The FreightCaviar Podcast: From Camp Counselor to CEO

In this week’s episode, we sat down with Kary Jablonski, CEO at Trucker Tools, a carrier capacity and relationship management platform. Kary takes us through her journey, shares the future plans for Trucker Tools, discusses their mobile app, and provides insights on becoming a better leader. 

Early Inspiration at Summer Camp

Growing up in Boston, Kary spent her summers working at an all-girls summer camp. The experiences she had there ignited a passion for fostering a sense of community, inspiring her to seek out more opportunities to create and nurture similar connections. This passion led Kary to work for The Corp at Georgetown, the nation's largest student-run business, during college. They ran coffee shops and grocery stores, and Kary was part of the catering service on campus. “What I loved about it was, you got to make the calls and decide, ‘We're doing this. We're changing this. We're going to make this happen.’ So from there, I started more in earnest my career as it stands now.” 

Leadership Experience

After earning her Bachelor’s degree in Economics and Government, Kary became intrigued by the concept of business-building. This led her to become a management consultant. “It was a great way to explore the entire spectrum of the business world and learn how to analyze things. So, I worked at Deloitte for a little bit. But I knew very quickly that was not going to be the right path for me to go down.” Afterward, Kary worked for Uber in Mexico City, where she lived for a year and a half. She later moved to Chicago and earned her MBA at Northwestern University. 

After finishing school, Kary was contemplating her next move. She knew she had a passion for business and wanted to help build and grow something meaningful. During her time at Northwestern, Kary connected with Alpine Investors, who were seeking talented operators to infuse their businesses with new energy and drive growth.

Acquisition by ASG

“I was talking to Alpine, but I hadn't actually been officially deployed anywhere, if you will. So right after the sale, I talked to Alpine and they said, ‘Hey, we think you'd be a really good fit for this company. Let's start talking about it.’" Today, Kary is the CEO of Trucker Tools, which was bought by ASG, a portfolio company of Alpine Investors, in 2021.

The Start of Trucker Tools

The company, founded in 2009 and led by Prasad Gollapalli, was the OG mobile app for owner operators. “Prasad's background was from Get Loaded, which was a load board that was sold to DAT. So he knew the space and realized there was this huge gap in service for owner-operators who had this really difficult life out on the road. At the time, smartphones were just coming out. I literally had a flip phone in 2009. So that's how far ahead of the curve Prasad and our founding CTO Murali were, they saw this opportunity.”

Company Growth and Focus

A decade and a half later, the company has made a solid name for itself and has continued to expand its portfolio. “We're still really focused on just continuing to nail it and then expand. We're focused on brokerages and small carriers as our primary customers. We want to just keep focusing on adding value, solving problems when it comes to automating interactions. There's so much growth, especially on the carrier side, to continue to actually digitize these interactions.”

Mobile App Development

As for the mobile app? “We're making it a lot easier to integrate your ELD into our network. That's been a big focus of ours. We've got an amazing ELD team that’s adding thousands of integrations a month, but we can make that a lot faster and simpler through some of the mobile experience. Also, from a booking standpoint, making it easier for carriers to find good-fit loads for them.”

Leadership Advice

Kary also offered a golden nugget of wisdom for leaders who are joining a company. “You pay competitively. That is really important. You treat them really well. You don't come in and pretend like you have all the answers. You go to the people who actually know the stuff first, and you ask, ‘How do you recommend we do this? What are the problems here?’ And that's what I did in my first couple of months at Trucker Tools. I think you spend a lot of time talking and listening and asking good questions from the beginning, and then you start making small commitments and you deliver on them immediately.”

With a strong foundation and a clear vision for the future, Kary and her team at Trucker Tools are dedicated to making a lasting impact on the transportation industry, driving progress and creating value for their customers every step of the way.