Episode 16 · Season 1
Jason Pomeroy – Veteran
What do you do after leading soldiers through a nine-day firefight in Afghanistan and watching your story become a combat documentary? In this episode, former Army infantry officer and West Point instructor Jason Pomeroy shares how the mission didn’t end when the bullets stopped, especially as he processed trauma, sought help, and redefined purpose back home. We dig into his role in The Hornet’s Nest, the toll that deployment took on his family life, and the counseling that helped him become a more present husband and father.
What do you do after leading soldiers through a nine-day firefight in Afghanistan and watching your story become a combat documentary? In this episode, former Army infantry officer and West Point instructor Jason Pomeroy shares how the mission didn’t end when the bullets stopped—especially as he processed trauma, sought help, and redefined purpose back home. We dig into his role in The Hornet’s Nest, the toll that deployment took on his family life, and the counseling that helped him become a more present husband and father. Then we follow the winding path that led him from farm kid to major, to startup consultant, and finally to Engagement Manager and change management leader in the Salesforce ecosystem.
Key Takeaways
- 9/11 to Ranger school to Afghanistan – how one high school decision turned into 12 years of service, combat tours, and leadership in the 101st Airborne.
- Inside “The Hornet’s Nest” – the real story behind the documentary: a multi-directional ambush, lost communications, six brothers killed on day one, and a nine-day fight in the Kunar River Valley.
- Calm in the chaos – Jason breaks down what it feels like to realize “no help is coming” and why leaders must still make clear, decisive calls when everyone else is locking up.
- The quiet aftermath of war – from throwing a toy through a wall at home to realizing he needed support, Jason shares how counseling through Headstrong helped him show up better for his family.
- From foxholes to fractional consulting – how he went from no job after separation to building an LLC, closing his own clients, and learning the full life cycle of business the hard way.
- Startup bootcamp for Salesforce – translating requirements between customers and offshore dev teams at a small software company became the perfect bridge to Salesforce consulting.
- Why veterans make elite Engagement Managers – active listening, conflict without drama, owning the budget, and keeping the “wheels on” when timelines and tensions spike.
- Reframing “yes sir” – why the best military leaders don’t want yes-men, and how that same candid, solution-oriented honesty is gold on high-stakes Salesforce projects.
- Purpose after the uniform – Jason’s advice: your biggest task in transition isn’t just finding a job, it’s realigning to a new mission that deserves your level of commitment.
Recommended Links
Jason on LinkedIn
HeadstrongProject.org
Hornet’s Nest Documentary
Cirrius Solutions
ACP
Candorful
Hiring our Heroes
Hire Heroes USA
Merivis
Apple Podcasts
Spotify
Youtube
iHeartRadio
Castbox
Goodpods
Cirrius Blog
Greg Banks on LinkedIn
Jason Fowler Music
For questions or feedback, please contact us at CirriusTalk@CirriusSolutions.com
We cover
- Catalyst of Military Service: The Impact of 9/11
- Experiences in Combat: The 101st Airborne Division
- The Hornet’s Nest: A Personal Story of War
- Life After Combat: Transitioning to Civilian Life and Mental Health
- Leadership Development in the Military
- Transitioning from Military to Business
Chapters
- 0:00Introduction to Jason Pomeroy’s Journey
- 2:51Catalyst of Military Service: The Impact of 9/11
- 5:55Experiences in Combat: The 101st Airborne Division
- 6:42The Hornet’s Nest: A Personal Story of War
- 20:34Life After Combat: Transitioning to Civilian Life and Mental Health
- 26:58Leadership Development in the Military
- 31:24Transitioning from Military to Business
- 33:58Consulting and Entrepreneurial Ventures
- 37:29Skills Transfer from Military to Corporate
- 43:09The Importance of Communication and Conflict Resolution
- 48:16Supporting Veterans in Transition
Jason Pomeroy
Veteran
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