Tailwind Transportation Software offers a cloud-based transportation management solution built for small to mid­size trucking companies and freight brokerages. Tailwind features a customer and vendor database, quoting and order modules, a dispatch system and more.

Tailwind’s customer and vendor database allows users to track and maintain contact information. Users can manage quotes, work orders and accounts receivable, view customer rate histories and track equipment maintenance, claims, incidents and accidents. Tailwind also features a dispatch and shipment tracking system, route management and user alerts.

Tailwind features a sales commission system, preconfigured admin, accounting and operations reports and a data import tool, as well as QuickBooks sync. The system also offers IFTA mileage tracking, load board integrations and a dedicated mobile app. Driver and carrier settlements, GPS integration and a customer portal are also available.

Phone, email and in-app chat support are available. Pricing is per user per month with no contracts necessary.



43 Reviews of Tailwind Transportation

Overall rating

4.51 / 5 stars

Filters:

Showing 1 - 20 of 43 reviews

January 2019

Scott from O'Brien Logistics

Company Size: 2-10 employees

Review Source: Capterra


Ease-of-use

2 of 5

Value for money

2 of 5

Customer support

2 of 5

Functionality

5 of 5

January 2019

Powerful Tool - And Slow

Lehmans terms could assist with training new people on the software.

Pros

It has a lot of bells and whistles which we find are useful, from payroll to Quickbooks integration. Support is responsive Monday - Friday.

Cons

Very slow, we used multiple browsers, Mac and Windows, in addition we have used several wifi points to ensure it was not our internet. We compared this TMS to some other online trials and these systems responded much better.

Concern Tailwinds may be a thing of the past for us, we are a fast moving business and the product is becoming a thorn in our side.

Response from Tailwind Transportation Software of Tailwind Management Systems

Replied January 2019

Hi Scott. We are sorry to hear you are experiencing slowness with your application. I see that some adjustments were made to your system a few days ago which hopefully should have helped. Regardless, we will be in touch to help rectify the problem.

December 2018

Larry from LF Logistics Company

Company Size: 2-10 employees

Review Source: Capterra


Ease-of-use

5 of 5

Value for money

5 of 5

Customer support

5 of 5

Functionality

4 of 5

December 2018

Tailwinds is my office support staff

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

Pros

There are many features that make it the ease of taking little time for paperwork when doing dispatch and keeping track of loads. You will have information on Loads, Customers, Vendors at your fingertips There is a superb support staff that is there to help.

Cons

I have a hard time finding something i don't like Are there some that could improve? Yes and they have worked on them and made them 100%

December 2018

Simon from Ready Freight Ltd

Company Size: 2-10 employees

Review Source: Capterra


Ease-of-use

5 of 5

Value for money

4 of 5

Customer support

5 of 5

Functionality

4 of 5

December 2018

User friendly and highly functional hosted TMS

I was up and poking around the system within a day. Tailwinds set me up with live training webinars which gave me a good tour of the system functionality. There are more (free) in-depth webinars available which I haven’t taken yet, but the system is so intuitive and easy to use that I haven't felt the need to. Data is easy to export to work in spreadsheets. Forms are all there like invoices, bol, etc... Tech support is very responsive and easy with the the online chat and phone.

Pros

I was able to setup my new Freight brokerage business and be up and running with my first loads within a week of getting setup on Tailwinds.

Cons

I wish is was more customizable. Specifically the email forms from the system. Being able to customize email subject lines with data variables, etc..

April 2018

Daniel from Naked Lady Trucking LLC

Company Size: 2-10 employees

Review Source: Capterra


Ease-of-use

4 of 5

Value for money

4 of 5

Customer support

5 of 5

Functionality

5 of 5

April 2018

Robust trucking software that is pleasant to look at with great customer support

Aesthetics was a huge consideration, and who ever designed this software had feng shui in mind, great to look at!

