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Journey Podcast

How Freight Sales Reps Win More Business by Asking Better Questions

Will Jenkins, founder and CEO of Journey, behind a chessboard.

Episode 96: Tom Curee, Ask Better Questions. Win More Business.

Released on
July 16, 2026

Tom Curee started in freight at 19, scheduling appointments and working with carriers at TQL. Twenty years later he's President of Qued, a company built to solve that same appointment scheduling problem at scale. In this episode he and Will Jenkins talk about what separates a trusted freight sales professional from someone chasing the next deal.

Tom's view is that sales starts with an honest answer to one question: can you help this buyer? Teams that try to sell every service end up forcing square pegs into round holes. He argues for picking the problems you understand best and becoming a specialist in them. Knowing when not to sell is part of the job, and the honesty earns referrals later.

The conversation also covers selling freight technology. An executive can approve a contract, but schedulers and operations teams decide whether the product gets used. Tom explains why trust with those end users matters, how appointment scheduling affects margins, and why the best sellers work on their customer's customer's problems.

Will and Tom close on discovery and style. Better questions uncover the real problem faster, and every rep has to find a selling style that fits who they are and learn to read the room. Reps who want to sharpen discovery can practice those conversations in the AI Sales Coach, and the Sales Bootcamp works on the same skills live with Will.

Episode FAQs
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