Education IT chief Thomas Flagg hired for deputy federal CIO role

Federal CIO Greg Barbaccia has tapped the Department of Education’s chief information officer as the government’s new No. 2 IT official.

Thomas Flagg will take over as deputy federal CIO after spending more than 11 years at the Department of Labor and leading Education’s IT shop since October 2024.

In an email sent Thursday to agency CIOs and shared with FedScoop, Barbaccia said there was “an overwhelming amount of interest” in the deputy role “from an exceptionally strong field of candidates.” 

Flagg stood out due to the “depth and seriousness of his experience across multiple technology leadership roles,” Barbaccia wrote, pointing to his time at the Department of Education and DOL.

“That last point matters a great deal,” the federal CIO added. “Thomas comes into this role having most recently sat in the Agency CIO seat himself. He understands firsthand the operational realities, constraints, frustrations, and opportunities that agency technology leaders face every day.” 

The hiring of Flagg, first reported by Federal News Network, gives the White House its first permanent deputy CIO since September 2025, when Drew Myklegard left the public sector to become Carahsoft’s executive director of government programs.

Since then, the acting deputy federal CIO position has been held by Jay Teitelbaum, an Office of Management and Budget, U.S. Digital Service and Department of Homeland Security alum, per his LinkedIn profile. 

Before joining the Labor Department in 2013 as a supervisory IT specialist, Flagg spent more than a decade in a variety of private-sector project management, engineering and IT roles, including several stints as a DOL contractor, per his LinkedIn profile.