Vice President of Underwriting

As Vice President of Underwriting, you will serve as a senior technical underwriting expert and strategic advisor within the Corporate Underwriting team. This individual will drive profitable growth through advanced risk evaluation, specialized referral management, product development consultation, and mentoring of underwriting staff/Private Client team members. The role combines deep technical expertise, leadership in underwriting philosophy, and a strong ability to manage complex, high-value, and CAT-exposed risks.

Ready to get in the driver’s seat? Join us!

Advanced Underwriting & Referral Management

• Make and oversee standard underwriting decisions across complex risks.
• Review and approve supercar referrals, including those failing SCSS or lacking RUV documentation.
• Manage 26-point Eligibility file referrals and other high-level exceptions.
• Lead Adverse Action decisioning and compliance, ensuring alignment with regulatory requirements.
• Serve as the lead underwriter for risks above defined TIV thresholds (e.g., $10M+), working directly with Risk Advisors to develop robust risk profiles.
• Evaluate PCS underwriting decisions and provide high-level consultation on challenging submissions.
• Handle various CAT-exposed situations where TIV exceeds $1M and alarming threshold referrals.
• Oversee overseas shipping and Visiting Collectors risk evaluations.

Regulatory & Filing Expertise

• Provide filed UWGL support and craft responses to regulatory objections.
• Maintain deep knowledge of filing requirements, ensuring compliance with all state and national insurance regulations.
• Manage and consult on third-party report contracts (e.g., CLUE, MVR, Risk Meter) and ensure cost-effective and compliant utilization.

Audit & Reinsurance

• Lead and execute underwriting audits, including Markel UW audits conducted bi-annually.
• Provide reinsurance expertise, assisting in the transition of full program and facultative (FAC) reinsurance arrangements from partner carriers to Hagerty.

Strategic Underwriting Leadership

• Assist in shaping Private Client Underwriting philosophy and long-term direction, balancing client profile considerations with market influence and portfolio composition.
• Mentor Private Client team members on holistic risk assessment and profile underwriting, leveraging historical insight and market data.
• Drive the advancement of rating structures and tiers/segments (e.g., $500K–$1M, $1M–$3M, $3M–$5M).
• Consult on new product features, rating algorithms, and policy language to enable profitable growth and competitive positioning.
• Develop geographic rating zones to manage aggregation of risks and determine when mandatory deductibles are required.

Training & Development

• Provide 1-on-1 and group training for underwriting team members on complex risk evaluation and Private Client practices.
• Serve as an internal subject matter expert for high-net-worth underwriting strategies and advanced risk segmentation.

Key Competencies

• Strategic and analytical thinker with a deep understanding of high-value personal insurance risks.
• Ability to balance growth and profitability while maintaining underwriting discipline.
• Collaborative and influential leader capable of shaping underwriting philosophy and direction.
• Detail-oriented with exceptional organizational and decision-making abilities.

This might describe you

• Proven experience, including progressive underwriting experience within high-net-worth or Private Client personal lines insurance.
• Proven expertise in complex risk evaluation, including high-TIV and CAT-exposed risks.
• Strong knowledge of regulatory filings, compliance, and reinsurance structures.
• Demonstrated ability to mentor and train underwriting professionals.
• Track record of managing audits and third-party vendor relationships.
• Excellent analytical, negotiation, and communication skills.

• This role can be worked from any U.S. remote location.
• 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.

Hagerty is an automotive enthusiast brand and the world’s largest membership organization. Along with being a best-in-class provider of specialty insurance for enthusiasts, Hagerty is also home to the Hagerty Drivers Foundation, Garage + Social, Hagerty Drivers Club, Marketplace and so much more. Committed to saving driving for future generations, each and every thing Hagerty does is dedicated to the love of the automobile.

Hagerty is a rapidly growing company that values a winning culture. We provide meaningful work for and invest in every single team member.

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.

If you reside in the following jurisdictions: California, Colorado, District of Columbia, Hawaii, Illinois, Maryland, Minnesota, Nevada, New York, New Jersey, Ohio, Rhode Island, Vermont, Washington, or Canada please email [email protected] for compensation, comprehensive benefits and the perks that set us apart. 

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US Benefits Overview

Canada Benefits Overview

UK Benefits Overview

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