Tom Flanagan helps organizations embrace the future without losing their humanity.

Tom is a technology executive, AI strategist, author, and speaker with more than two decades of experience helping organizations navigate technological change and prepare for what’s next. As Chief Digital Information Officer at RE/MAX Holdings, he leads AI, engineering, data, cybersecurity, business applications, and IT operations for a global real estate franchisor supporting approximately 149,000 real estate professionals.

At RE/MAX, Tom oversees a $50 million technology portfolio and a 140-person technology organization. His work has included realigning the technology organization, unifying engineering, reshaping the company’s data approach, and leading enterprise AI strategy, governance, and adoption. A major data restructuring delivered approximately $10 million in annual savings while creating a more flexible foundation for product innovation and AI.

Tom is particularly interested in the human side of technological change. He believes technology should be useful, improve people’s lives, and amplify the human experience. As organizations navigate the rise of AI, he believes closing the AI Trust Gap is one of the most important challenges leaders face. His approach helps people use AI to spend less time on administrative work and more time serving customers, building relationships, and doing the work that matters most.

A longtime industry voice, Tom spent five years as a syndicated technology columnist for Inman News and has spoken at AI4, the Google IT Summit, Microsoft CIO Summit, Inman Connect, and Buzz Amplify. In 2025, he was named to the T3 Sixty Swanepoel Power 200.

Tom is also a published author and recently completed Max Creek: A Rumor in Their Own Time, a biography of the legendary New England rock band Max Creek exploring community, culture, and longevity.