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Does Your Trucking Fleet Need a New TMS? [Video]

Cloud technology, AI and new integrations are changing what transportation management systems can do. But does taking advantage of those advances mean replacing your existing TMS?

Deborah Lockridge
Deborah LockridgeEditor and Associate Publisher
Read Deborah's Posts
November 5, 2026

Transportation management systems have come a long way. Today's trucking fleets have access to cloud-based technology, artificial intelligence, automation, and integrations that can connect everything from dispatch and driver communications to fuel purchases and billing.

But what if your existing TMS isn't getting the job done? Do you need to invest in an entirely new system to take advantage of those capabilities?

Not necessarily, says Bill Cain, director of product management for TMW.Suite at Trimble Transportation.

In this episode of HDT Talks Trucking, Cain joins Heavy Duty Trucking's Deborah Lockridge to discuss how fleets should approach TMS modernization — and why replacing an existing system isn't always the best answer.

They explore how newer technologies can work with established TMS platforms, what cloud-based systems really mean for trucking operations, and where AI may help fleets work more efficiently.

Watch the conversation to learn:

  • How to tell whether your current TMS needs an upgrade, new integrations or a complete replacement.
  • Why cloud-based technology doesn't necessarily mean abandoning an existing system.
  • How modern integrations can help fleets connect their TMS with other business and operational tools.
  • Where AI and automation are making inroads in dispatch, order entry, billing and other workflows.
  • What questions fleets should ask before making a major TMS investment.

The bottom line? Before shopping for a new TMS, take a closer look at what you need your technology to accomplish — and whether the system you already have can get you there.