Flagg is the new federal deputy CIO

Thomas Flagg is the new deputy federal chief information officer. Federal News Network has learned that Federal CIO Greg Barbaccia made the announcement to agency CIOs this morning.

Flagg, who is the Education Department CIO, will replace Drew Myklegard, who left in September to join the private sector after three-plus years in the role.

“We had an overwhelming amount of interest in this position from an exceptionally strong field of candidates. Thomas stood out because of the depth and seriousness of his experience across multiple technology leadership roles, including his successful service at the Department of Labor and, most recently, as chief information officer of the Department of Education,” Barbaccia wrote in an email obtained by Federal News Network. “The last point matters a great deal. 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.”

Jay Teitelbaum has been serving as acting deputy CIO since Myklegard left last fall. Barbaccia thanked Teitelbaum for “steady leadership.”

“Jay has been an indispensable asset to our office and to the broader federal technology community, and I’m grateful that he will continue to contribute his experience, judgement and commitment to this work,” Barbaccia wrote.

Barbaccia didn’t say what Teitelbaum would do next.

As for Flagg, he has spent 13 years working as a federal technology executive and was a contractor before joining Labor in 2013.

Flagg spent more than 11 years at Labor, rising to be the director of the business systems directorate.

He joined the Education Department in October 2024. He oversaw and had to deal with severe cuts to employees working on back-office IT operations. Education doesn’t list a deputy CIO on its website so it’s unclear who would take over for Flagg on an interim basis. An email to Education seeking comment was not immediately returned.

One federal agency technology official, who requested anonymity because they didn’t get permission to talk to the press, said the decision to select Flagg is another sign that federal IT leaders at OMB are realizing they need to work with agencies more closely to drive their priorities.

“Absent leadership who gets how agencies work innately, they will struggle to implement their agenda,” the source said. “This should help them get better buy in from all of us.”

Flagg becomes the seventh permanent federal deputy CIO joining Myklegard, Tim Young, Lisa Schlosser, Mike Howell, Margie Graves and Maria Roat.

The deputy federal CIO has traditionally focused on an assortment of issues depending on their backgrounds and the needs of the federal CIO’s office. Myklegard, for example, had cloud and security in his portfolio, while others like Roat had data and digital modernization.

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