SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Jerry is a leading AI-powered insurance and asset management platform serving 5M+ customers. The company is seeking an Insurance Compliance & Regulatory Senior Lead to join the Insurance Operations team, reporting to the Senior Manager of Insurance Ops.
In this role, you will serve as the strategic bridge between customers, carrier partners, state regulators, and internal product teams. You'll lead escalation operations by overseeing end-to-end investigation and de-escalation frameworks for critical customer complaints, acting as the final point of escalation for complex issues. You'll own all Department of Insurance (DOI) and insurance carrier responses, managing carrier audits and state regulatory complaint workflows while authoring and finalizing official correspondence to state departments of insurance, carrier partners, and consumers.
You'll drive systemic root-cause resolution by partnering with Legal, Product, and Engineering teams to convert audit findings and complaint trends into product changes, automated checks, and process fixes. You'll own the complaint log and associated workflows, ensuring records remain accurate and audit-ready for market conduct examinations and state data calls while meeting statutory deadlines and internal SLAs. As the primary operational liaison for carrier partners, you'll support high-stakes claims investigations, regulatory inquiries, and information audits.
You'll provide operational guidance, quality oversight, and subject-matter expertise to team members handling customer service, compliance, and claims support. You'll maintain accurate, audit-ready records of complaint trends, regulatory correspondence, and resolution timelines to support timely DOI responses and inform leadership of emerging compliance risks.
The ideal candidate excels at solving complex systemic issues, building rigorous compliance frameworks, and navigating high-stakes de-escalation with executive-level composure. You write with judgment and clarity, dig beneath the surface to identify root causes, spot patterns in complaint data, and turn friction into permanent product fixes. You thrive in remote environments, bringing organization, accountability, and process design to ensure compliance deadlines are met without exception.
Jerry offers 100% remote work with all equipment provided, comprehensive medical, dental, and vision insurance, 401(k) matching, paid time off, paid parental leave, and wellness benefits. The company is backed by Y Combinator, has raised $240M+, achieved profitability in 2024, and is expanding into home, motorcycle, RV, and beyond.
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
- 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
- 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.
