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The Daily Scoop Podcast – Episode Summary

Episode: At long last, a new deputy federal CIO
Host: Billy Mitchell
Date: May 11, 2026

Overview

This episode of The Daily Scoop Podcast centers on two major developments in federal government IT leadership and policy. First, it covers the long-awaited appointment of a new Deputy Federal Chief Information Officer (CIO). Second, it delves into the Trump administration’s decision to reorient a key cybersecurity scholarship program—requiring government service after graduation—towards artificial intelligence (AI). The episode explores implications for federal IT leadership continuity and the evolving skills required for future cybersecurity professionals.

Key Discussion Points & Insights

1. Appointment of Thomas Flagg as Deputy Federal CIO

Announcement & Background
- Federal CIO Greg Barbaccia has selected Thomas Flagg, current Chief Information Officer at the Department of Education, as the new Deputy Federal CIO.
- Flagg brings extensive experience: more than 11 years at the Department of Labor, and IT leadership at the Department of Education since October 2024.
- His selection follows “an overwhelming amount of interest in the deputy role from an exceptionally strong field of candidates.” (00:38)
Qualifications & Experience
- Flagg previously held several project management, engineering, and IT positions in the private sector, including work as a Department of Labor contractor.
- Quoting Barbaccia:
  
  "Flagg stood out due to the depth and seriousness of his experience across multiple technology leadership roles, pointing to his time at the Department of Education and DOL." (01:00)
Leadership Gap Filled
- Flagg restores stability to a position left vacant since September 2025, when predecessor Drew Michelgaard exited for the private sector.
- Jay Teitelbaum served as Acting Deputy Federal CIO in the interim, bringing experience from OMB, U.S. Digital Service, and DHS.

2. Cybersecurity Scholarship Program Shifted to AI Focus

Program Overhaul
- The Trump administration has redirected the Cyber Corps Scholarship for Service (SFS) program toward AI, renaming it Cyber AI SFS.
- The change is driven by anticipated AI demands in federal cybersecurity:
  
  “The SFS students we enroll today will not be employable when they graduate in two to three years without significant AI background.” (02:20, quoting the agencies' email)
New Requirements for Scholars
- All new students in the program must now demonstrate AI expertise integrated with cybersecurity, either by using AI tools or safeguarding AI systems.
- Legacy program applicants must describe how they will develop these AI-cybersecurity competencies.
- The agencies involved—Office of Personnel Management (OPM), National Science Foundation (NSF), and Department of Homeland Security (DHS)—had not given advance notice of the change to current participants.
Impact on Current Students
- Some current scholars are dismayed and confused by the abrupt shift, especially with the added pressures of recent cyber job cutbacks and administrative uncertainty.
- Quote from a graduating scholar:
  
  "[I am] disappointed by the change for several reasons." (03:10)
- Approximately 300 students are currently in the program cohort and face uncertainty in meeting new requirements.

Notable Quotes & Memorable Moments

On Flagg’s Appointment:
- Greg Barbaccia (via email, relayed by host):
  
  “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...” (00:48)
On Cyber Corps Program Shift:
- From agency email to program coordinators:
  
  “The SFS students we enroll today will not be employable when they graduate in two to three years without significant AI background. Any SFS student in this new program must be proficient in using AI in cybersecurity or providing security and resilience for AI systems.” (02:20)
Student Perspective:
- Anonymous scholar reaction:
  
  "[I am] disappointed by the change for several reasons. … The email leaves scholars uncertain about what will happen as they try to fulfill their side of the agreement." (03:10)

Timestamps for Key Segments

00:38 — Federal CIO announces Thomas Flagg is named Deputy Federal CIO
01:00 — Barbaccia’s rationale for Flagg’s selection
01:45 — Background on previous deputy and leadership gap
02:05 — Trump officials redirect Cyber Corps SFS toward AI
02:20 — Agencies’ rationale for the AI requirement and official email excerpt
03:10 — Scholar reactions to abrupt program changes
03:30 — Context: program size and job market concerns

Additional Notes

For continued updates on federal government and technology intersections, listeners are advised to visit FedScoop.com.

This episode is an essential listen for those tracking federal IT leadership and the future workforce demands at the nexus of cybersecurity and AI.

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Transcript2 lines

[00:00]
A
Today on the Daily Scoop Podcast from the Scoop News Group. At long last, a new deputy Federal CIO and top Trump officials are steering a cybersecurity scholarship program towards AI. It's Monday, May 11, 2026. Welcome to the Daily Scoop Podcast, where you'll hear the latest news and trends facing government leaders. I'm the host of the Daily Scoop Podcast, Billy Mitchell. Thanks so much for joining me. And now let's dive into the day's top headlines. Federal CIO Greg Barbaccia has tapped the Department of Education's Chief Information Officer as the government's new number two 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 last Thursday to agency CIOs and shared with FedScoop, Barbacci has 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, barbaccio wrote, pointing to his time at the Department of Education and dol. The hiring of FLAG gives the White House its first permanent deputy CIO since September 2025, when when Drew Michelgaard 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. 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 business as a DOL contractor. Now, in other news, the Trump administration is redirecting a cybersecurity scholarship program that requires recipients to work in government service towards artificial intelligence, leaving some current program scholars dismayed and bewildered. In an email to participating school program coordinators obtained by cyberscoop, the Office of Personnel Management and National Science foundation said the Cyber Corps Scholarship for Service program would now be known as the Cyber AI sfs. The email reads, the SFS students we enroll today will not be employable when they graduate in two to three years without significant AI background. Any SFS student in this new program must be proficient in using AI in cybersecurity or providing security and resilience for AI systems. Therefore, new students in the legacy Cyber Corps program must learn to acquire AI expertise to augment their cybersecurity expertise. UNQUOTE the email also explains that new SFS scholars will not be accepted into the Legacy Cyber Corps C program without a description on how they will develop competencies at the intersection of cyber and AI. One current program scholar, graduating soon, said they were disappointed by the change for several reasons. As of earlier last week, the agencies collectively running the program opm, NSF and the Department of Homeland Security hadn't notified any program participants that any changes were on the horizon. The email leaves scholars uncertain about what will happen as they try to fulfill their side of the agreement, especially since doing so has already been difficult amid cyber job cutbacks and other concerns about how the program has recently been administered. There are around 300 people in this current group. For more news at the intersection of the federal government and technology, make sure to visit fedscoop.com
[03:38]
B
thanks so much for tuning in to another episode of the Daily Scoop Podcast, available on all podcast platforms. If you've already rated the podcast on your platform of choice, thanks so much. High ratings and good reviews of the show help more people to find it. The Daily Scoop Podcast is a production of the Scoop News Group in Washington, DC. Adam Butler and Carlin Fisher help put the show together, and the entire Scoop News Group team contributes. We'll be back tomorrow with more top headlines. Until then, I'm your host. As always, Billy Mitchell. Thanks so much for listening.