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: Connect with Courtney Oman on LinkedIn Learn more about Strategic Information Group and internship opportunities Explore Derek’s School of Understanding Build your Professional Podcast Profile Music by Lidérc. #careers #careerpivot #workingmom #salescareer #careeradvice #timeforareset