INTERVIEW WITH: A (Real) Cowboy. Jason Olbekson. On Sales Leadership, Tech, and Texas Values
A candid conversation with a Texas-born sales leader, on mentorship, masculinity, family, energy careers, and why living fully matters before work. & leading in tech without losing your values ;).
Editor’s note on 11/26: Hi! It’s Fran. This interview was drafted two weeks ago - which to me, is abysmal that I didn’t post until now. However, I took a well-needed mental health break and am continuing to champion my wellness. Please make sure you’re taking care of yourself and others if you can <3
Ryan Watson (Sales leader in Energy & Utilities @ Salesforce - interview coming SOON), Jason and I in Houston!
Cowboy Up: Mentorship, Masculinity, and Building Family in Tech & Energy!
Jason gives me hope in the humanity of men. Not just men… perhaps mankind. Men, women. Everyone.
Jason and I work together at Salesforce, specifically in the Power & Utilities space. As riveting as that sounds (I know ur judging lolz), I’ve genuinely grown to love the industry. Love/hate, as with everything in life. Balance. Yin and yang. There are real opportunities here for collective progress, clean energy initiatives, EVs, and sustainable infrastructure. Cool things happen when you don’t judge a cowboy by his belt. (I made that up off the dome, off the top of my head, for the elders in the room.)
Thank you, Jason, for being, without making this weird, a strong, father-like figure during some ongoing personal challenges I navigate at home. I love my parents deeply; they’re small business owners, immigrants from South Korea, and they did the absolute best they could. Two things can be true at once.
I sat down with Jason over a virtual call to talk about his life. And for a (white) man from Texas, it’s pretty damn cultured and incredible. I don’t know his exact age, but he looks incredibly sharp for someone in his range... and I’ll tell you why: he’s caring and not problematic. Moving on before he cringes himself into another dimension reading this.
Also: don’t knock barbecue. Not into meat? Eat collard greens. I don’t care.
I write all my interviews by hand whenever possible! It helps me retain information better. What follows is what I captured in roughly 45 minutes and nine pages of chicken-scratch notes on a Salesforce-branded notebook. How appropriate. Thank you, Uncle Benioff. Ha ha.
Why This Conversation Matters
Mentorship, masculinity, and family are often talked about separately, but they’re deeply intertwined. Jason’s story shows how one person can balance rugged independence with emotional intelligence, career ambition with care for others, and adventure with stability.
Growing Up Texas
Jason was born and raised in Lubbock, Texas - “tumbleweeds and Buddy Holly,” as he puts it. He describes a Texas mindset of rugged independence, tempered by progressive influences from bigger cities. Houston, for example, was the first U.S. city to elect a lesbian mayor. Annise Parker.
Choosing Energy & Utilities
After college, Jason had to choose between two career paths: writing grants for nonprofits or working at an energy company. He chose stability - leaning into the white picket fence dream and becoming a strong provider.
“They were hiring,” he said with a shrug. (Editor’s note: there’s more to the story, but honestly? Fair.) LMFAOOOOO
Jason entered the workforce at 25, later than traditional expectations, but he and I both agree: you have to live first. You have all the rest of your life to work.
Living Before Working
Jason is low-key a wild Texan. He took a break from college, travelled through Mexico, drained his savings, and came back with a reality check. He fully acknowledges the privilege that allowed him to do this: education, support systems, safety nets. Over seven years, he finished school on and off while backpacking and exploring the world.
Why Salesforce
Jason began at a startup-style software company and eventually realized it wasn’t sustainable. He wanted work to mean more than just sitting in a cubicle. Mentors guided him toward Salesforce, where he found stability, growth, and the chance to make a real impact.
Service Work as a Foundation
Jason paid for much of his travel by bussing tables - a job he calls foundational. It taught him how to de-escalate situations, develop emotional intelligence, and build soft skills you can’t learn in a classroom.
Redefining Masculinity
Family is central to Jason’s life. He has three older brothers and has been married for 14 years. His wife, originally from Colombia, became his partner through mutual friends - a pre-vetted, organic connection. Together they have two children:
A boy into cars, soccer, and games
A girl into K-pop Demon Hunters and early Justin Bieber - definitely a woman of taste!
Jason’s advice for young people dating today? Use your network - it’s pre-vetted, lowers the risk of chaos, and in Texas, the phrase for young men is: Cowboy up.
Building a Global Family
Jason’s mother worked in CPS before developing a private practice. She was adopted, which may have shaped her purpose-driven career. His dad went back to school inspired by her success and earned a graduate degree. Jason’s brothers thrive across HR, IT, and entrepreneurship. Jason himself, the youngest, shares a close bond with his oldest brother - a classic protector vibe.
Jason and his wife navigated a dual-income, no-kids life full of travel, dates, and fun. Adoption came later, and they successfully adopted two babies from Colombia with the help of Salesforce benefits. The process was long and rigorous, including trips to Colombia to complete the adoption.
Where They Are Now
The family is currently in Colombia, testing life abroad to see if it could be a permanent home. Their goal: immerse their children in their roots, culture, and lifestyle, ensuring the right balance between heritage and opportunity.
“You have the rest of your life to work. You don’t always get the chance to live first.”
Jason’s story is a reminder that leadership, mentorship, and masculinity are not about dominance… they’re about care, presence, and showing up fully for your family and community.
If this conversation resonated, share it with someone navigating work, family, or what it means to live fully… PLZ for traffic HAHA <3 xoxo Frances