Jesse McKendry

Jesse McKendry is a seasoned executive in the insurance industry, currently serving as Senior Vice President of Insurance Product at Hagerty since July 2025. Previous roles include Senior Director of Insurance Product Management at GEICO, and Senior Director of Insurance at Lemonade. Jesse has extensive experience at Metromile and Progressive Insurance, where notable achievements included improving market share and profitability across various states. Education background includes an MBA in Finance and Operations from The Wharton School and advanced degrees in Mechanical Engineering and Applied Statistics from Stanford University and Oakland University, respectively. Early career experience encompasses roles in production and engineering at notable automotive companies, including DaimlerChrysler and General Motors.