Start with how your business actually works
Most TMS shortlists start with a feature list. A better starting point is a plain description of how freight actually moves through your business today — which service lines you run, where the handoffs are, and where staff currently work around the system rather than with it. That description becomes the test every shortlisted product has to pass.
Map your service lines before you map features
General freight, container cartage, and specialised freight each carry their own operational rhythm. General freight is driven by multi-drop runs and delivery windows. Container work is driven by VBS slots, free days, and dehire deadlines. Specialised freight often carries its own compliance and equipment requirements. A TMS built primarily for one service line will usually make the others feel bolted on, so ask vendors directly how each service line is actually modelled in their system, not just whether it's supported.
Check whether one rate engine can handle all your freight types
Billing complexity is where multi-service operators feel the pain first. If general freight, container, and specialised work each need their own workaround to get an accurate rate card applied, your finance team will end up doing in spreadsheets what the software should be doing automatically. Ask to see a rate card built for a customer who receives more than one service type, and ask how surcharges and accessorials are captured differently across them.
Test how dispatch handles a mixed fleet in a single day
A dispatcher planning a day that includes multi-drop curtainsider runs, container moves against VBS slots, and a specialised job shouldn't need three separate screens to do it. During a demo, ask to see a single dispatch board that shows all three job types side by side, with driver hours and vehicle capacity visible across the whole fleet — not filtered to one service line at a time.
Weigh integration needs against what you already run
Few operators are starting from a blank slate. You likely already have accounting software, telematics, and possibly port or rail system connections in place. Be specific with vendors about which of these need to exchange data automatically versus which can be handled with occasional manual export — the honest answer affects both cost and timeline, and a vendor who claims every integration is trivial is worth double-checking.
Involve the people who will use it daily
Dispatchers, drivers, and billing staff will notice friction in a new system faster than anyone evaluating it from a spreadsheet of features. Where possible, get a dispatcher to plan a real day's mixed-fleet workload in a trial environment, and get a driver to run through job capture and POD on their own phone, before you commit.
A short checklist before you sign
Before signing, confirm four things in writing: how each of your service lines is handled end to end, how rate cards work across freight types, which integrations are included versus custom, and what implementation and data migration support is provided. A vendor who can answer all four clearly, with examples from your own service mix, is a much safer bet than one who answers in generalities.