What Companies Say About Tailwind Transportation Management Software (TMS)

Tailwind provides industry leading software for companies who both operate trucks and broker loads. Take a look at what they have to say.


“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!”

– Natalia S., AT Cargo

“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.”

– Mitchie E., Keene Freight Logistics

“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.

– John T., ATS Logistics

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

– Travis A., Operations Manager, Western Heavy Haul

“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.”

– Danita M., Logistics Manager,  Team Transport Group

“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.”

– Ron T., Delaware Dist

“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.”

– Handeep S., Trans-Logic Truck Lines

“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.”

– Pam L., General Manager, Universal Freight & Transportation Inc.

“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!”

– Tiffany M., Operations Manager, Precision Heavy Haul, Inc.

“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.”

– Sarah R., Campbell Freight Inc

“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”

– Tarine M., Ten Berge Transportation

“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”

– Lea B., Dispatch Manager, Moonlight Freight, LLC

What Freight Brokers Say About Tailwind

We can talk about Tailwind freight broker software all day – but it’s what our customers say that really matters. 

“As a startup business I easily completed integration and worked efficiently from day one. The invoicing is very detailed collecting information from the normal workflow of dispatch to billing. Tailwind has developed a very powerful platform with customizable features for any size business. During integration their customer support via live chat that stays with you on each screen is amazing. It’s as good as having an in house IT department in your office working on your system all day. Truly amazing customer support. The training videos allows you to continually go back and learn the basics. The way the system operates and the access to training videos, makes on boarding new employees a snap. They basically do it for you with all of the videos. Lynda is the dedicated trainer and she rocks!!!!”

– Bob K., XLENT Industries

“I have had a great experience with the software. The staff is very responsive and would gladly be able to train me on anything I need to know.”

– Ryan V., Available Trade International

“The software is easy to understand and provides all TMS functions from dispatch, AP, AR, to account management reporting. It has some nice features due to its integration with mileage programs, posting sites, and reporting. Tailwind supports multiple users and most importantly works using multiple currencies for CDN and USD.

Greg D.,VP Sales and Operations, SPI International Transportation

“We began searching for an operations software package in early 2007. After investigating a number of systems, we found Tailwind. The Tailwind staff made the transition from manual to automated very easy. They were all very professional and maintained timelines that were very tight.

Tailwind helped us to adapt forms (quote, Load Contract, etc) to look and feel like the manual systems so that it was a seamless change for our customers and vendors. And they didn’t nickel and dime us every time we needed something changed. They provided excellent on site and after regular business hours training as well as distance service.

At the same time, we needed to change accounting systems to fully utilize Tailwind and their staff made the transition as painless as possible with real help for our accounting personnel.

We’ve been operating with the system in place for about 16 months and every issue that we have had, and there have not been many, have been addressed quickly and professionally by the Tailwind staff.

My background is the courier industry and I have been involved in purchasing, installing and training three different operations systems like this and the problems were horrendous; timelines were constantly missed, we were left on our own to solve issues and each offered their own different problems. Those problems affected our operational abilities and our bottom line. I highly recommend the Tailwind operations system to anyone who is interested.”

– Rod W., Lantrax Logistics

“We have been very pleased with our decision to implement TAILWIND as our primary operations and tracking software. As a distribution/warehousing business with three locations stretching from coast to coast, our information has to be available to all locations. TAILWIND’s software has allowed us to centralize all of our information into one database, with up-to-date tracking information available at all times. Our customers are able to access the tracking system and feel confident about the information in front of them. We would proudly recommend TAILWIND software without hesitation!”

– Chris W., Gateway Distribution Inc.

“There is no other way to go than being on a maintenance and support plan with Tailwind. I have noticed a huge improvement with the new Customer Success Platform that is being offered. Previously, we were not using the system to its full potential. Angelena reached out to us this year and ensured that we are receiving the attention we require. Specifically, as a Platinum customer I will receive a one on one session with the “awesome” Lynda Clare. I am confident that as a result of this intervention we will receive all the help we need to learn how to use the system comprehensively and to run reports that will further align my business needs with the Tailwind Software. If we have a technical problem your support team helps us immediately and our issues are resolved. I have enjoyed the stability of your support team; Mark, Sandy, Egi and Richard are all great at their jobs and walk us through to the answers we require. Working with Tailwind in 2016 will enable me to get my Trucking business to the next level of success.”

Kevin A., Vice President, Target Transportation

“Lynda is our trainer from Tailwind. All of us here at RPM Expedite Inc. were trained by her on how to use Tailwind. Lynda is extremely knowledgeable and every time if we needed something quick, she always try to resolve our problems right away. We could not ask for any better trainer than her, she explained and showed how to use the software extensively. We really appreciate her efforts and look forward to have our new employees trained by her in the near future.”

Betty Y., Controller, RPM Expedite

“Tailwind is awesome from top to bottom. It has been a pleasure to work with all the support and sales staff at Tailwind. The software saves us an incredible amount of time, our dispatch process has become streamlined thanks to Tailwind. We were an old company that was resistant to change and are extremely grateful to have found Tailwind. The training and support has exceeded our expectations. We flew out your Trainer to teach us how to implement the software and the investment was worth every penny. The training was the key to being able to use this system. I would recommend Tailwind over the alternatives, no hesitations.”

