2026 Virginia C-Suite Awards: ROBERT OSMOND

Following his appointment by former Gov. Glenn Youngkin in 2022, Osmond oversaw a significant expansion and modernization of the Virginia Information Technologies Agency as the state’s chief information officer. Drawing on more than two decades of experience — including 15 years at IBM and seven years as CIO of the Virginia Department of Transportation — he led IT infrastructure, cybersecurity, procurement and government services for 65,000 knowledge workers across 67 executive branch agencies.

In May, Osmond was confirmed as the CIO of Delaware, leading its Department of Technology & Information.

During his tenure, VITA expanded network capacity by 1,800% across 1,200 locations and rebuilt the commonwealth’s public cloud data centers. The agency has also countered more than 500 million cybersecurity attacks, modernized over 100 state websites and reduced permit processing times by 70% through the Virginia Permit Transparency system. Osmond also led the launch of Virginia’s first statewide AI governance framework, while growing VITA’s workforce from 210 to 350 employees.

“Bob has reshaped statewide technology strategy, strengthened cybersecurity
and elevated the commonwealth’s digital capabilities to a national leadership position,” says nominator G. Thomas White, manager of infrastructure program services at VITA.

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