SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Jerry is a fast-growing insurtech platform serving 5M+ customers with AI-powered tools for managing car insurance, repairs, loans, and expanding into home and motorcycle insurance. The company has raised $240M+, achieved profitability since 2024, and is backed by Y Combinator.
You will join the Insurance Operations team as a Senior Lead reporting directly to the Senior Manager of Insurance Ops. This is a strategic individual contributor role focused on building and maintaining rigorous compliance frameworks, managing escalations, and serving as the operational bridge between customers, insurance carriers, state regulators, and internal product teams.
Key responsibilities include:
- Lead end-to-end investigation and de-escalation for critical customer complaints, serving as the final escalation point for complex issues
- Manage state Department of Insurance (DOI) complaint workflows and carrier audit relationships; author and finalize official regulatory correspondence
- Partner with Legal, Product, and Engineering to convert audit findings and complaint patterns into product fixes, automated controls, and process improvements
- Own the complaint log and compliance workflows, ensuring records are audit-ready 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 mentoring to team members in customer service, compliance, and claims support
- Maintain accurate documentation of complaint trends, regulatory correspondence, and resolution timelines to inform leadership of emerging compliance risks
You excel at writing with judgment and clarity under pressure, solving problems at their root, and navigating high-stakes situations with composure and empathy. You spot patterns in data and have the strategic mindset to drive permanent fixes. You thrive in remote environments, bringing organizational rigor and accountability to ensure compliance deadlines are met without exception.
The role is 100% remote with all equipment provided. Jerry is remote-first but maintains offices in Palo Alto, New York City, Chicago, and Toronto if you prefer occasional in-person collaboration.
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 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 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.
