The Future of Car Insurance, Powered by You.

• Administer the company's equity program in Carta, handling new-hire and promotion grant cycles.
• Prepare board and committee consents and maintain the capitalization table.
• Own the contract intake queue by triaging incoming agreements and tracking them to signature.
• Coordinate with People and Finance on grant data, valuation inputs, and equity reporting.

Contract Review and Management

• Own the contract intake queue: triage incoming agreements, route them for review, and track each through to signature.
• Draft and review NDAs and consulting and independent contractor agreements, and provide first-pass review of vendor contracts.
• Run and maintain the contract audit: catalog active agreements, identify contract owners, and track renewals and key dates.
• Administer the contract management system and keep the electronic document and file management system organized and current.
• Leverage GCAI to conduct first-pass review and redlining of NDAs, consulting agreements, and vendor contracts, flagging non-standard terms for follow-up.
• Use a contract management tool to extract key terms (parties, effective dates, renewal and termination clauses) from executed agreements to populate and maintain the contract audit tracker

​Corporate Governance and Entity Management

• Manage the formation, qualification, and ongoing good standing of the company's entities, including the holding company, the insurance company, Clearcover Financial LLC, and the Clearcover Inter-Insurance Exchange.
• Prepare and file Secretary of State documents, including foreign entity registrations and trade name registrations, and maintain registered agent relationships.
• Prepare materials for and attend Board, Audit, Nominating and Governance, and other committee meetings; draft minutes, resolutions, and written consents.
• Maintain corporate records, entity organizational charts, and governance databases.

Regulatory and statutory filings

• Prepare and file annual statutory filings for the holding company and insurance entities.
• Handle NAIC and state filings for new-state launches and own the annual re-filing calendar, taking ownership of what to file and when to keep the company compliant with NAIC guidelines.
• Support insurance regulatory applications and state DOI portal submissions across states.
• Assist in drafting compliance documents, including protocols, memos, guidelines, audit reports, and market conduct exam responses.

Cross-functional and department support

• Partner with People, Finance, Operations, Insurance Product, Growth, and outside counsel on matters requiring corporate legal support.
• Build and maintain SOPs, process trackers, and self-service tools to keep the department scalable.
• Provide project tracking and administrative support to senior counsel and the broader legal team, including scheduling and deadline management.
• Provide backup support to the claims-legal function as needed, including examination-under-oath scheduling and related coordination.
• Leverage AI to surface relevant case law and generate baseline drafts for routine correspondence.

What do you need?

• Minimum of 5 years of experience as a corporate paralegal in an in-house legal department or law firm.
• Strong drafting, organizational, and project-management skills with discretion in handling confidential matters.
• Proficiency with Google Workspace and Microsoft Office.
• Familiarity with equity administration in Carta or similar platforms.
• Understanding of NAIC filings, state DOI portals, and holding-company structures.
• Experience with mergers and acquisitions or startup-to-exit corporate work.
• Insurance or insurtech experience is a plus.
• Excellent communication skills and the ability to work in a fast-paced environment.
• Detail-oriented with strong problem-solving abilities.

Bonus Points:

• Hands-on experience with debt and equity financing from startup through later stages.
• Familiarity with IPO processes and corporate governance best practices.
• Experience using legal AI tools for administrative efficiency.
• Comfort and/or experience using AI tools (e.g., GCAI) to accelerate contract review, drafting, and filing tracking

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: $45.00-$55.00 (USD) per hour

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.