Freight Broker Software / Trucking Software - Tailwind Pro TMS

Trucking and Freight Broker Software

You make the difference to your customers. It’s those little details you manage for your clients that sets you apart from others. It’s your knowledge and commitment to service that keeps your customers coming back.

Keeping your business data at hand, your trucking company or freight brokerage is ready to take on the challenges and responsibilities of multiple branches, rapid growth, and increased competition.

Tailwind Pro TMS Includes

Take your freight business to the next level with a cloud-based transportation management software that allows you to:

  • Run multiple branches and assign specific user access levels
  • Transmit quotes and orders directly - and have that data flow into QuickBooks Online
  • Turn expensive empty backhauls into fully loaded profits with key load board integrations

Tailwind TMS Pro also includes the POD Complete Mobile App - free for all your drivers. Never wait for (or lose) a POD again.

Take a quick, self-guided tour through the Tailwind TMS:

Key Benefits

tailwind pro tms

Work smarter and faster, with:

  • All key business data (dispatches, invoices, payments...) in one place, accessible anywhere
  • Auto-populating forms (no more duplicate data entry)
  • Ability to compete agains the big freight transport players - without the hefty price tag


  • POD Complete App - Free for all drivers
  • SMS Text Messaging
  • Load board integrations
  • Mileage calculations
  • Multi-branch management
  • Fuel bill importing
  • GPS Confirmed Shipment and Event Tracking (25 loads/month)



Tailwind Pro TMS is a cloud/web-based TMS - No Installation or Maintenance Fees required. You can get access to your system in under a minute of signing-up for a FREE trial.


Tailwind TMS has been specially designed to suit the needs of ground transportation companies across North America. As a cloud / web-based software, there are no setup fees or lengthy wait periods while software is installed or updated.

Designed for growing small to mid-sized ground transportation companies, Tailwind Pro TMS is best suited for:

  • Freight Brokerages
  • Trucking companies
  • Trucking companies that also broker, or brokerages with assets

Check out our customer case studies here or compare our TMS products to find the solution that's right for your transportation management business.

"Tailwind was able to check off several boxes - what really sold me was the customer service and ease of use. We opened a second branch and Tailwind was able to integrate seamlessly to get both of our branches to run simultaneously."

- David Segal Blouin, President, Depart Transport Inc

Evaluating On-Premise vs SaaS

On-Premise vs Saas Graph

Increase your savings. Check out Software Advice’s TCO (total cost of ownership) calculator. This calculator lets you analyze the cost for an on-premise software system vs a Software-as-a-Service (SaaS) system.

With our web-based TMS, you don’t need to perform any installations and you’re able to get up and running in a matter of minutes at your own convenience. This allows companies to save costs on hardware, additional software, and staffing, while providing the flexibility for access from anywhere.