🎣 The #1 Problem
Plus: Automation scales from highways to rail, brokers face heat over illegal CDLs, ATA rethinks the “driver shortage,” and more in today’s newsletter.
We sat down with the founders of Vooma to talk about AI– and how their platform is helping brokers and carriers spend their time on more meaningful work.
In 2022, the two Stanford alumni, Jesse and Mike, were introduced by a mutual friend.
Jesse was exploring an idea with self-driving, and Mike was working on the last-mile space and in-delivery van robotics. The two connected over an idea that would spark an AI platform that reimagined logistics.
“A mutual friend thought we should meet — and they were right."
Jesse, who spent years working as a freight tech CEO and CRO of Trucker Tools, and Mike, who worked on self-driving trucks at Uber and Kodiak, saw firsthand how the work that drives growth was limited by operational capacity.
In 2022, they began exploring a vision of building a universal broker/dispatcher for the trucking industry.
The company officially launched in 2023.
Since then, they have automated millions of loads for brokerages, from Axle Logistics to WWEX, Sunset Transportation, and more. Jesse recalled the moment they knew they were onto something.
“We got our first ‘aha’ moment when a few early mockups on Figma led to signed contracts. That’s when we knew we were solving a painful problem people were willing to pay for.”
Fast-forward to today: Vooma has evolved into a full orchestration platform — from quote to cash — enabling logistics teams to build AI workers that handle repetitive work, such as quoting, covering, scheduling, and building loads.

Their goal?
“The biggest unlock is this sense of relief and freedom for people to be able to focus on the stuff that is really important but isn’t in the non-urgent bucket."
Jesse and Mike's aim was to meet users where they are in their workflows.
Along the way, they found one key challenge: teaching AI the nuances of freight- all the little details that only experienced brokers know. So what is the solution?
“AI doesn’t need to get smarter to transform logistics; it needs better data and context.”
Winning Trust in a Tech-Averse Industry
While we can see more and more companies implementing elements of AI, a big percentage is still tech-averse.
Convincing teams that AI is a ‘when’, and not an 'if', means helping them work more efficiently, even if they're a little cautious about new technology.
“When folks implement the quoting tool, one of the challenges is that there’s a lot of employee turnover in this industry, naturally. What we’re seeing is folks are getting a lot of consistency and are starting to build that knowledge in so that they’re creating more resilient businesses.”
Adopters are seeing the impact: Whitewater Freight cut new rep training from weeks to days, while Sunset Transportation saw 66% faster response times and Direct Traffic Solutions jumped from 39% to 100% call coverage.
So how do they convince people that Vooma can transform the way they work?
“I think we’ve done a good job of building strong relationships and delivering for our customers, and I think that’s a big piece of it. What we’re seeing people looking to partner with somebody that will be able to help them with a transformation over the long term. I think what we’re really good at is showing up for our customers and showing them that there’s a roadmap that we can help them move through,” says Jesse.
To those still weary of AI, the time has come to realize how far its capabilities can reach and change their company- for the better.
“Some companies realize that this is a really critical capability, while others see it more as just an afterthought. It’s just really important to get really good at this muscle of being able to implement and realize the return that you expect around technology- that’s what separates the very best of their customers from the ones that really struggle a little bit.”
The Future of Freight
While the future of the world remains a mystery, one thing is for certain- AI isn’t going anywhere. Jesse predicts that within a couple of years, the shift of humans communicating across freight is going to be dramatically lower than it is today.
“There will be AI that represents all of the stakeholders in the ecosystem- both brokers and carriers, shippers– and AI is going to be handling a lot of that communication. I think that it could actually happen a lot faster.”
Vooma’s story is a testament that innovation doesn’t always mean replacing people — it means empowering them. By combining human expertise with smarter data and thoughtful AI, they’re not just changing how freight moves — they’re redefining what’s possible in logistics.
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