Jason Holloway

Jason Holloway is a results-driven technology executive with more than 35 years of experience in information technology, cybersecurity, process improvement, and business continuity.

Mr. Holloway currently serves as the President of WidePoint Global as well as Chief Revenue Officer. At WidePoint, he has been a key member of a multi-year turnaround that transformed the company from disconnected divisions to one fully integrated solution, bringing the highest certifications and accreditations of Cybersecurity and Secured Communications in the world. Beginning in 2017 as the Chief Sales & Marketing Officer, his commercial strategy, portfolio refocus, and operational restructuring helped drive sustained double-digit top-line growth, consistent EBITDA positivity, significant margin expansion, and the elimination of corporate debt.

He guided sales and delivery on multiple marquee contracts and large-scale programs, including WidePoint’s two-time incumbent, single-award DHS CWMS contract—where WidePoint serves as the System of Record on a contract valued at $754 million—the U.S. Postal Service engagement covering approximately 35,000 locations, the U.S. Census 2020 Decennial Device as a Service (the largest mobility project in the U.S. at the time), and System of Record services for one of the U.S. ‘s top three carriers. Mr. Holloway also standardized sales and delivery processes, shifted the product mix toward higher-margin managed services and subscription offerings, and executed strategic partnerships and integrations to accelerate capability and recurring revenue. He regularly supports investor relations alongside the CEO through IR conferences, public speaking, and financial analyst Q&A.

After an honorable discharge from the United States Air Force, Mr. Holloway was recruited to lead Networked Knowledge Systems (NKS) as President and CEO; Mr. Holloway scaled the Linux-based managed security business, growing top-line revenue 800% to $63 million in five years while delivering enterprise security services to the healthcare and finance sectors. He later co-founded Nexcentri, and as President and CEO, grew the company from its inception to $500 million in revenue while providing cybersecurity, product development, and managed IT services to the credit union industry and international banking.

Mr. Holloway combines deep technical credibility with commercial rigor, translating complex security and PKI capabilities into scalable, customer-facing services. He brings extensive vertical experience across government, finance, transportation, healthcare, entertainment, and manufacturing, and a proven track record of scaling teams, winning enterprise contracts, and driving predictable, margin-enhancing growth.