Insurance Compliance Analyst

Say hello to Hagerty 

Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do, and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We’re proud to be the world’s largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world’s largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We’re committed to Never Stop Driving. Ready to get in the driver’s seat? Join us!  

As an Insurance Compliance Analyst, you will play an integral role in the compliance program for Hagerty, ensuring that Hagerty promotes an organizational culture that encourages ethical business conduct and a commitment to compliance with the law, resulting in a positive image to associates, customers, vendors, and the community. This position will ensure that sufficient internal policies and controls, reasonably capable of reducing the likelihood of improper conduct, are in place.

As an Insurance Compliance Analyst, you will play a critical role in ensuring Hagerty’s operations meet the highest standards of regulatory compliance. You’ll partner with leaders across the business to provide strategic guidance, support enterprise initiatives, and educate teams on what compliance is and why it is important to our collective success.

In this role, you will conduct legal and regulatory research, support audits and market conduct examinations, and provide advice for regulatory processes associated with our insurance programs. You’ll engage directly with regulatory agencies, ensuring timely and accurate submissions, and maintain second-line monitoring to drive efficiency and reduce risk. By offering compliance insights on enterprise projects, you’ll help align business objectives with evolving regulatory requirements and safeguard Hagerty’s reputation of integrity and excellence.

What you’ll do

• Serve as a strategic compliance partner across the organization, supporting enterprise initiatives and regulatory projects aligned with Hagerty’s long-term goals.
• Provide timely and effective compliance and regulatory support to Claims, Product, Underwriting, Legal, and other business areas.
• Lead cross-functional regulatory initiatives of strategic importance, including enterprise compliance modernization efforts. 
• Independently manage high-impact projects with minimal oversight, ensuring alignment with Hagerty’s strategic goals.
• Conduct legal and regulatory research and deliver actionable guidance to applicable business units.
• Draft and file regulatory filings as required for Hagerty’s insurance programs, including state required filings and holding company act filings.
• Manage state regulatory data calls and regular compliance reporting requirements by gathering required information, validating accuracy with internal stakeholders, and preparing timely, compliant submissions to various state departments of insurance, while maintaining thorough documentation for audit and reporting purposes.
• Monitor and analyze regulatory trends, including Market Conduct Exam findings and enforcement actions, and report emerging risks to leadership.
• Plan and execute Market Conduct Examinations, audits, and Financial Examinations across insurance service areas (claims, underwriting, rating, and finance).
• Identify, assess, and enhance internal controls to mitigate regulatory enforcement risks, collaborating with Internal Audit, Legal, and Compliance teams.
• Develop and implement compliance policies, procedures, and internal controls to educate and support business teams.
• Analyze high-priority regulatory issues and create tracking and monitoring plans to ensure timely and effective solutions are identified and implemented.
• Communicate professionally and effectively with internal and external stakeholders.
• Manage, prioritize, and accomplish multiple tasks within established timeframes.
• Maintain overall general knowledge of insurance industry and Hagerty’s business operations, policies, and procedures.
• Maintain the privacy and confidentiality of information, protect the assets of the Company, act ethically and with integrity, and adhere to Hagerty’s Code of Conduct and policies and procedures.

This might describe you

• Proven, relevant regulatory or insurance compliance work experience.
• Proven experience in regulatory compliance, including leading strategic initiatives with measurable impact.
• Strong analytical, research, and organizational skills, with the ability to interpret and apply insurance laws, regulations, and licensing requirements.
• In-depth understanding of the insurance ecosystem, including relationships among insurers, agents, insureds, MGAs, and regulatory bodies.
• Excellent communication and interpersonal skills, with the ability to build relationships, negotiate effectively, and interact with diverse stakeholders.
• Ability to resolve regulatory and compliance issues with professionalism and sound judgment.
• Highly organized and detail-oriented, with the ability to prioritize, multi-task, and meet deadlines in a fast-paced environment.
• Proficient in legal and compliance research tools (e.g., Westlaw, Oden) and Microsoft Office applications (Word, Excel, Outlook).
• Committed to continuous learning in insurance, regulatory, and compliance disciplines (e.g., pursuing certifications).
• Self-motivated and capable of working independently, exercising discretion and maintaining confidentiality.
• Alignment with company mission and core values, demonstrating integrity and ethical decision-making.

Over and above

• Law Degree and/or advanced insurance certifications, such as CPCU.

Other things to note

• This position is open to U.S. remote work. However, team members who reside within 20 miles of the Traverse City headquarters will follow a hybrid schedule, working from the office three days per week.
• Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable.

If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Cincinnati or Toledo, Ohio, Rhode Island, Washington, British Columbia, Canada please email recruiting@hagerty.com for compensation, comprehensive benefits and the perks that set us apart. 

At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference.  We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world.

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If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!