Job Description

Position Summary:

Tokio Marine Highland is seeking a highly skilled and detail-oriented Legal and Compliance Analyst to join our Legal, Risk & Compliance team. This role is critical in ensuring that our insurance operations adhere to all applicable laws, regulations, and internal policies. The ideal candidate will have a strong background in insurance regulatory compliance across all 50 states, including deep experience performing legal research and analysis in admitted and surplus lines laws for P&C insurance markets.

Position Information:

This is a regular, full-time, exempt position in Chicago, IL. This will be a hybrid position, with an expectation of 4 days per week in the office.

Tokio Marine Highland offers competitive salary commensurate with experience and a full suite of benefits including 401(K) with match, generous vacation and personal time, performance-based bonuses, and more.

Key Responsibilities:

• Conduct in-depth research and analysis of 50-state insurance laws and regulations (admitted and surplus lines), delivering timely, actionable insights to Compliance, Legal, and Business teams.
• Monitor and interpret regulatory developments; draft clear, concise summaries and impact assessments.
• Develop and maintain comprehensive compliance tracking tools, including dashboards, reference spreadsheets, and reporting frameworks to ensure visibility and accountability across regulatory obligations.
• Collaborate with cross-functional teams—including Legal, Underwriting, Operations, and Technology—on complex regulatory issues, product launches, and business initiatives.
• Support the Legal team in reviewing and advising on business contracts, including vendor and third-party agreements, with a focus on regulatory compliance and risk mitigation.
• Be a role model of a service-oriented compliance culture by consistently meeting internal service standards—responding promptly, maintaining a positive and collaborative attitude, and building strong working relationships across departments.
• Manage and execute special projects and other duties as assigned, contributing to the continuous improvement of the compliance function.

Required Skills/Abilities:

• Meticulous attention to detail with strong organizational, project management, and time management skills—essential for navigating regulatory and operational complexities in the P&C insurance space.
• Proven ability to manage multiple priorities and deadlines across all service functions.
• Adaptable and resilient in fast-paced, evolving environments typical of insurance operations and regulatory landscapes.
• Results-oriented with a demonstrated ability to work independently and collaboratively across cross-functional teams, including legal, compliance, and risk management.
• Skilled in planning and executing initiatives from concept to completion, with a focus on accuracy and compliance.
• Strong analytical capabilities, including the ability to assess risk, interpret data, and support decision-making in business contexts.
• Demonstrated success in building and maintaining trusted relationships with internal stakeholders.
• Proficient in Microsoft 365 tools (Excel, Word, PowerPoint, CoPilot, etc.), with the ability to leverage them for reporting, analysis, and communication.

Qualifications/Education/Experience:

• Minimum of 5+ years of experience in the insurance industry, preferably within an MGU, MGA, or wholesale/retail brokerage environment.
• Ideal candidate will be licensed attorney or actively pursuing insurance-related designations such as CPCU (Chartered Property Casualty Underwriter), ASLI (Associate in Surplus Lines Insurance), AINS (Associate in General Insurance), or ARC (Associate in Regulation and Compliance).
• Strong working knowledge of personal, commercial, and/or inland marine insurance coverages.
• Deep familiarity with NAIC model laws, surplus lines regulations, and Department of Insurance (DOI) processes is highly preferred.
• Demonstrated experience monitoring, analyzing, and reporting on 50-state and federal insurance laws and regulations.

About Tokio Marine Highland

Tokio Marine Highland Insurance Services (TMH) is a leading property and casualty underwriting agency. We offer a broad suite of tailored specialty risk management solutions, including private flood, fine art and lender-placed products. At TMH, it’s all about our clients. Nationwide, our customers rely on our trusted, industry-leading coverages, supported by compliance expertise, superior claims management and the highest caliber of service.

Founded in 1962, TMH is a wholly owned company of Tokio Marine Kiln, one of the largest carriers in the Lloyd’s of London insurance market and a member of the Tokio Marine Group. TMH has operating centers in Chicago, Il, Frisco, Texas, Miami, Fla., and South Pasadena, Calif.

If you’re looking to advance your career, TMH is the perfect professional home. At TMH, you’ll have a chance to innovate with the world’s leading businesses, put your expertise into action on major projects, and work on game-changing initiatives. You’ll also make long-lasting professional connections through sharing different perspectives, and you’ll be inspired by the best.

Tokio Marine Highland, LLC (TMH) is an Equal Opportunity Employer. TMH’s success depends heavily on the effective utilization of qualified people, regardless of their race, ancestry, religion, color, sex, national origin, sexual orientation, gender identity and/or expression, disability, veteran status, or any characteristic protected by law. As a company, we adhere to and promote equal employment opportunities for all.

Consistent with the Americans with Disabilities Act (ADA) and applicable state and local laws, it is TMH’s policy to provide reasonable accommodation when requested by qualified individuals with disabilities during the recruitment process, unless such accommodation would cause an undue hardship. To make an accommodation request, please contact humanresources@tmhighland.com.

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