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Patrick Gillespie

Chief Executive Officer and Founder
About Me

Patrick Gillespie is a service-disabled combat veteran. He struggled during his transition from the military. He founded Boots 2 Cyber to help veterans during and after transition. His vision for Boots 2 Cyber is to help lower veteran unemployment and help fill the cyber talent shortage by creating cybersecurity careers for veterans to thrive in.

Patrick began his career in the security industry in 2005. His professional experience includes information technology, vulnerability and risk assessments, penetration testing, security architecture, as well as incident response. A veteran of the United States Army, Patrick worked in Military Intelligence. Patrick then spent the first eleven years of his civilian career architecting and building high-availability network infrastructure for global manufacturing companies.

Prior to joining GuidePoint Security in March 2022, Patrick worked for a global consulting firm where he led consultants from multiple countries to help Fortune 10, Fortune 50, and smaller organizations identify risks present via vulnerability assessments, network penetration testing, application penetration testing, and cloud compliance reviews. Prior to that, he was the director of an offensive network security team that primarily worked with financial institutions. He worked with executives and the sales team to create a Red Team program and he also helped lead the Digital Forensics and Incident Response program.

Patrick earned a Bachelor of Science degree in Computer Information Systems from Thomas Edison State University and a Master of Science in Computer Information Systems (Concentration: Security) from Boston University and holds several certifications including CISSP, OSCP, and CCNP.

He is also on the Board of Advisors for Boots to Books and Whole Cyber Human Initiative.

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Meet Our Experienced Team Members
Patrick Gillespie
CEO & Founder
Tom Gill
CoS & Co-Founder
Chimeria Gonzalez
CPO & Co-Founder
Paul Cummings
CSO & Co-Founder
Cindy Gaddis
CGO & Co-Founder
Eric Svetcov
CISO & Co-Founder