Head of Operations

Position Summary

Location: Frisco, TX (primary; 2–3 days in-office). Open to Chicago, IL for the right candidate.

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This role is anchored in our Frisco, TX office, supporting a key area of operational growth as we continue to scale. We’re seeking a VP-level leader with hands-on operational ownership—someone who brings experience building and scaling operations in more complex environments and can apply that perspective in a growing, mid-sized organization.

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This leader will drive execution, build structure, and partner closely with leadership to evolve our operating model, while helping shape the future organization, including adding leadership layers as we scale. This role reports to the COO and works closely with executive leadership across underwriting, finance, and key business functions.

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Key Responsibilities

• Define and execute the operations strategy aligned with company growth objectives, while remaining close to day-to-day execution. Design and implement a scalable, multi-product operating model, including standardized third-party operations.
• Oversee end-to-end policy lifecycle operations, ensuring efficient underwriting support, policy administration, and broker service.
• Ensure accurate premium processing, bordereaux reporting, and strong fiduciary controls in partnership with Finance.
• Establish operational governance, regulatory controls, and audit-ready processes aligned with delegated authority requirements.
• Manage and oversee third-party vendors and BPO partners to ensure service quality and performance.
• Implement data-driven performance management through operational reporting, KPIs, and service standards.
• Lead pragmatic operational improvements, including automation and AI-enabled workflows where appropriate.
• Build and lead a high-performing, scalable operations function, initially within a lean team structure.

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Experience and Qualifications

• 12+ years of insurance operations experience with progressive leadership responsibility, ideally within an MGA or delegated authority environment
• Strong expertise across underwriting operations, policy lifecycle, premium accounting, and bordereaux reporting
• Experience scaling operations and managing third-party partner
• Data-driven, pragmatic leader with strong stakeholder management and executive presence

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Additional Experience (Preferred)

• Experience scaling an MGA platform or working with multiple capacity providers
• Exposure to policy administration systems and operational tooling
• Experience leveraging automation or AI within operational workflows

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Education

• Bachelor’s degree in Business, Finance, Insurance, Operations, or a related field (advanced degree a plus)

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Additional Job Details:

The pay range for this role is $155,900 - $196,600 + bonus. This range reflects a good faith estimate of pay at the time of posting. Actual compensation will be determined based on factors such as experience, skills, knowledge, education, and internal pay equity.

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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.

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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.

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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.

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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.

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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 peopleandstrategy@tmhighland.com.