TMS RFP Playbook: How to Run a Transport Management Software Selection That Gives You a Decision

Every vendor says yes to everything. The RFP is where you find out who can back it up.

A transport management system (TMS) is software you'll run for years and can't easily swap out. But by the time the demos start, the decision is mostly made. It comes down to the requirements you write and the questions you ask. A vague RFP can't separate one vendor from the next, so proposals come back looking the same and you will end up deciding purely on price.

This is a practical, step-by-step guide to running a TMS RFP that actually reaches a decision. It's written for the procurement, operations, and logistics managers at shippers like manufacturers and wholesalers who are choosing a transport management system and want a process they can defend.

Inside, you'll learn how to:

• Decide whether you even need an RFP, or whether a few demos will serve you better
• Write requirements so that vendors answer honestly, instead of ticking "yes" to everything
• Provide the operational context that makes TMS proposals comparable
• Model the real three-year cost of ownership, not just the monthly subscription
• Evaluate proposals on carrier connectivity, integration, and fit, not price alone
• Run demos that test the actual system against your real scenarios
• Handle the contract, SOW, and onboarding while you still have leverage

The book includes five ready-to-use templates: an RFP document, a functional requirements scoring sheet, an operational information checklist, a vendor evaluation matrix, and an RFP timeline.

Written by Ülari Kalamees, co-founder and CEO of Cargoson and former COO of DSV Estonia, who has sat on both sides of the RFP and answers buyers' requirements almost every week. This is the guide he wishes buyers had in front of them before they started writing.