Freight tech hype cycles come and go, but what actually sticks inside brokerages, carrier ops, and shipper TMS screens? The “Steve Jobs of freight,” Bill Driegert, traces the real arc of innovation in trucking – from American Backhaulers and the “Chicago model” to Uber-for-Freight experiments, digital freight matching, AI dispatchers, and the Convoy acquisition by DAT.

Bill has sat in almost every important seat in modern freight: early at Coyote, co-founder of Uber Freight, Head of Trucking at Flexport, part of the Convoy story, and now leading carrier products and strategy as EVP of Convoy Platform at DAT. He breaks down why each “epoch” of freight tech took a decade to matter, why pure-play digital brokers hit a ceiling, what the DAT + Convoy combo unlocks, and how AI, AVs, and scheduling will reshape the next 10–20 years.

What you’ll learn

• The real tech epochs in freight: From post-deregulation brokerage and the American Backhaulers / CH Robinson split, to broker TMS, to “Uber for freight,” to today’s AI and automation wave.
• Why “digital freight matching” stalled as a standalone model: The hard TAM limits of being “product pure,” and why the biggest brokers will build, while everyone else partners.
• Chicago vs cradle-to-grave brokerage models: How floor design, org structure, and TMS shape service, density, and which shippers you can actually win.
• Fragmentation, scale, and the future of brokers: Why tech makes midsize brokers more dangerous, why service still wins with SMB shippers, and why you shouldn’t bet on a winner-take-all market.
• AI’s real role in brokerage and dispatch: Where AI and “AI dispatchers” add value, where they just create more work, and why channel choice (app, TMS, email, phone) really matters.
• Autonomous trucks and carrier consolidation: How AVs could change capital requirements, operating models, and what a “carrier” even is – plus how brokers and 4PLs might evolve around them.
• Why scheduling is the final frontier: How appointment setting, facilities, and dock operations quietly cap automation – and why solving scheduling unlocks the next big efficiency leap.

Time-stamped highlights

• (00:00) Bill’s background across Coyote, Uber Freight, Flexport, Convoy, and DAT
• (05:00) Post-deregulation brokerage 101: CH Robinson vs American Backhaulers and the birth of the Chicago model
• (11:00) Building Coyote’s broker TMS and why V1 tech focused inside the four walls of the brokerage
• (16:00) Uber launches, “Uber for freight” is born, and why early apps were just mobile load boards
• (22:00) Convoy, Transfix, Uber Freight and the true end-to-end “app-first” operating model
• (27:00) Why pure digital brokers ran into TAM limits and why only the largest players can justify full-stack builds
• (33:00) What shippers actually care about: why transportation is often priority #5, not #1, in the C-suite
• (39:00) SMB vs enterprise shippers: how Landstar-type agents win locals while big RFPs reward scale and data
• (45:00) Fragmentation, minimum efficient scale, and whether broker consolidation really happens
• (51:00) AI in the wild: AI dispatchers, robocalls, and why every extra medium (phone, email, portal) is a process defect
• (57:00) How apps, TMS integrations, and “one-click” workflows beat phone calls for both carriers and brokers
• (1:02:00) AVs and the carrier of the future: capital intensity, new operator models, and deterministic dispatch
• (1:10:00) 4PLs and managed transportation in an AI/AV world: why the role changes but doesn’t disappear
• (1:16:00) Inside the DAT + Convoy + Truckers Tools + Outgo stack: what Bill’s building for carriers and brokers now
• (1:22:00) Scheduling as the under-loved bottleneck: why docks, facilities, and appointments still block automation

Guest

Bill Driegert — EVP of Convoy Platform, DAT Freight & Analytics
Bill has been at the center of nearly every major freight-tech wave of the past 15 years. He was an early employee at Coyote Logistics, co-founded Uber Freight, led trucking at Flexport, and now guides carrier strategy and product at DAT following the acquisition of Convoy’s technology.
LinkedIn: https://www.linkedin.com/in/driegert/

Links & references

• DAT Freight & Analytics: Load boards, rates, and network intelligence for brokers, carriers, and shippers — https://www.dat.com/
• Convoy (acquired technology by DAT): Background on the digital brokerage and platform Bill helped integrate
• Uber Freight: Digital brokerage and 4PL / managed transportation offering — https://www.uberfreight.com/
• Coyote Logistics: Large brokerage built on the “Chicago model” Bill joined as an early employee

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