Vice President of Underwriting

As Vice President of Underwriting, you will serve as a strategic and operational leader responsible for underwriting performance, risk selection, and portfolio profitability within the collector and enthusiast vehicle segment. This role combines deep expertise in specialty auto insurance with a passion for automotive culture, ensuring underwriting practices align with the unique needs of collector car owners and the evolving market landscape.

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

Strategic Leadership

• Develops and implements strategic vision for global underwriting and insurance compliance initiatives, consistent with corporate goals and objectives.
• Validates current underwriting processes and develops the roadmap for improved efficiency and quality of underwriting results.
• Provides regular updates to management on key underwriting performance metrics.
• Leads initiatives to modernize underwriting processes through automation, data enrichment, and digital tools.

Underwriting Oversight

• Establishes and maintains underwriting guidelines that reflect the nuances of collector vehicle valuation, usage patterns, and preservation standards.
• Oversees risk selection, pricing adequacy, and portfolio management across all collector auto products.
• Acts as primary point of contact for partner and state or provincial audits and exams and is accountable for results and responses with a goal of achieving satisfactory or better outcomes.

Team Leadership

• Develops a team of underwriters with deep knowledge of specialty auto risks and customer-centric underwriting practices.
• Fosters a culture of continuous learning, innovation, and accountability.

Performance Management

• Monitors underwriting KPIs including segment loss ratios, straight-through-processing rate, post-underwriting performance, and underwriting cost to serve.
• Partners with actuarial and analytics teams to develop and refine segmentation, UW models, and other predictive risk indicators.
• Drives world-class underwriting results through disciplined risk assessment and portfolio optimization while minimizing the administrative burden of underwriting on employees, agents, prospects and customers.

Industry Engagement

• Represents the company in collector car communities, industry forums, and regulatory discussions.
• Maintains strong relationships with regulators, agents, brokers, carrier partners, and affinity partners serving the collector auto market.

Key Competencies

• Bachelor’s degree in Business, Risk Management, or related field (Master’s or CPCU preferred).
• Proven underwriting experience, with at least 5 years in specialty auto or collector vehicle insurance.
• Proven leadership in underwriting strategy, team development, and operational excellence.
• Deep understanding of collector vehicle valuation, usage, and market dynamics.
• Strong analytical, communication, and decision-making skills.

This might describe you

• Personal passion for collector or enthusiast vehicles.
• Experience with agreed value policies, limited use underwriting, and specialty endorsements.
• Familiarity with digital underwriting platforms and Insurtech innovations.
• Ability to balance underwriting discipline with customer empathy and lifestyle alignment.

• 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. 

EEO/AA

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!