Mark A., President, MAC Freight Services

“All of our information is easily and readily available to us with pinpoint accuracy. Our customers are happier, more informed and better taken care of since we installed the software. We can quickly and accurately track our customers’ loads and update them at a moment’s notice on their shipment status. We do not misplace or lose orders anymore and that has saved us time and money. If an order is not delivered it cannot be billed. Even if the paperwork is misplaced and the order delivered, we will still have the order in the system to bill. The ability to sync to our accounting makes our accountants job easier.”

Jamie P., Polar Express

“Very user friendly, very simple and easy to find information. I can get information from 3-4 years from using the system about driver, power units, trailers, customers, vendors etc…”

Balihar M., Sam-X Logistics

What Trucking Companies Say About Tailwind

It’s easy for us to talk about Tailwind trucking software, but don’t take our word for it. See what trucking companies have to say about Tailwind.

“We needed a system to make confirmation sheets and were using pen and paper to run our business. I contacted Tailwind and had a demo with Lynda. We got our logins and watched two training videos on our own time. The program was super easy to learn on our own. It was extremely self-explanatory. It took me one month to learn how to use the system. I could have learned it in one week, but I was really busy at work. If I had a question, I got an answer from your support department and your trainer within 1-2 hours. Tailwind stayed in touch with me regularly. I never felt alone in learning how to use the system. Now our business is more organized and I can work from home when I need to.”

– Kourtney H., Seven Oaks Dairy LLC

“ Tailwind has grown and it shows.  Your customer service is incredible. I love learning and your support team can teach me how to tackle my software issues.  When our companies work together to build a relationship we both can achieve success.  Our old system was DOS based and when we upgraded our computers we needed to get a new Transportation Management System.  After a year of using Tailwind, I feel like I understand how to use the system, I can get help when I have a problem and I have the ability to cross-train with my staff so the system is continually adapting to our evolving business needs.”

– Roxanne L., HR & Accounts Payable, Specialized Equipment Systems

“Before Tailwind, we weren’t using any software to manage our operation and everything was handled by pen and paper. That did the trick while we were small and only had a few trucks, but once we started to focus on growing the company, we knew we needed a good system to help us grow. 

Tailwind has been really great and is a crucial part of our business. It helped us grow. Paying owner operators and keeping track of everything would be impossible without Tailwind.

The software itself is great, but more importantly, the training and support is superb. Tailwind’s staff has always been there to help us from the beginning, and I would recommend it to every trucking business out there.”

– Pardeep A., CEO, Triple Eight Transport Ltd.

“The technical support is thorough, responsive and helpful at Tailwind.”

– Tom O., EMH Transportation LLC

“Tailwind dealt directly with my interest and provided patience along with understanding and an open mind for the specific requests. Tailwind’s employees have carried these same customer service elements in our day-to-day communications over the past few years and continue to value me as if I was their only customer. Your team’s ability to reconfigure your programs functionality at any given notice has separated you from your competition by a country mile.”

– Justin D., Cassidy’s Transfer & Storage Ltd.

“We were able to adapt the Tailwind platform with ease and the learning curve was short. System has a lot of functionality and the support by their staff is excellent! Greatly enhanced our capability to manage our transportation services.I would definitely recommend Tailwind!”

– Kevin J., RLS Global, Inc.

“We are a small company, it’s just me, my employer and 5 drivers. We just received our authority two years ago. The old software we were using was very tedious and I never heard back from their support department when I needed help. With Tailwind I can punch in 5 dispatches in less than 15 minutes, it used to take me about an hour. I save a significant amount of time using Tailwind. The training is wonderful, I appreciate the Q&A classes and the structure that is available to learn how to use the system. Your trainer is quick to accommodate and can answer all of my questions. Tailwind’s support department is incredible, I have a solution to a technical problem within 20 minutes they have called me directly instead of sending me emails, making it easier for this old dog to learn new tricks.”

– Jim L., Woody’s Trucking

“I could not be happier with the service I’ve received.  You supplied me with a great product years ago and it just keeps getting better. I regularly recommend Tailwind to others.” 

– Mike K., Owner, MSK Transport

“This is a very user friendly program. All features are great and can be user altered for their own preferences. Tailwind provides excellent support and is willing to work to meet your needs.

I would recommend this program to anyone who is interested in have a user friendly program and a support staff second to none. The cream of the crop as far as support goes. I have never experienced anything as good.”

– Dean V., Sunfire Transport

“Order entry and dispatching are easily handled with Tailwind. It’s good value for the money spent and I would recommend it to others.”

– Yvonne H., Motrux

“This system is great for trucking businesses. It is fairly easy to learn and has lots to offer. I have yet to stop learning new things from this system. The Driver Pay Wizard is very handy for my department. I am able to immediately determine if PRO#s have or have not been paid to a driver. My old method was to look through every check they have received from us! Customer support is always there to help! Thank you Kenny and Kyle.”

– Dana N., A&J Transportation