Gregory Garrett

Chief Operating Officer and Chief Innovation Officer Evolver

Last Reviewed: September 27, 2026

Executive Summary

Gregory “Gregg” Garrett is Chief Operating Officer of Evolver, the Reston, Virginia technology company serving federal and commercial customers in IT modernization, cybersecurity and digital transformation, and Chief Operating Officer and Chief Innovation Officer of its parent, Converged Security Solutions (CSS). He took the newly created COO role in September 2025 to run all federal agency delivery across CSS’s Evolver Federal and eVigilant units. He arrived with more than three decades in government technology: as a senior executive at REI Systems and Peraton, as a retired U.S. Air Force colonel, and as a prolific author and teacher on contract management and cybersecurity.

Career Highlights

• Chief Operating Officer of Evolver and of its parent CSS since September 2025, responsible for federal delivery in enterprise infrastructure, cybersecurity, application development, and physical and electronic security.
• Also Chief Operating Officer and Chief Innovation Officer of CSS, as described by Evolver in February 2026.
• Appointed to the Executive Committee of the ACT-IAC Institute for Innovation in February 2026.
• Previously Chief Operating Officer of REI Systems, directing $250 million in government IT and cybersecurity programs.
• As Vice President of Cybersecurity at Peraton, helped scale its cyber business from $1 billion to more than $4 billion a year.
• More than 20 years as a U.S. Air Force officer on active duty and in the reserves, retiring as a colonel.
• Author of more than 24 books and 160 articles and whitepapers, including Cybersecurity in the Digital Age.

Professional Journey

Garrett served more than 20 years as a U.S. Air Force officer, on active duty and in the reserves, earning 17 medals and badges and retiring as a colonel. Alongside that service he built a parallel career as a writer and teacher on how government buys and runs technology: he has published more than 24 books and 160 articles and whitepapers on technology and government contracting, and has taught contract management, program management, systems engineering, IT and cybersecurity to more than 50,000 professionals. He has served on the faculty of the Air Force Institute of Technology, as an adjunct professor at The George Washington University and as a guest lecturer at Georgetown University.

In industry he has overseen organisations responsible for delivering more than $40 billion in IT, artificial intelligence and cybersecurity contracts. As Vice President of Cybersecurity at Peraton, he helped grow its cyber business from $1 billion to more than $4 billion annually. He then became Chief Operating Officer of REI Systems, directing $250 million in government IT and cybersecurity programs.

In September 2025 Converged Security Solutions, founded in 2018 and backed by private investment firms Hillcrest Holdings, Tecum Capital Partners and Akoya Capital, appointed him to the newly established post of Chief Operating Officer. The job put him in charge of all federal agency delivery in CSS’s two federal business units: Evolver Federal, part of the Reston-based Evolver, founded in 2000, and eVigilant, the Manassas, Virginia integrated security company. CEO Mike Santelli said Garrett combined “the operational discipline of a proven executive with the forward-thinking mindset of a true innovator”. By February 2026 Evolver was describing him as COO and Chief Innovation Officer of CSS, and that month he joined the Executive Committee of ACT-IAC’s Institute for Innovation, the government-industry technology forum that had earlier named him Federal IT Industry Contributor of the Year. He also sits on the George Mason University advisory board for its Cybersecurity Resilience Center.

Education

No education record was found in the first-party sources reviewed.