Keith Gillette is a founder, CEO, and veteran technology leader with 25+ years of experience designing systems, leading IT organizations, and building a SaaS product—TaskTrain—to bring practical process management to teams. Combining dual master’s degrees in systems and business with a philosophy BA, he blends systems thinking and pragmatic strategy to translate complex organizational dynamics into usable workflows and scalable architectures. As a fractional/interim CIO and longtime ed-tech specialist, he’s repeatedly led 1:1 device initiatives, IT transformations, and vendor selections while managing distributed development teams. He currently serves as CTO of Boston Public Library and continues to run TaskTrain, demonstrating a rare mix of hands-on product development, recruiting/outsourcing discipline, and strategic planning. Colleagues know him as a “Process Pragmatist” who enjoys nerding out on theory yet prioritizes solutions that actually get adopted.
9 years of coding experience
19 years of employment as a software developer
Master of Science Information & Telecommunications Systems Management, Master of Science Information & Telecommunications Systems Management at Capitol Technology University
Master of Business Administration Entrepreneurship Strategy Economics International Business, Master of Business Administration Entrepreneurship Strategy Economics International Business at The University of Chicago Booth School of Business
Bachelor of Science Philosophy, Bachelor of Science Philosophy at University of Wisconsin-Madison
Contributions:1 PR, 2 branches in 1 year 11 months
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Keith Gillette - Founder & CEO at Boston Public Library