Tailwind Fleet Management

14 Reviews 4.5/5

A fleet maintenance software offering automated BOLs and load and cost management.

Product Overview

Tailwind is a fleet management software. Key features include automated BOLs, effective load and cost management, and responsive customer support. Its affordability and tailored features make it a good fit for smaller operations seeking to improve efficiency without the need for complex or expensive software​​.


  • Responsive customer service
  • Free trial available
  • Effective booking, costing of loads, credit management


  • No free version
  • Some functionality lost in version updates
  • Limited customization options

Target Market

Small to mid-sized logistics and transportation businesses, including freight brokerages and trucking companies.

About Tailwind

Tailwind is an all-in-one transportation management software that has all the features needed by freight brokerage, carrier, moving and storage, and freight forwarding companies. It helps small to midsize trucking companies and freight brokerages organize their business to improve profitability.

Tailwind Features

The features of Tailwind include:


  • Customer and Vendor Database
  • Complete Quote & Order System
  • Customer & Carrier Rate History
  • Equipment Maintenance Tracking
  • Claims/Incidents/Accident Tracking
  • Dispatch & Shipment Tracking System
  • Locations and Route Management
  • Task & Alert Notification System
  • Accounts Receivable Management
  • Accounts Payable Management
  • Driver/Carrier Settlements
  • Sales Commission System
  • Email Documents with Company Logo
  • Pre-configured Admin, Accounting & Operations Reports


All features from Standard version, plus:

  • POD Complete Mobile App
  • SMS Text Messaging
  • Load Board Integrations
  • MacroPoint Integration
  • Mileage Calculations
  • Fuel Bill Importing
  • Multi-Branch Management
  • Custom User Security
  • POD Import and Attach
  • IFTA Mileage Tracking
  • QuickBooks Online Sync


All features from Pro version, plus:

  • Customer Self-Service Portal
  • Carrier Self-Service Portal
  • Electronic Load / Rate Confirmation & Acceptance
  • Trucker Tools Smart Capacity Integration

Industries Served

Tailwind is best used by companies dealing in:

Freight Brokerage

Introducing freight brokerage management software for companies, both large and small businesses. Tailwind allows businesses to manage multiple locations with one software system. The platform can also automate quote acceptance for brokerages and 3PLs.

Carrier & Trucking

Tailwind’s carrier management dispatch software is easy to use and manages all aspects of Truck Load (TL) / Less than Truck Load (LTL), Dispatch, Sales, Fleet Management, Accounts Receivable (A/R), Accounts Payable (A/P), Operations & Administration.

Moving & Storage

Moving software application that enables moving and storage companies to simplify processes, reduce costs, increase revenues, and improve customer loyalty.

Freight Forwarding

Tailwind provides moving and storage software that enables companies to simplify processes, reduce costs, increase revenues, and improve customer loyalty.

Tailwind Pricing

The cost of Tailwind starts at $99/user/month, billed annually. There is a free trial available. There is no free version available.

Video Overview

Starting Price
$99 /user/month
Price Range Learn More
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Product Overview

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User Reviews of Tailwind

Submitted on March 15th, 2023 by Richard Prescott

We ended up going with Tailwind for our TMS system. We liked the program becasuse everything is in one place. All the features we need are right in front of us and within a hands reach. Their support has been good so far.

The Good…

Everything in one place

The Bad…

Nothing negative to say.

Submitted on July 7th, 2022 by Hasten Parker

The original web site has been removed due to fraud. Our entire team tried to make the software work. Nothing they had would integrate into Quickbooks, Posting Boards or RMIS. They said is was seamless. What a joke. We canceled after the 3rd month and they refused to reimburse our cost after they fraudelently charged our company credit card for an additional six months. There is currently a law suite pending. Stay away from this company and the software. We have been in the trucking business 21 years and the software and the support is a joke.

The Good…

That we canceled it!

The Bad…

No support, Nothing integrates and the software is nothing more than MapQuest with a coloring book.

Submitted on July 22nd, 2020 by Natalia S

We have enjoyed working with Tailwind over the past four months. Not only because the application fits our needs as a small, growing truck company but, beyond all that, their staff is genuinely interested in our success as a business. I know that if I have a question or a concern that I can count on the Tailwind team to help me. Sometimes they are truly amazing wind of comfort at my back. We operate in South America and we have appreciated how they have worked with us to apply the software to our particular situation. As a result we have been successful to date and are now growing quickly. Muchas Gracias!

Submitted on July 22nd, 2020 by Mitchie E

The software is good for tracking shipments and for the visibility it provides for all of our employees. Anyone in the office can pull up the orders and dispatches and know exactly what is happening. We phone in to the support department to ask for help with invoicing and generating reports. I appreciate that they get back to us promptly, within the same business day, and that they have a great way to connect with us on an interpersonal level. The software is easy to learn and we know who to call to get our questions answered. The support department is great at explaining the system to us in plain language that we can understand. As our business grows we continue to learn about how the system can help us further.

