Guy Filippelli

Guy Filippelli is Managing Partner of Squadra Ventures, an early stage VC fund in Baltimore, MD.   He was most recently Founder and CEO of RedOwl, which was acquired by Forcepoint in August 2017. Prior to RedOwl, Guy co-founded Berico Technologies, a high-end engineering firm that services the federal government, and launched Oxpoint Holdings, an investment arm that has invested in and incubated multiple private ventures. He began his career as a US Army intelligence officer, serving in Korea, Italy, Germany, and Afghanistan,and finishing his service at NSA. In 2007, Mr. Filippelli received the National Intelligence Medallion, the nation’s highest award for non-governmental personnel, for his efforts in Iraq as the analytic lead of NSA’s RT-RG program. He was born in Cleveland, Ohio, holds a B.S. in Economics from the United States Military Academy (USMA) at West Point, and an M.A. in Philosophy, Politics, and Economics from Oxford University, where he studied as a Marshall Scholar. He is Chairman of the Commit Foundation, a non-profit that aims to enable serendipity for transitioning veterans through intimate mentoring workshops and one-on-one transition assistance.  He also serves on the Board of the National Cryptologic Foundation, the University of Maryland BioPark, and the Investment Committee of the France Merrick Foundation.  He lives in Baltimore with his wife, Raina, and two children, Sienna (8) and Luca (6).  Guy is obsessed with genealogy (especially Italian) and truly enjoys food, wine, and struggles with golf and now tennis. 

Our Team

Collectively, the Shift5 team includes leading cybersecurity experts, accomplished analysts and developers, military and government backgrounds, authors, pattern-makers, and more. There’s a lot that makes us unique, but together, we’re united around the shared vision of solving the most pressing cybersecurity issues for trains, planes, and tanks and like to have fun doing it.

Josh Lospinoso

CEO & Co-founder


Michael Weigand

Chief Growth Officer & Co-founder


Joe Lea


E. Egon Rinderer

Chief Technology Officer

Matt MacKinnon

Chief Product Officer

Ralph Kahn

Chief Revenue Officer

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