Insurance Compliance & Regulatory Senior Lead

Jerry.ai•Dallas, TX

9d•$70,000 - $100,000•Remote

About The Position

Jerry is seeking an Insurance Compliance & Regulatory Senior Lead for its Insurance Operations team. Reporting directly to the Senior Manager of Insurance Ops, this role leads complex insurance complaint investigations, regulatory and carrier response workflows, and operational compliance controls. The position serves as a strategic liaison among customers, carrier partners, state regulators, and internal teams, and partners with Legal, Product, and Engineering to address systemic issues and improve processes and products. The role also provides operational guidance and quality oversight to team members, maintains accurate audit-ready complaint and regulatory records, and ensures regulatory deadlines and internal service-level agreements are met. This is a 100% remote position; Jerry provides equipment. Applicants must currently reside in an eligible U.S. state or Ontario, Canada, as specified in the posting.

Requirements

Active Property & Casualty (P&C) license, or willingness to obtain it quickly.
At least 5 years of insurance experience, including at least 3 years in state insurance and regulatory compliance.
Proven experience directly managing state regulatory inquiries, including 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 requirements into operational policy and team practices.
Exceptional executive-level written and verbal communication skills and strong attention to legal and compliance detail.
Strong analytical skills and experience using data to drive cross-functional product and operational improvements.

Nice To Haves

At least 2 years in a team lead, managerial, or supervisory role.
Bachelor’s degree, or equivalent practical leadership experience.

Responsibilities

Lead end-to-end investigations and de-escalation for critical customer complaints, serving as the final escalation point for complex issues.
Manage carrier audits and state regulatory complaint workflows; author, review, and finalize correspondence to state departments of insurance, carrier partners, and consumers.
Partner with Legal, Product, and Engineering to turn audit findings and complaint trends into product changes, automated checks, and process improvements.
Own the complaint log and related workflows, maintaining accurate, audit-ready records for market conduct examinations and state data calls while meeting statutory deadlines and internal SLAs.
Serve as the primary operational liaison for carrier partners during high-stakes claims investigations, regulatory inquiries, and information audits.
Guide and coach team members handling customer service, compliance, and claims support through operational guidance, quality oversight, and subject-matter expertise.
Maintain documentation of complaint trends, regulatory correspondence, and resolution timelines to support timely DOI responses and inform leadership about emerging compliance risks.