Thomas Cowan

Thomas Cowan is a CEO, author, Columbia University faculty member, and co-founder of Deep Business — a platform helping top leaders navigate the decisions that matter most in the age of intelligence.

Tom has served as CEO or board chair across more than ten organizations in technology, not-for-profit, and academic sectors — including CEO of OutlookSoft and board positions supporting investments in Tivoli, PGA-com, and NHL-com. Earlier in his career he held top executive roles at IBM, where he developed the large-organization leadership experience that informs his work with CEOs and boards today.

 

At Columbia University, Tom served as Associate Director of the Center for Technology Management, where he taught in the advanced degree programs in technology management.

 

Through Deep Business — co-founded with Deirdre Silberstein — Tom works with CEOs and board chairs on the topics that are top of mind, critical, and strategic: the age of intelligence, changing marketplaces, board governance, and how to deliver results through uncertainty. The Deep Business podcast, now exceeding one hundred episodes, demonstrates human-machine partnership in real time for senior leadership audiences.

 

His published works include Ahead of the Machine (2026), Do You Fit? (forthcoming, 2026), Strategy Workbook (2022), Business Plan Workbook (2023), and Introduction to Technology Management (2023), among others. Recent engagements include partnering with the Mayo Clinic on AI development and authoring Pro Humanitate in the Age of Intelligence — a strategy paper guiding Wake Forest University's presidential search.

 

Tom studied economics, business, and advanced technology at Wake Forest University, the University of South Carolina, and Columbia University — where he later taught in the technology management program for nearly a decade.

May 2026