Senior Insurance Compliance & Regulatory Lead — Remote

Jerry; Chicago (IL); Remote; USD 150,000 - 190,000; Full time

Benefits offered by this job

100% remote work

Full benefits

Equity opportunities

Job summary

Jerry is seeking an Insurance Compliance & Regulatory Senior Lead to join our Insurance Operations team. This role, fully remote in the U.S., reports to the Senior Manager of Insurance Ops and focuses on building rigorous compliance frameworks and solving complex regulatory challenges.

You will lead escalation, regulator communications, and root-cause fixes with cross-functional partners in Legal, Product, and Engineering, while mentoring a compliant, data-driven team.

Qualifications

• 5+ years of insurance experience including regulatory compliance.
• Proven track record managing state regulatory inquiries (DOI) and carrier audits.
• Strong written and verbal communication with legal and regulatory detail.
• Ability to translate regulatory requirements into operational policy and team practice.
• Experience leading a team and mentoring others.
• Familiarity with NAIC model regulations and market conduct standards.
• Bachelor's degree preferred or equivalent leadership experience.

Responsibilities

• Oversee end-to-end investigation and de-escalation framework for complex customer complaints.
• Manage carrier audits and state regulatory complaint workflows; draft official correspondence to regulators and consumers.
• Partner with Legal, Product, and Engineering to translate audit findings into product changes and process fixes.
• Own the complaint log and workflows, ensuring audit-ready records and timely responses.
• Serve as operational liaison for carrier partners during investigations and inquiries.
• Provide guidance and coaching to team members handling customer service and compliance tasks.
• Maintain audit-ready records of trends and regulatory communications to support leadership.

Skills

Insurance compliance

Regulatory knowledge

Leadership

Data-driven

Executive communication

Education

Bachelor's degree

Tools

Regulatory databases

Audit tools

Job description

Jerry is seeking an Insurance Compliance & Regulatory Senior Lead to join our Insurance Operations team. This role, fully remote in the U.S., reports to the Senior Manager of Insurance Ops and focuses on building rigorous compliance frameworks and solving complex regulatory challenges.

You will lead escalation, regulator communications, and root-cause fixes with cross-functional partners in Legal, Product, and Engineering, while mentoring a compliant, data-driven team.