For Kary Jablonski, becoming CEO of Trucker Tools wasn’t just a career milestone—it was the culmination of lessons learned from years of experiences that shaped her as a leader. From her formative summers at a girls’ camp in Maine to navigating career challenges 10,000 miles away from the office, Kary’s career path reflects resilience, curiosity, and an unrelenting drive to grow.
As she looks to the company’s next chapter of growth with DAT, Kary reflected on the milestones and moments that prepared her for this pivotal role.
Early Leadership Lessons
Kary grew up in the suburbs of Boston with an older and younger brother. She says being the only girl in a male-dominated family challenged her to speak up and hold her own, but that she was not a naturally outgoing kid.
However, that changed when she started going to a summer camp in Maine. It was an all-girls camp with cabins and zero electricity.
“For nine years I went each summer for seven weeks. Being taken out of my day-to-day life where my brothers ran the show and into an all-girls environment was nurturing. I really learned what leadership and leading authentically looks like by understanding how to live and work in a group.”
Kary shared, recounting an experience that taught her the value of building relationships and collaborating with others—skills that carried her through college and into her first leadership roles.
At Georgetown University, Kary honed her interest in business and problem-solving through her work with The Corp, a student-run business that manages the grocery stores and coffee shops on campus.
“Over the three years that I spent working there, the other students became my friends and they inspired my interest in small business. As the general manager for the catering arm, our team fulfilled orders for events on campus. As you can imagine when working with other college kids, we often had to think on our feet if we realized we had misplaced an order or were short a team member. That experience taught me how to problem solve, what it takes to deliver a successful product, and to take risks in a safe space.”
Taking Risks and Gaining Perspective
Kary’s early career took her to Deloitte, where she sharpened her analytical and project execution skills, and later to Uber, where she tackled operational challenges. Her time at Uber brought a defining moment: relocating to Jakarta for a temporary assignment, only to have the office shutter on her first day.
“After a year and a half of working in Uber’s Washington D.C office, I had the opportunity to do a short-term assignment where I’d be working for a few months in Jakarta, Indonesia. I sublet my apartment and moved my life across the globe. Then during my first day in the Jakarta office, Uber announced they were selling their Southeast Asian operation to a competitor and they were going to shut down the office I just set foot in that same day. Learning crazy news while 10,000 miles from home in an office with employees I’d ever met before was an emotional experience that I’ll never forget.
I also experienced an impactful lesson in management and leadership that day. The person who would’ve been my boss on that assignment found me immediately after the announcement, told me to give him my WhatsApp information, and assured me that we’d figure everything out. I think he connected with everyone on the team, but he made me feel seen individually in that moment. Leaders need to make people feel seen and taken care of. The experience was intense, but formative to my leadership approach.”
Discovering a New Path
After returning to the U.S. for an MBA at Kellogg, Kary found herself drawn to Alpine Investor’s CEO-in-Training (CIT) program. “I remembered my experience in Jakarta where I learned that you can’t hang your hat on a specific plan. Having absolute certainty was not nearly as important to me as being confident about the ethos of the program, the people, and the types of problems I would work on.”
Joining the CIT program ultimately led her to ASG and Trucker Tools, where she developed and led a 50-person team toward a shared vision of digitizing the freight industry.
Leading Trucker Tools
Reflecting on her time with Trucker Tools, Kary shared, “I’m proud of how we’ve built on our founders’ incredible vision and product to scale faster than before. We have a massive opportunity to digitize the freight industry, and looking ahead I’m excited that during our time with ASG we were able to launch of our loyalty program, deepened integrations across the freight tech stack, and develop a world-class team.”
Looking towards the future
As Kary and her team look towards their next chapter of growth, she reflected, “This is a tremendous opportunity for Trucker Tools to grow and benefit from the resources, expertise, and market reach of DAT. We’re in an incredible position to shape the future of our industry while unlocking new opportunities for customers, employees, and partners.”
Parts of this interview originally appeared on Alpine Investors.
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