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Joshua J. Pyle, FCAS (he/him/his)

Josh leads Boost’s captive insurance company, Boost Re, including the development and execution of the operation’s innovative captive-as-a-service strategy. Boost Re’s segregated cell structure enables insurtechs, MGAs, and embedded insurance partners that leverage Boost’s infrastructure platform to build and scale full-stack programs with optimal capital efficiency. Josh has over 17 years of actuarial and risk/captive management experience, along with a unique perspective to the industry, having served in a diverse range of technology-focused insurance leadership positions spanning price optimization, demand modeling, commercial and personal lines risk pricing, catastrophe modeling, enterprise risk management, competitive intelligence, gig/sharing economy, and SaaS product management. Josh joined Boost from DoorDash, a high-growth publicly traded on-demand delivery technology company, after spending the past 2 years building and scaling its in-house captive insurance company. Reporting directly to DoorDash’s CFO, Josh built and managed a team of more than 20 full-time insurance professionals and oversaw all risk management, actuarial pricing and reserving, and claims operations within the Insurance & Risk business unit. Prior to that, Josh established himself as a leading expert in cyber risk and insurance in a variety of actuarial and data analytics roles and played an instrumental role in building a number of complex cyber-focused risk and catastrophe models throughout his career, including serving as employee #2 at CyberCube, the leading cyber insurance risk and catastrophe analytics company in the industry. Earlier in his career, Josh held several actuarial roles at leading (re)insurance companies including Allianz, CSAA, and Liberty Mutual. Josh holds a bachelor’s degree in mathematics and economics from Grinnell College, has been a Fellow of the Casualty Actuarial Society since 2011, and currently serves as the President of the Casualty Actuaries of the Bay Area.

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