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Jerry is seeking an Insurance Compliance & Regulatory Senior Lead to join its Insurance Operations team, reporting to the Senior Manager of Insurance Ops. This role bridges customers, carrier partners, state regulators, and internal product teams to solve complex compliance and operational challenges.
Key Responsibilities:
- Lead end-to-end investigation and de-escalation of critical customer complaints, serving as the final escalation point for complex issues
- Manage state Department of Insurance (DOI) and insurance carrier responses, including carrier audits and regulatory complaint workflows
- Author, review, and finalize official correspondence to state departments of insurance, carrier partners, and consumers
- Partner with Legal, Product, and Engineering to convert audit findings and complaint trends into product changes, automated checks, and process fixes
- Own the complaint log and associated workflows, maintaining audit-ready records for market conduct examinations and state data calls
- Serve as primary operational liaison for carrier partners during high-stakes claims investigations and regulatory inquiries
- Provide operational guidance, quality oversight, and subject-matter expertise to team members in customer service, compliance, and claims support
- Maintain accurate, audit-ready records of complaint trends, regulatory correspondence, and resolution timelines to support DOI inquiries and inform leadership of emerging compliance risks
The ideal candidate excels at solving complex systemic issues, building rigorous compliance frameworks, writing with judgment under deadline pressure, identifying root causes, and navigating high-stakes de-escalation with composure and empathy. You naturally spot patterns in complaint data and partner strategically with tech, legal, and ops leaders to fix underlying vulnerabilities.
Jerry is a fintech/insurtech platform that helps over 5 million customers save money on insurance, repairs, and loans. Founded in 2019, the company has become one of the top 3 insurance brokers in the U.S., raised $240M+, achieved profitability in 2024, and is expanding into home, motorcycle, and RV insurance. The company is backed by Y Combinator and led by serial entrepreneurs from Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO.
Requirements:
- Active Property & Casualty (P&C) insurance license required (or willingness to obtain 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 ability to translate regulatory requirements into operational policy and team-level practice
- Exceptional executive-level written and verbal communication skills with attention to 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)
Note: Jerry can only hire full-time salaried employees currently residing in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada.
