How an $18K Job and a Missed Deadline Shaped Microsoft’s Heidi Kobylski into a Federal Tech Leader

Heidi Kobylski didn’t start out in tech or business. She started out helping women rebuild their lives in transitional housing in Baltimore. The work was meaningful, but it also revealed something else: She wanted to create impact in a different way.On this week’s "Rookies to Rockstars," Amanda Ziadeh and Camille Tuutti sit down with Heidi Kobylski, U.S. federal civilian leader at Microsoft, to talk about risk, reinvention and how she built her career one leap at a time.Today, Heidi leads AI and cloud transformation across federal agencies. But getting there meant detours, missed deadlines and a few defining moments like earning her MBA at night while raising twins, one with special needs.We also talked about:• The $18K job that taught her empathy and grit• The government bid she missed by three minutes—and how it changed her perspective• Learning to play the long game instead of chasing perfection• Using data (and courage) to negotiate pay and close the gap• Why “remote only” can limit early-career growth• And the surprising way she finds balance: racing carsTune in for a  grounded, candid conversation about risk, resilience and redefining success in federal tech.