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Charles Fleet

Evergreen, Colorado, United States

Charles Fleet is a practitioner-executive who believes that the fastest path to operational excellence and delivery results is through unlocking the latent potential of the workforce. He specializes in helping organizations navigate the intersection of complex digital transformation and human capability.


Currently serving as the Chief Technology and Digital Transformation Officer at Midwest Housing Equity Group (MHEG), a leading LIHTC syndicator, Charlie leads the strategic vision and execution of technology initiatives.


Prior to MHEG, Charlie served as Chief Transformation Officer for Solera and held executive leadership roles at Travelport and CGI. With over 25 years of experience, he has managed global portfolios and led large-scale integrations, consistently delivering triple-bottom-line results: profitable growth, delighted customers, and a thriving workforce. 


Based in Evergreen, Colorado, Charlie is constantly playing catch-up with his two mischievous sons and his “rocket scientist” wife. He is active in his local community as a Scout leader and occasionally runs marathons.

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Learn More About Charlie

Unlike traditional executives who lead solely from the boardroom, Charlie operates as an internal teacher and mentor. 


He has delivered over 20 hands-on classes and workshops to his internal teams, ranging from Agile delivery to recent deep-dives on artificial intelligence, fostering a “tech-curious” environment that drives efficiency.

Charlie holds a Master of Engineering from the Massachusetts Institute of Technology (MIT) and a Bachelor of Science in Civil Engineering with Distinction from the Virginia Military Institute (VMI).


Language(s): English

Articles, Podcasts & More Featuring this ALJ Guide

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Blog: When Priority Management Becomes a Game You Can't Win

By ALJ Alumni Community • January 27, 2026
Are you playing ping pong or dealing poker? Discover how leaders transformed priority chaos by bringing stakeholders together to negotiate peer-to-peer.
book cover of the book the anatomy of peace

The Anatomy of Peace: Resolving The Heart of Conflict

By Charles Fleet • June 27, 2023
Discover insights and tools for resolving conflict, fostering peace, and transforming relationships with The Anatomy of Peace: Resolving The Heart of Conflict.
A financial statement on a table with colorful folders and a hand holding a pen.

Funding for Improved Business Agility

By Charles Fleet, JP Puttaswamy, and Pete Behrens • March 3, 2023
While there is nothing inherently wrong with gathering departmental leaders into an intense offsite to redistribute funding, there are also limitations that shouldn’t be overlooked. Politics and pet projects overtake strategic priorities, baselining on last year’s budget for next year biases existing programs over new programs, and it tends to drive competition (win/lose) over co-creation (win/win).
An open book on a table. A high-rise building is visible through the window in the background.

Reading — Freedom to Be Happy by Matt Phelan

By ALJ Community • November 18, 2022
Does happiness really impact business outcomes? The ALJ Community discusses the book, Freedom to be Happy, by Matthew Phelan.

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