Detailer's Leap
Dustin Jackson, Mike Karlen, Davy Tyburski

How to Run a Transport Management Software Selection That Gives You a Decision
Ülari Kalamees · Jan 1, 2026 · eng
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A practical guide to running a transport management software (TMS) request for proposal that reaches a defensible decision. Written for the procurement, logistics, and operations managers at manufacturers and wholesalers who run these selections. The author, [Ülari Kalamees](https://www.linkedin.com/in/ularikalamees/), is co-founder and CEO of [Cargoson](https://www.cargoson.com/), a transport management software company, and writes from the vendor side of the process: the book is drawn from the RFPs his team answers each week. It covers whether an RFP is needed at all, the nine-step process, the operational context vendors need to quote accurately, prioritised functional requirements, three-year cost modelling, evaluation beyond price, and contract and implementation. Includes five ready-to-use templates: an RFP document, a functional requirements scoring sheet, an operational information checklist, a vendor evaluation matrix, and a timeline plan.
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