Ep. #82: Alan Holland, Founder & CEO, Keelvar

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Mar 25, 2026

Alan Holland, founder and CEO of Keelvar and former AI researcher, explains how auctions, sourcing optimization, and AI agents can reshape freight buying. He discusses package bids that let small fleets win, incentive-compatible auctions that surface true preferences, Google Ads as an auction model for procurement, and a future of agent-run bidding and multi-shipper combinatorial exchanges.

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ANECDOTE

AI Researcher Who Lived Freight Pain

Alan Holland watched AI research by day and helped his family's chemical business by night, which exposed him to freight pain points firsthand.
He combined e-commerce auction work (Google, Amazon) with B2B freight realities to start Keelvar and scratch that operational itch.

INSIGHT

Incentive Compatible Auctions Reveal Truth

Mechanism design matters: buyers set the rules so auctions should be incentive compatible to surface truthful supplier preferences.
Google succeeded not just by search quality but by charging second-price and ranking on bid × quality to reward relevant, reliable advertisers.

ADVICE

Connect Sourcing To TMS Performance

Do integrate operational performance into sourcing so price and execution quality are jointly optimized and good carriers get rewarded.
Connect sourcing to TMS on-time metrics and weight service heavily when perishable or in-stock risk exists.

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Freight buying has a dirty secret: most bids do a great job of finding the lowest number and a terrible job of finding the best outcome. When shippers reward price without measuring service, good carriers get punished, bad actors slip through, and procurement teams spend weeks in spreadsheets trying to guess what suppliers actually want.

We sit down with Alan Holland from Keelvar to break down a better approach using sourcing optimization, mechanism design, and AI agents. Alan explains how incentive compatible auctions can pull truthful preferences to the surface, why package bids and conditional discounts create space for small fleets to win the lanes they can run best, and how the Google Ads auction is a surprisingly useful model for modern freight procurement. From there we get practical: connecting transportation management system performance data to the sourcing event, weighting on-time performance with price, and designing feedback loops that reward reliable execution instead of “cheap and shaky” promises.

We also zoom out to the bigger AI shift. Massive compute, LLMs, and code generation tools like Claude Code are changing how software gets built, which means logistics technology will evolve faster than most teams are ready for. We talk about risk, uncertainty, penalty cliffs, rebate targets, and the long-term “holy grail” of multi-shipper combinatorial exchanges that could unlock network-level efficiency.

If you care about freight procurement strategy, logistics automation, AI in supply chain, or the future of brokers and carriers, hit play. Subscribe, share this with a friend in logistics, and leave a review with your biggest question about where AI agents help most.

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