Skip to main content

J. Thomas Gregory

Born and raised in Academy District 20, Thomas Gregory has a passion for the educational process and thrives on helping others succeed. He was a classroom teacher for 11 years, a school administrator for four years, and completed his fourteenth year as the leader for the business operations at Academy District 20 in 2019.

Gregory became our Chief Financial Officer in 2009 and served in that capacity until 2016 when he was named the deputy superintendent/chief financial officer (CFO). In these roles, he identified areas where the budget could be reduced without scaling back staffing and school programming. He also co-facilitated the Growth and Capital Needs Committee and presentations to stakeholders that resulted in successful passage of a $230 million-dollar bond measure in 2016. Gregory also increased the district’s Moody’s credit rating from AA3 to AA2. 

In 2005, Gregory was named the executive director for Business Services, during which time he led changes and revisions to many policies and practices, including labor practices, 403(b) plans, full-day kindergarten tuition-based programs and facility rentals. He was also the co-facilitator of the Long-Range Capital Facilities Planning Committee leading to recommendations for new school placement and construction, existing school renovations, technology upgrades and deferred maintenance. Mr. Gregory, along with the then CFO and superintendent, was integral to the passage of a successful mill levy override tax issue in 2008; this resulted in an additional $14 million annually to the school district.

Gregory joined the Academy District 20 staff in 1991 as a middle school math teacher at Challenger Middle School (CMS). Shortly after, he transferred to Rampart High School (RHS) where he served for 11 years as a math teacher, math department co-chair, football coach, softball coach, baseball coach and, finally, as the RHS Assistant Principal and Athletic Director for four of those 11 years.

Gregory earned his master’s degree in Educational Leadership and his Principal Licensure from the University of Colorado Colorado Springs. He earned his bachelor’s degree in mathematics and his Secondary School Teacher Licensure from the University of Southern Colorado.

He is a member and actively participates in the Colorado Association of School Executives, Association of School Business Officials Int’l, Colorado Association of School Business Officials, Pikes Peak School Business Officials, National Association of Federally Impacted Schools (NAFIS), Board of Directors (Treasurer) for NAFIS-Federal Lands Impacted Association (FLISA), Pikes Peak Area Education Alliance, and National Interscholastic.

Superintendent's Office

Academy District 20 leadership takes its cues from our Board of Education, driving the initiatives that deliver excellence in education.

Superintendent's Office

Academy District 20 leadership takes its cues from our Board of Education, driving the initiatives that deliver excellence in education.
7:30 a.m. - 4:30 p.m., Monday - Friday
Education and Administration Center
1110 Chapel Hills Dr.
Colorado Springs, CO 80920