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From Action Sports to Tech Sales: Reinventing Your Career with Confidence – featuring Courtney Oman

What do you do when your life takes a hard left?

(This episode was recorded live on 3/28/2025)

In this episode of The Underswell, I reconnect with longtime friend and former action sports colleague Courtney Oman, now a thriving Senior Account Executive in the tech space. From her early days at Oakley and Volcom to selling ERP software in the life sciences sector, Courtney shares a bold, honest, and empowering story of career reinvention.

After becoming a single mom in a new city, Courtney realized the career she once loved no longer fit her life.

What followed? A hard reset. No real plan B. No job lined up. Just courage, clarity, and a calendar deadline to make it all work.

She didn’t just pivot—she transformed.

💡 What You'll Hear in This Episode: 

  • Why Courtney walked away from the familiar world of product development and fashion - How she built a sales career from scratch (with no tech background!)
  • The power of thick skin, self-advocacy, and betting on yourself
  • What to do when your plan doesn’t go to plan (and why that’s totally okay)
  • Navigating career changes, parenting teens, and staying open to what’s next 🔥

🔥 Highlights:

  • “My job was to go find a job.” – on quitting without a backup plan
  • How a fashion degree, grit, and storytelling helped her stand out in a software sales interview
  • The difference between being creative and being resourceful
  • Why you should always ask yourself: “What’s the worst that could happen?”

🎧 Who Should Listen:

  • Career changers and pivot-curious professionals
  • Anyone feeling stuck or undervalued in their current job
  • Parents juggling ambition and flexibility
  • Young professionals building resilience and exploring options
  • Sales pros and aspiring account executives

🔗 Links & Resources:

Music by Lidérc.

#careers #careerpivot #workingmom #salescareer #careeradvice #timeforareset