance Product documentation so the team can scale
• Use AI tools actively and with good judgment to accelerate analysis, surface pricing and performance insights, and improve efficiency across Insurance Product workflows

What do you need?

• Bachelor’s degree, or equivalent education, training, and work-related experience
• 2+ years of relevant work experience in insurance, analytics, product, or a closely related field
• Strong Excel skills and comfort working with large datasets from multiple sources; ability to read, sanity-check, and explain data
• Working knowledge of insurance data and metrics (loss ratio, frequency/severity, rate change, retention, etc.)
• Strong problem-solving ability and attention to detail
• Strong organizational skills and the ability to manage multiple priorities in a dynamic environment
• Clear written and verbal communication, including regulator-facing and leadership-facing writing, and the willingness to challenge the status quo
• Alignment with Clearcover core values
• Hands-on experience using AI tools to do real work, with good judgment about when to trust the output and when to check it — required, not optional

Bonus Points:

• Personal auto or P&C insurance experience
• Experience with SERFF, policy forms, rate filings, or regulator objection responses
• Experience with Airtable or a similar requirements-tracking tool
• Demonstrated experience building AI-assisted workflows, automated reporting, or analytics tooling in an insurance or product environment

Physical Requirements: Prolonged periods of sitting at a desk and working on a computer

But wait, there's more…

As a people-first company, your health and well-being is a priority at Clearcover. We offer comprehensive benefits and perks for all employees:

• Medical: Affordable BCBS plans for you and your dependents. If you select the high deductible health plan, we offer an HRA and contribute to your HSA.
• Dental and Vision: We cover 100% of dental and vision premiums for you and your dependents.
• Pre-tax benefits, disability, and life insurance
• 401(k): We contribute 3%, even if you contribute nothing.
• Generous vacation, 12 paid holidays, and parental leave
• Equity in the company and an annual bonus program
• Employee auto insurance discount (if Clearcover is available in your state)

We're a remote first company, having paved the way for flexible work locations. If you're local or visiting Chicago, you're also welcome to work from our HQ office.

Base Compensation Range: $85,000 - $105,000 (USD) annually

We encourage all applicants to apply, even if you don't meet every qualification listed. Research shows that underrepresented candidates — including women, people of color, and members of the LGBTQ+ community — are less likely to apply unless they meet 100% of the requirements. Don't let that be the reason you miss out. We want to hear from you.

Clearcover is an Equal Opportunity Employer (EOE) that welcomes and encourages all applicants to apply regardless of age, race, color, religion, sex, sexual orientation, gender identity and/or expression, national origin, disability, veteran status, marital or parental status, ancestry, citizenship status, pregnancy, or other reasons prohibited by law.

Apply for this Position