The challenges of scaling a startup in the rapidly-changing freight industry

“I’ve had to be very adaptable. I realized that I needed to focus on the things I’m in control of. As an entrepreneur, you stink at a lot of things in the early days,” smiles Josh Keller, “but hopefully I stink at fewer things now.”

Keller (BComm ‘13) knows a thing or two about adaptability. As Co-founder and Director of Partnerships for FleetOps (external link) , he spends his days as the non-technical point of contact for client success. FleetOps is a B2B logistics technology company operating a freight marketplace that uses ELD data to match trucking companies with shipping opportunities. 

“Most people are not familiar with the freight industry, and I wasn’t until I came into trucking, but you could almost consider it like a dating app with drivers and trucking companies on one end, and brokers and shippers on the other,” explains Keller. 

Key to FleetOps’ operation is an ELD (external link) , a mandated piece of hardware connected to the truck's engine control module. “It’s the difference between FleetOps and a traditional load board. “Let’s say a broker needs something moved, they will post it on something called a load board (external link)  that the driver can search for. An ELD logs the amount of time truckers spend on the road, making sure they are compliant,” says Keller. “We have an algorithm that matches freight in our system with carriers, so they don’t have to search. 

“We help make sure the right people are talking to each other on both sides, but in a way that brings some efficiency into the industry.”

FleetOps was not Keller’s first foray into the freight industry; he had a similar role as Co-Founder of FleetRover (external link) , an earlier fleet tracking intelligence company. “FleetRover was pre-ELD mandate,” says Keller, describing the federal mandate that went into effect late 2017 in the United States and 2021 in Canada. “It was an ELD division we came up with in partnership with a trucking company, and the intention was to capture a lot of market share.” 

Within a year, FleetRover was in talks to pivot. The mandates saw a commodified market saturated with small ELD providers and a few large companies with hundreds of thousands of drivers. “It was a challenge we faced early on. You couldn’t sell more ELDs really easily without stealing market share from other providers, and that means your customers are being siphoned off as well.”

“We wouldn’t be in this space without our original partner who did the [ELD] hardware,” admits Keller. “It was also critical to us that our customers had notice to transfer to another ELD. Part of the responsibility we took on is delivering bad news to a partner or client. As a co-founder, I truly believe that the matching marketplace of FleetOps was the future of our business. We could have focused on running an ELD division but we would have never gotten to the scale of these larger companies.

FleetOps was part of the DMZ, one of the top-ranked startup incubators in the world, from 2017-2019. Having first learned about the space as a student attending Toronto Metropolitan University (formerly Ryerson University), Keller was keen on leveraging the DMZ to grow his new venture. 

“It would be 7:30 PM on a Friday, stepping out in the middle of downtown seeing everyone going outside to bars and movies, but you and a bunch of other entrepreneurs are just exhausted because we’re all trying to do something different—community was huge at the DMZ,” he says. “Not only was it this trendy place with coffee machines, but there was the ability to cross-pollinate ideas with other entrepreneurs.”

“There was programming that helped FleetOps as well. When we needed legal advice, we would book time with the legal team, or with the marketing team if we needed sales support,” adds Keller. “When you’re a small startup facing challenges, bootstrapping and scrimping your way to make it happen—all the assistance is critical, and we’re very appreciative of the DMZ’s help.” 

The DMZ is where Keller’s partner and FleetOps Co-Founder Chris Atkinson met Ted Rogers School of Management alum Justin Sky, CEO and Co-Founder of Rose Rocket, a transportation management software (TMS) company. “We partner with them instead of trying to make a relationship with 18,000 different brokers. I manage that one-on-one TMS relationship since a lot of users don’t have their own technical infrastructure,” he says.

FleetOps has grown from four desks at the DMZ to a team of nearly 40 people, with employees ranging from Toronto and Chicago, to countries like Brazil and India. Moving forward, Keller is set on building out his employees’ capabilities. 

We’re constantly focusing on delivering value to our stakeholders,” explains Keller. “As an employer, we are the reason that people have a livelihood, which is amazing to me. I spend a lot of time externally focused on partners, but I also firmly believe in having a solid foundation for our staff.”

“If I can teach them lessons I learned from the early days, the support, knowledge, training and tools they need to be incredible employees will be there,” says Keller. “If we can do that, we’ll have a loyal team. Their ability to be happy and successful only benefits us, in the long run.”