Most carriers spend weeks on TMS demos and minutes on the contract. That asymmetry is how fleets end up locked into a 3-year deal with no data export, surprise integration fees, and a roadmap that never ships. The 6 questions below are the ones that surface every issue before the signature, and the ones the best vendors will answer in writing.

1. Do we own our data, and how do we get it out?

Your loads, drivers, settlements, invoices, factoring history, and IFTA records are the most valuable asset you create on a TMS. The contract should answer three things in writing.

• You own the data, the vendor stores it

• You can export the full dataset in a standard format on demand

• You get an export window after termination, with a stated number of days

If the contract says "data is the property of [Vendor]" or "export available upon written request," walk. A data migration flow that imports cleanly is the same flow that exports cleanly, and a vendor confident in their product makes both easy.

2. What is bundled, what is an add-on, and what is the price for each?

"All-in-one TMS" usually means "all-in-one if you pay for all the add-ons." Ask for a price sheet with every module the demo showed, broken into base and add-on.

Datatruck pricing is tiered by truck count, not per user or per load. Get the same clarity from any vendor you are evaluating, see the live numbers on datatruck.io/pricing.

3. What does the AI actually do, and how was it built?

"AI-powered" is the most overused phrase in TMS marketing. The right follow-up is a feature-by-feature breakdown. For Datatruck the AI surface is four products that ship weekly.

• TruckGPT reads rate confirmations in under 15 seconds at 90 percent-plus accuracy

• AI Dispatcher works DAT, Truckstop, 123LoadBoard, Uber Freight, RXO, and 100-plus private boards

• AI Updater drafts broker emails and triggers geofenced driver check-ins

• BI Agent answers profit-per-truck questions in plain English

If the vendor cannot name the AI product, describe what it does, and show it running on real data in the demo, the AI is marketing copy. AI-native platforms behave differently from legacy TMS with an AI feature bolted on.

4. How do you handle migration, and how long does it take?

The migration plan should be in writing before the contract is signed. Ask for the named steps, the duration of each, and the data sources the vendor has migrated from before.

1. Discovery and source-system audit

2. Master records: drivers, trucks, customers, brokers, chart of accounts

3. Historical load and settlement import (12 to 24 months)

4. Parallel run on at least one workflow

5. Cutover date in writing

6. Post-cutover support window

Carriers who skip step 3 are the same carriers whose migrations stall in week 2. Datatruck has run 300-plus migrations with 99.9 percent data accuracy and zero downtime.

5. What integrations are included, and how are new ones handled?

The TMS sits at the center of a stack: ELD, telematics, fuel, tolls, factoring, accounting, load boards, CRM. Ask for the current integration list, the cost of any extra integration, and the SLA for adding a new one.

Datatruck ships 100-plus integrations on the apps marketplace with per-partner setup articles. EDI is a flat $499 per connection. New integrations are added on a weekly release cadence, not on a 6-month roadmap promise.

6. What is the release cadence, and where can I see what shipped last month?

A TMS is software, not a static product. Vendors who ship monthly compound capability fast. Vendors who ship quarterly fall behind the AI curve in a year.

Ask for the changelog or release notes for the last 3 months. Datatruck publishes product updates on a weekly cadence with the AWS-native infrastructure to back it. If the vendor cannot show you the last 3 release posts, the cadence is slower than the marketing claims.

Three contract clauses worth pushing on

Beyond the 6 questions, three clauses are worth negotiating before signature.

• Auto-renewal language. Should require explicit re-signature or a 30-day notice window, not silent rollover for another year

• Uptime SLA. AWS-native vendors should be willing to commit to 99.9 percent or better, with credits for breach

• Data export at termination. Should be a stated window in days, not "upon request"

None of these are unusual asks. Vendors confident in their product agree to all three.

What the demo should actually prove

Walk into the demo with a copy of one of your own rate confirmations, one of your own settlement runs, and one of your own broker emails. If the AI cannot handle your real documents on the spot, the AI is a marketing demo, not a production system. Datatruck's self-serve demo account is pre-populated with realistic data so you can test the workflow before a sales call.

If the answers to these 6 questions, and the demo on your own data, hold up, the contract is the easy part. Book a walkthrough to run the questions live against Datatruck.

FAQs

What should I ask before signing a TMS contract?

Six questions cover most risk: data ownership, bundled vs add-on pricing, AI specifics, migration plan, integration list, and release cadence. Each should be answered in writing before signature, and the AI question should be backed by a demo on your own documents.

How long should a TMS contract be?

One year is the sweet spot for mid-sized carriers. Three-year contracts only make sense if the pricing discount is meaningful and the data-export and termination clauses are tight. Avoid auto-renewal language without a 30-day notice window.

What does TMS pricing usually include?

Base plans usually include dispatch, settlements, basic reporting, and a fixed number of users or trucks. Add-ons commonly cover AI features, advanced reporting, EDI, and premium support. Ask for a price sheet with every module separated.

How do I evaluate AI features in a TMS?

Ask for named products, a specific outcome per product, and a demo running on your own rate confirmations and emails. If the vendor cannot name the AI product or run your real data in the demo, the AI is marketing copy rather than production capability.

Book a Datatruck demo