Step into the world of innovation and excellence with “Industry Champions”! Join us as we celebrate the trailblazers who are redefining success across diverse industries, sharing their journeys, strategies, and secrets to thriving in competitive landscapes. Today our host, Tom Reber, spoke with Connor Miller.
Connor Miller
CEO at FreightScout
Website Address: https://freightscout.ai/
Short company description:
FreightScout is the AI operating system for freight brokerages — a $900B industry still run on phone calls, spreadsheets, and 1990s software. The platform deploys AI agents that automate the operations floor: making carrier check calls, building loads, catching margin leakage, and turning every conversation into structured intelligence.
What was the biggest obstacle you had to overcome in your business?
Deciding to build a technology platform when I barely have a high school diploma. I’m not a trained engineer. I spent twelve years on freight brokerage operations floors, not in computer science classes. So the biggest obstacle was getting past the voice that said you’re not the guy who builds software like this. What I had instead was twelve years of knowing exactly what was broken and why — and it turned out that knowing the problem cold mattered more than the credential. I taught myself what I needed to build it, and now there’s a real platform running live operations at a brokerage. The lesson I’d give anyone is that domain expertise plus the willingness to figure it out beats a resume.
What are your company’s strengths?
Our biggest strength is that it’s built by someone who lived the problem. I spent twelve years in freight brokerage operations and helped scale a brokerage from $15M to $130M, so every feature solves something I personally dealt with — a missed check call, a billing hold nobody owned, knowledge walking out the door when a rep quit. The second strength is that it’s real and in production today, not a concept. We’re running live operations at a brokerage with AI agents handling carrier calls and load building, with an enterprise pilot underway at a $2B company. And the operational data we collect compounds every day in a way a competitor starting now can’t go back and replicate.
Who in the industry inspires you and why?
Jeff Silver. He built Coyote Logistics into a billion-dollar brokerage and sold it to UPS, then instead of retiring he went back and started Mastery to build the modern TMS the industry actually needed. What inspires me isn’t just the outcomes, it’s that he’s spent four decades solving the same hard problem from every angle — as a broker matching loads by hand, as the operator who scaled a company on culture and a ‘no excuses’ standard, and now as the technologist rebuilding the infrastructure underneath the whole industry. He proved you can come from inside freight operations and still build category-defining technology. That’s the exact path I’m on, and he set the standard for it.
What is the most enjoyable part of what you do?
The most enjoyable part is the moment something I built actually takes work off a real person’s plate. When an operations manager walks in Monday morning and the system already tells them which loads are at risk and which carriers went dark over the weekend — work that used to eat their whole morning — that’s the payoff. I spent years doing that job by hand. Building the thing that does it automatically, and watching it work for the people still in the trenches, is the part I love.
