
Anna Wheeler on breaking barriers, leadership under fire, and cyber's evolution
From The Watchers by Sentinel Blue
March 24, 2026 · 1h 39m · Episode 39
About this episode
Anna Wheeler discusses her transition from military to cybersecurity, sharing insights on leadership and mentoring.
Episode Description (75 words) From helicopter gunner to cybersecurity strategist, Anna Wheeler’s career bridges the kinetic and digital battlefields. Andy and Anna explore her journey through the military, the lessons of leadership under pressure, and the evolving frontlines of cyber defense. She shares insight into breaking barriers, mentoring the next generation, and why optimism still drives her in a field defined by constant threats. MORE FROM ANNA WHEELER https://www.linkedin.com/in/anna-wheeler-ssaw/ FOLLOW THE WATCHERS Website: https://thewatchers.io LinkedIn: https://thewatchers.io/linkedin Sentinel Blue: https://sblu.us/linked Instagram: https://www.instagram.com/watcherspodcast/ JOIN THE CONVERSATION ON DISCORD https://thewatchers.io/Discord GET THE AUDIO PODCAST RSS Feed: https://thewatchers.io/feed Episodes: https://thewatchers.io/episodes CONNECT WITH ANDY LinkedIn: https://sblu.us/Andy PRODUCED BY https://www.sentinelblue.com PRODUCTION TEAM https://www.brandready.com/ Hashtags: #veteransintech #cyberstrategy #womenincyber #militaryleadership #defenseinnovation #futureofwarfare #operationaltechnology #cyberresilience #thewatcherspodcast #sentinelblue #andysauer…
People in this episode
Host: Andy Sauer
Guest: Anna Wheeler
Topics covered
- cybersecurity
- leadership
- military
- mentoring
- technology
- women in tech
Keywords
- cyber defense
- military leadership
- optimism
- barriers
- future of warfare
Mentioned in this episode
Organizations: Sentinel Blue, The Watchers, Brand Ready, LinkedIn
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