Submitted on July 22nd, 2020 by John T

Tailwind is very user friendly and has customizable features that can be done at the user level or through their support network. Run into an issue? Just call or email their support team, responses are always quick and solutions just as good.

Submitted on July 22nd, 2020 by Travis A

Tailwind is easy to use, and very compatible with our needs. The support staff is helpful. We have had great business success with Tailwind.

Submitted on July 22nd, 2020 by Danita M

We have been fortunate to be able to utilize the Enterprise version of Tailwind which has proven to be a very effective solution for TEAM. We offer a multitude of services and over 300 pieces of various equipment servicing the ports, containers, value added services including destuffing/stuffing, specialized equipment addressing heavy haul requirements and tanker units for bulk product. Tailwind can accommodate our diversity and effectively track our customized orders and equipment, adding seemless customer service and satisfaction. Order entry is simple and tracking is quick and easy. One of the features that has added to our customer satisfaction is the ability for our customers to track their own shipments. Our trucks are all required to have GPS/satellite tracking enabling our customers to monitor their live loads as well as their invoices and billing and effectively view their entire account. Orders have all pertinent information and related documents attached in the system and can be emailed directly to the customer’s designated representative allowing for quicker invoicing and turnaround for receivables. Another enjoyed feature is that everything is customizable and we are able to generate customer specific reports and invoices, in addition to a multitude of other internal forms which enable us to effectively monitor KPI’s.

From an accounting perspective it has also expedited our IFTA and driver pay. The wizards in the system make driver pay quick and easy to review outstanding payments to the driver. Automatic payables calculate driver pay for both company drivers and owner/operators, based on the criteria set at the initial setup of the software and credentials can easily be amended or necessary changes made.

The quoting module has reduced duplicate entries and historical data can be quickly accessed. Future follow-up and scheduling requirements can be logged and reminders set in the quoting module to ensure we don’t miss out on any opportunities or projects.

Tailwinds allows for smooth work processes and efficiency with minimal staffing requirements allowing for greater profitability and the system and execution are simple and very user-friendly.

Submitted on July 22nd, 2020 by Ron T

We have been using Tailwind since 2005 and could not be happier with the program. This program has increased our efficiency within our company. The over the phone training they offer was convenient and easy to comprehend. They are very friendly and always ready to answer any questions that we have. The system is very user friendly. It is so easy to enter new orders, make corrections, research and do invoicing. We also like how easy it is to look up the company financial sales, cost and receivables by using the report function that is available. We highly recommend this program; it has been a number one tool for us.

Submitted on July 22nd, 2020 by Handeep S

Tailwind has made our daily routine much easier and efficient. Tracking equipment, payables and receivables, as well as, sending orders and quotes is quite simple. Tailwind’s support department is good, anytime we have a problem we are able to get answers promptly. I did a little bit of training with Tailwind’s trainer, but I mostly learned how to use the system by navigating through it on my own. I found it easy to use, it made sense to me.

Submitted on July 22nd, 2020 by Pam L

What I really like about Tailwind is the customer support. The support team is responsive and appropriately reactive. The Tailwind software program is organized and user-friendly. We broker in our business, and had gone through the process of demoing several other transportation management systems. We learned that the other programs did not fit all of our business needs. Tailwind makes our work more efficient so that fewer mistakes are made. Once we enter in our information we can see the process from quotation right through to billing. Tailwind has helped our business to grow and become more profitable.

Submitted on July 22nd, 2020 by Tiffany M

Tailwind has been a wonderful company to work with! As a specialized transportation company, it was very difficult to find a software program on the market to fit our dispatch, accounting, and maintenance needs without breaking the bank. Tailwind has been able to meet all of our needs and is continuously adapting to make sure the software works for our business. The support team is very responsive and always finds an answer to our problem. We are still adjusting to a new software program, but we are thankful that we chose Tailwind!

Submitted on July 22nd, 2020 by Sarah R

Tailwind’s provides a clear board that uses a variety of colours and headings to make it easy to read and offers a great deal of information. The setup of the program is straightforward, allowing for smooth work processes. The error pop-ups provide a clear explanation of the problem so you know where and how to correct the error. They also have excellent customer support services with representatives who are able to explain things in a manner that is easy to understand. Overall, I would recommend this program to any dispatch in the industry. It is a very user friendly system that provides all the necessary information to complete the required daily processes.

Submitted on July 22nd, 2020 by Tarine M

I just want to thank you for everything you’ve done for us. I feel like sometimes I can really be a real pain in the butt but you always come through and help me in every way you can. I know it can be very frustrating at times. I know you are a very busy & dedicated individual and there aren’t enough people like yourself out there. You always make sure you return all my calls or at least e-mail me back, and to me, that goes beyond the call of duty. I just wanted to personally thank you for your excellent customer service. Thanks again

Submitted on July 22nd, 2020 by Lea B

Tailwind has given us greater visibility into our dispatch and invoicing, as well as our daily operational challenges. It is extremely rewarding to work with a company that has such exceptional customer service