From Microsoft to Middle School: Damon Fitzgerald’s Unlikely Pivot

In “From Microsoft to Middle School: Damon Fitzgerald’s Unlikely Pivot”, this episode of  @SuccessYourOwnWay  , Yifat Rogers and I sit down with Damon Fitzgerald, a former Microsoft sales executive who made a dramatic career pivot, leaving big tech behind to teach middle school social studies. Damon shares why he made the shift, what he learned from his students, and how his definition of success has evolved. From authenticity and leadership to personal fulfillment and redefining ambition, Damon’s story is honest, inspiring, and full of life lessons (with a few laughs along the way). Whether you’re considering a big life change or just want to hear what it’s like to go from selling tech to wrangling 8th graders, this one’s for you.

Damon’s most recent professional experience was as a middle school social studies teacher in Bloomington, MN. He retired from teaching in 2024 after spending 4 years in this profession.

Before making this pivot to become a teacher, Damon spent over 21 years at Microsoft, where he served in multiple customer-facing roles within the field sales organization. His final role there was leading a sales team covering Microsoft’s Higher Education and K12 customers in the Midwest. He also had roles leading Microsoft’s Enterprise Software business and the Core Infrastructure business, also in the Midwest. He began his career at Microsoft in 1998 as a channel sales manager and also served as a Commercial Account Executive. Throughout his tenure at Microsoft, he earned several awards for excellence.

Before joining Microsoft, Damon was a Senior Consultant at Connect Computer and served as a Senior Consultant with Accenture as a business analyst and developer.

Damon is a native Chicagoan and still has family residing in the Windy City. He lives with his wife Julie, and daughters Janna (21 yrs) and Alecia (17 yrs) in the southeast suburbs. Damon’s community involvement includes service on the Memorial Blood Center Advisory Board and the Osiris Organization board. He enjoys basketball, reading, and traveling with his family. He is a proud booster of the University of St. Thomas basketball team, where he played four years and earned a B.A. in Business.

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