Insurance Compliance & Regulatory Senior Lead

Jerry.ai•Dallas, TX

5d•$70,000 - $100,000•Remote

About The Position

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.

Requirements

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.
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.

Nice To Haves

2+ years in a team lead, managerial, or supervisory role preferred.
Bachelor’s degree preferred (or equivalent practical leadership experience).

Responsibilities

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.