McLeod Software: The Software Behind 1,200 Trucking Companies | Tom McLeod on Behind The Wheelhouse

In this episode of Behind the Wheelhouse on Trucker Talk Radio, Tom McLeod, founder, president, and CEO of McLeod Software, joins Jon and Justin for a wide-ranging conversation about 40 years of building the technology infrastructure that powers over 1,200 trucking and freight brokerage companies across North America. Tom traces the company's origins back to 1985, when deregulation opened the floodgates for new carriers and almost nobody was building software to help them run. With a background in classical piano and sales, he made a calculated bet on an industry big enough to sustain a growing company but niche enough to stay off the radar of IBM and Microsoft.Tom walks through how the industry has evolved from 80-megabyte hard drives and isolated green-screen terminals to fully integrated TMS platforms with 150 integration partners handling everything from order entry and freight billing to driver payroll, fuel tax, and real-time GPS visibility. He explains why integration is not optional anymore, why technology for technology's sake often creates more manual work than it eliminates, and why the companies that invest in the right tools tend to be better-managed companies across the board.The conversation dives into the recent Supreme Court ruling removing federal liability shields for freight brokers, and what it means for carrier vetting and driver verification going forward. Tom sees it as a net positive for the industry, arguing that overcapacity driven by underqualified drivers has suppressed rates for years and that raising the bar on safety standards benefits carriers, brokers, and shippers alike. He also shares what McLeod is doing with AI right now, from automating load entry and rate quoting to accelerating internal development cycles.On autonomous trucks, Tom offers a grounded take: it is coming, but slower than anyone predicted, and the disruption it creates will open new opportunities for carriers who are prepared. He predicts that by 2035, between 10 and 15 percent of miles traveled could be autonomous, and believes the transition will ultimately give drivers better lives with more regional routes and more time at home. His closing message is simple: disruption creates opportunity, and the carriers who lean into new technology will be the ones still standing.Chapters0:00 Intro1:30 Starting McLeod Software in 19853:13 What Early Trucking Software Looked Like4:44 Green Screens and Early Computers6:34 How Tom Got Into Software8:18 Supreme Court Ruling on Broker Liability11:21 How the Ruling Shapes Software Development13:49 How Technology Changed Trucking Operations15:57 Driver Verification and ReadyApp18:26 The Importance of Integration Partners21:20 Longest-Running McLeod Customers22:54 AI at McLeod Software25:31 Autonomous Trucks and the Future30:02 What Autonomy Means for Drivers32:18 What Still Motivates Tom After 40 Years33:04 Why Smaller Carriers Should Consider McLeod35:34 What McLeod Is Building Next36:50 Sponsor Messages and OutroFollow Us!X: https://x.com/trucktalkradioIG: https://instagram.com/truckertalkradioTikTok: https://tiktok.com/@TikTok: https://tiktok.com/@truckertalkradioFollow Tom McLeodLinkedIn: https://www.linkedin.com/in/tom-mcleod-8466b0https://www.linkedin.com/company/mcleodsoftware/Website: https://www.mcleodsoftware.comPowered by Ready AppThe driver-verification platform protecting brokers, carriers, and shippers from identity fraud, onboarding risks, and unsafe hires.Learn more at: https://ready-app.comSupport GreyCross.orgA 501(c)(3) supporting families affected by roadway tragedies across America.Donate at: https://greycross.org#truckertalkradio #behindthewheelhouse #mcleodsoftware #truckingtech #tms #freighttechnology #truckingpodcast #autonomoustrucks #ailogistics #freightbroker #owneroperator #truckinglife #supplychain #logistics #cdldriver #truckdriver #freightindustry #truckingindustry