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Keith Gillette has over 25 years of experience in the field of information technology and leadership. Keith is the Founder & CEO of TaskTrain, a software-as-a-service startup that focuses on workflow solutions. Keith has also served as the Chief Technology Officer at the Boston Public Library and Awecademy. Additionally, they have worked as a Senior Collaborator at Educational Collaborators and a Senior Advisor at MindBridge Partners. Keith has provided virtual, fractional, and interim CIO and IT consulting services through their company GilletTEK, specializing in educational and non-profit institutions. Keith has also held interim Chief Information Officer positions at Barrie School and McLean School. Keith has extensive experience leading information technology departments as the Director of Information Technology at Lake Forest Country Day School and the Information Technology Manager at Conserve School.

Keith Gillette has a strong educational background with various degrees and certifications. Keith completed their Master of Business Administration with a focus on Entrepreneurship, Strategy, Economics, and International Business at The University of Chicago Booth School of Business from 2008 to 2011. Prior to that, they obtained a Master of Science degree in Information & Telecommunications Systems Management from Capitol Technology University from 2000 to 2004. Keith also holds a Bachelor of Science degree in Philosophy from the University of Wisconsin-Madison, which they earned between 1990 and 1995.

In addition to their degrees, Keith Gillette has obtained multiple certifications. Keith has earned the ITIL 4 Foundation certification from PeopleCert in July 2023. Keith is also a Certified TCP/IP Network Analyst, certified through ACE/PONSI via American Research Group, although the exact date of certification is not provided. Furthermore, Keith holds a Six Sigma Green Belt certification from the American Society for Quality. Specific dates for the last two certifications are not available.