In this episode, Rob Reynolds (CIO, Orange County, North Carolina) talks about coming from a big Navy family. His dad served in Underwater Demolition Teams (UDTs), the unit Rob calls the first Navy SEALs, and in the '60s his team was first out to the space capsules to get the astronauts out. Rob followed his dad into the Navy, then spent about 30 years in IT, including 2 turns as a CISO.
Rob shares what happens when you give people the tools, from the AI sandbox behind a staffer's tax calculator idea, to users trained to flag the message that looks like it came from Rob, to a $10M ARPA broadband buildout that has people calling Rob to say thank you.
Orange County also placed #8 in its population category (150,000–249,999) in the 2026 Digital Counties Survey from the Center for Digital Government and NACo, recognition Rob credits to his team's work modernizing county services.
Timestamps
0:00 A Commodore VIC-20 at age 12, then 2x CISO, now county CIO
1:24 His dad's UDT team got astronauts out of Gemini-era capsules
11:36 An OpenAI Teams subscription, branded as the county's AI Innovation Lab
13:44 Copilot Chat for every county user, and learning circles next
17:04 The AI tax calculator: a former tax staffer's idea, live in 1 day
25:33 When "Rob" asks for gift cards, users know to raise their hand
26:36 An annual cyber survey, timed to October, sets the quarterly training
28:19 Even when AI is battling AI, it all goes back to people
31:31 Short training, no jargon, and CISA lunch-and-learns for staff
32:29 The $10M ARPA broadband buildout reaching about 6,000 unserved homes
33:52 The calls Rob gets from families whose kids can now do classes online
36:52 Why Rob still remembers the names of people who pulled him up
Connect with the Guests
💼 Rob's LinkedIn: https://www.linkedin.com/in/robreyn/
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