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Rob MacKethan has extensive experience in the insurance industry. Rob currently holds the position of VP of Risk at Second Nature. Previously, they were an Advisor at a Stealth insurtech startup, as well as serving on the Advisory Board of Marketplace Risk. In 2019, they worked at High Definition Vehicle Insurance (HDVI) as an Advisor. In 2022, they served as the Head of Risk Management and Insurance at HyreCar. From 2019 to 2022, they were the VP of Insurance and Risk Management at Lime, where they built a practice dedicated to understanding risk and advancing safety for Lime riders. Prior to that, they held various roles at Zendrive, including Advisor and VP of Insurance, where they focused on measuring and managing driving risk. In 2017, they co-founded Fairmatic, a startup MGA specializing in fleet and embedded commercial auto insurance. Rob also has experience at Answer Financial Inc. (an Allstate company) as Head of New Initiatives and Chief Business Development Officer, where they led innovation initiatives and grew the business to become the largest online insurance comparison shopping service in the country. Rob began their career as the President of Insurance at NetBank.

Rob MacKethan holds a Bachelor of Arts degree in Economics from Yale University. In 2019, they also enrolled in the Leaders In Tech program. Additionally, they have obtained certifications in Property, Casualty, Life & Health Insurance Broker License and Surplus Lines Insurance Broker License, which are recognized in all US states.