Insurance Compliance & Regulatory Senior Lead

Jerry is the #1 rated app for car owners. We help over 5 million people save money on insurance, repairs, and loans—all in one place. Since 2019, we’ve become one of the fastest-growing tech companies in the U.S.

We are looking for an Insurance Compliance & Regulatory Senior Lead to join our Insurance Operations team. Reporting directly to our Senior Manager of Insurance Ops, this role is ideal for an experienced insurance operations leader who excels at solving complex systemic issues, building rigorous compliance frameworks, and acting as the strategic bridge between our customers, carrier partners, state regulators, and internal product teams.

• You write with judgment, not just accuracy. You can take a complicated file, determine what actually happened, and state a clear, complete, well-supported position under a deadline.

• You solve problems at the root. You love digging beneath the surface to identify root causes and aren't afraid to roll up your sleeves to resolve complex edge cases while mentoring others to do the same.

• You excel at high-stakes de-escalation. You possess executive-level composure and genuine empathy, easily navigating intense situations with customers, state regulators, and insurance carrier leaders.

• You turn friction into product fixes. You naturally spot patterns in complaint data and have the strategic mindset to partner with tech, legal, and ops leaders to permanently fix underlying vulnerabilities.

• You build and maintain operational rigor. You thrive in a remote environment, bringing organization, accountability, and process design to ensure compliance deadlines are met without exception.

• Lead Escalation Operations: Oversee the end-to-end investigation and de-escalation framework for critical customer complaints, acting as the final point of escalation for complex issues.

• Own DOI and Insurance Carrier Responses: Manage carrier audits and state regulatory complaint workflows; author, review, and finalize official correspondence to state departments of insurance, carrier partners, and consumers.

• Systemic Root-Cause Resolution: Partner with Legal, Product, and Engineering to convert audit findings and complaint trends into product changes, automated checks, and process fixes.

• Complaint Log & Compliance Controls: Own the complaint log and the workflows behind it, keeping records accurate and audit-ready for market conduct examinations and state data calls, and meeting statutory deadlines and internal SLAs.

• Carrier Relationship & Claims Support: Serve as the primary operational liaison for carrier partners during high-stakes claims investigations, regulatory inquiries, and information audits.

• Team Guidance & Coaching: Provide operational guidance, quality oversight, and subject-matter expertise to team members handling customer service, compliance, and claims support.

• Regulatory Reporting & Documentation: Maintain accurate, audit-ready records of complaint trends, regulatory correspondence, and resolution timelines to support timely responses to DOI inquiries and to inform leadership of emerging compliance risk areas.

• Active Property & Casualty (P&C) license required (or willingness to obtain it quickly)

• 5+ years of insurance experience, including 3+ years in state insurance and regulatory compliance.

• 2+ years in a team lead, managerial, or supervisory role preferred.

• Proven track record of directly managing state regulatory inquiries (DOI complaints) and carrier audit relationships.

• Working knowledge of NAIC model regulations, state insurance codes, and market conduct examination standards, with the ability to translate regulatory requirements into operational policy and team-level practice.

• Exceptional executive-level written and verbal communication skills with an eye for legal and compliance detail.

• Strong analytical mindset with experience using data to drive cross-functional product and operational improvements.

• Bachelor’s degree preferred (or equivalent practical leadership experience).

• Strategic Leadership & Impact: Work directly with Legal, Product, and Ops leadership to shape Jerry’s operational strategy and customer trust standards.

• 100% Remote Work: Work from home with all equipment provided.

• Full Benefits: Comprehensive medical, dental, vision insurance, and 401(k) matching.

While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.

Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at [email protected]

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.

About Jerry.ai

Jerry is building the first AI-powered advisor to manage all your physical assets.

Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.

We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.

Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.

We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.

We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.