Tailwind Pricing, Features, Reviews & Comparison of Alternatives


Web-based trucking & freight broker software for SMBs

4.52/5 (46 reviews)

Tailwind overview

Tailwind is a true web-based trucking and freight broker software, catering to small and mid-sized trucking businesses, freight brokerages, and businesses that do both. There are no up-front fees associated with this Transportation Management System (TMS), and you can start with a free trial.

Tailwind is offered in three-tiers. Tailwind Standard costs $69 user/month, Tailwind Pro - $99 user/month and Tailwind Enterprise - $139 user/month. Each level includes integration with QuickBooks Online, and a free mobile ePOD capture and dispatch communications app (Tailwind POD Complete) for all drivers associated with a business' subscription.

Tailwind Standard is the basic package suitable for a small business; offering features such as operations and accounting, sales tracking , carrier rate history maintenance and more.

Tailwind Pro is an extension to this basic plan and supports multi-offices and multi-division businesses. It allows clients to track mileage, claims, incidents and accidents. Clients can also access multiple load boards and post their freight or equipment to get new customers and orders.

Tailwind Enterprise is the premium offering which supports integration with various third-party transportation services and includes additional features such as Customer and Carrier Portals which give companies the ability to provide more self-serve options for their customers and partners.


Starting from
Pricing options
Value for money
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Business size



United States, Canada

Supported languages

Tailwind screenshot: Tailwind login screenTailwind Trucking and Freight Broker SoftwareTailwind screenshot: In-app tutorials and live chat support get you up and running quicklyTailwind screenshot: Easily create and manage customer recordsTailwind screenshot: Dispatch and track all your shipmentsTailwind screenshot: The free Tailwind POD Complete mobile app lets drivers capture signed BOLs and electronic signatures upon delivery so they can send in PODs immediately for invoicing. Drivers can also send in arrival and departure times directly into the home TMS. Tailwind screenshot: Manage drivers and personnelTailwind screenshot: Set task alertsTailwind screenshot: Create, manage and post invoices out of TailwindTailwind screenshot: Post equipment to load boardsTailwind screenshot: Keep track of equipment and service recordsTailwind screenshot: Easily manage your receivables

Tailwind reviews

Value for money
Ease of use
Customer support
Jason Dembow

An awesome program that is a life saver for small freight brokerages!

Used daily for 1-2 years
Reviewed 2018-03-27
Review Source: Capterra

The software is awesome. It makes my life easier on a daily basis. Out of the many TMS softwares I reviewed, this one has almost every feature I was looking for and has an extremely affordable price.

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Pamela Leclerc

Tailwind is great!

Used daily for 2+ years
Reviewed 2016-06-20
Review Source: Capterra

Our initial experience with Tailwind was a little "rough". However, John and Kyle worked with us and saw us through our implementation problems. What I really like about Tailwind is the support. The support team is responsive and appropriately reactive. With respect to the program, it is organized and user friendly. We broker in our business and had tried some demos with other transportation management systems but they didn't fit as well as Tailwind has. Tailwind makes our work more efficient, there are fewer mistakes made as you only have to enter the data once and we can see the process through to billing. Tailwind has helped our business to grow and become more profitable.

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John Sternig

Tailwinds rating review

Used daily for 1-2 years
Reviewed 2016-06-17
Review Source: Capterra

We started with Tailwinds in 2013 and found that the software developed our internal system to where we could increase both dispatchers and accounting efficiencies. Working together with Tailwinds, we've increased our business significantly without any development problems with the volume increase.

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Larry Fowell

Tailwinds is my office support staff

Used daily for 2+ years
Reviewed 2018-12-06
Review Source: Capterra

My company has made great advances because the software allowed me to have good record keeping and dispatches with information not having all the extra paperwork in files but only the backups. Efficiency of what this has allowed me to do by giving me the time. can do the work of 3 people

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Daniel Torres

Tailwind Review

Used daily for 6-12 months
Reviewed 2019-01-21
Review Source: Capterra

great TMS , it can handle my loads very easy, is the only software that I know , than can handle an international load, taking a mexican carrier, with their own trailer number, involve a wharehouse , transload the product to a US carrier with a different trailer number , and give you the avaibility to track the load in one single order, not just that, it also provide indivual instructions and BL for each party, and receive the invoice for each carry involve so payments for each of them can be done with the proper administration, and for you customer can get togther all this job and send them just one invoice for the all service... this TMS is great

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Tailwind pricing

Starting from
Pricing options
Free trial
View Pricing Plans

Tailwind Standard: $69/user/month - Free Trial
Tailwind Pro: $99/user/month - Free Trial
Tailwind Enterprise: $139/user/month

Tailwind features

Data Import/Export
Order Management
Route Management
Third Party Integration

Activity Dashboard (32 other apps)
Automated Scheduling (23 other apps)
Automatic Notifications (28 other apps)
Delivery Tracking (36 other apps)
Email Notifications (24 other apps)
GPS (26 other apps)
Geographic Maps (25 other apps)
Location Tracking (25 other apps)
Real Time Data (29 other apps)
Real Time Monitoring (29 other apps)
Real Time Updates (29 other apps)
Reporting & Statistics (39 other apps)
Route Optimization (26 other apps)
Shipping Management (38 other apps)
Status Tracking (28 other apps)

Additional information for Tailwind

Key features of Tailwind

  • IFTA mileage calculation & tracking
  • QuickBooks Online integration
  • Tailwind POD Complete Mobile App
  • Customer Portal - give customers access to shipment status
  • Carrier Portal - allow carriers to see available loads & pay
  • Accounts receivable & payable management
  • Self Serve Customer and Carrier portals
  • Automated commission management
  • Customer and vendor database
  • Quick templates for order and quotes
  • Customer Record imports + POD import tool
  • Customer & carrier rate history
  • Customer rate tables
  • Complete quote & order system
  • Dispatch & shipment tracking system
  • QuickBooks Online
  • Customizable quotes
  • Task & alert notification system
  • Integrate with QuickBooks
  • Claims/incidents/accident tracking
  • Fuel bill importing
  • Equipment maintenance tracking
  • Locations and route management
View All Features


• Tailwind is a web based product and can be accessed from any device, at any time.

• The solution integrates with various key technologies in the trucking industry such as load boards, mileage, IFTA, accounting and fuel supply.

• The Tailwind TMS allows your business to transmit, fax, email, and scan documents from the same solution.

• The product is integrated with Here.com, PC Miler and ProMiles for route and load optimization.

• With Tailwind's web tracking module, clients can post their freight brokerage on multiple load boards such as Post Everywhere, DAT Solutions, Truckstop.com, and can connect with new customers.