Pros

You will appreciate the customer support you receive with this software. Tailwind is easy enough to use and very pleasant to look at (which is important if you have to stare at this software for several hours a day). However, the true strength of this offering comes from the company's dedication to making sure that you understand how to use the software and get the most out of it. They have great training videos, and you can set up a personal training session. Everyone I have talked to there is super pleasant and eager to help. Other software companies just hand it to you and say, figure it out and let us know if you need anything. Not Tailwind. They generally want to make sure that the software is a good fit for you and will do back flips to make sure you get what you need. The tip about using multiple browser tabs with different pages of the software open to quickly move between sections, while obvious once you use it, was a great idea I didn't initially think of.

Cons

It's a bit expensive for a smaller company, but as you grow, they can be flexible with adding features/users for a discount.

March 2018

Jason from Orangedale Transportation

Review Source: Capterra


Ease-of-use

5 of 5

Value for money

5 of 5

Customer support

5 of 5

Functionality

5 of 5

March 2018

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

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.

Pros

I went through an extensive TMS review when starting my own freight brokerage. Having used several of the biggest names in TMS in the past, I was expecting them to lead the pack. After my evaluations were complete, I found that Tailwind had an extremely robust set of features that were all web-based at an affordable price. Being able to sign into the TMS system on any device with an internet connection has been a life saver while traveling.

They have a great customer portal that allows customers to log in and see the status of their shipments live as they are updated, which saves a ton of time and makes communication easier. Customers have told me that our TMS is better than companies 100 times our size. In the rare event that the software is missing a feature that would be helpful, they listen and bring suggestions to their development team. Several of my suggestions have been rolled out as updates.

Their customer service is top notch. They have an extensive knowledge database with articles and videos for almost every topic and a responsive customer service team that always answers questions quickly through their online chat or on the phone. Tailwind also offers weekly live training sessions that got us up and running in just a few days.

In starting a new business, choosing Tailwind TMS was one of the best decisions I have made. I would recommend this software to anyone looking for a great TMS solution.

Cons

The only cons I can think of is that they don't have an iPhone app (but I am able to log in through the browser) and their sorting options for shipments in the system could be a little more robust. You can save what items are shown on different screens, but are unable to save a sorted view (i.e. always show the list in order of pick date).

August 2017

Natalia from At Cargo

Company Size: 2-10 employees

Review Source: Capterra


Ease-of-use

5 of 5

Value for money

5 of 5

Customer support

5 of 5

Functionality

5 of 5

August 2017

The culture of Tailwind is quality and everyone is very knowledgeable, helpful and kind.

All I need to make our business going : Database, Accounting & Administration, Equipment and Driver Management, Quotes and Orders, Alerts and Load Tracking & Reporting. Among many other operations. Thank you, Tailwind!

Pros

The fact that Tailwind is an "all in one application" helps us run the business more effectively and we have access to it from any device. The features are unique and the platform is constantly improving to fulfill every need.

Cons

I have a hard time coming up with something because if I do have an issue that needs to be resolved right away, I immediately have a solution from Tailwind's support system.

June 2017

Bob from XLENT Industries

Company Size: 2-10 employees

Review Source: Capterra


Ease-of-use

5 of 5

Value for money

5 of 5

Customer support

5 of 5

Functionality

5 of 5

June 2017

Customer Support is superb! They develop software targeting user feedback. Best service in my book!

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!!!!

Pros

Dispatch and operation work flow. New order screen has all features on one page. This was created after listening to customer feedback. Their updates happen so fast following feedback, big thumbs up to the development team.

April 2017

JAy from NovaTrans Logistics

Company Size: 2-10 employees

Review Source: Capterra


Ease-of-use

5 of 5

Value for money

5 of 5

Customer support

5 of 5

Functionality

5 of 5

April 2017

Easy to use with excellence!! Sophisticated and very well designed!

IN the past, I worked on different dispatch software, however, when I was introduced to TAILWIND, I fell in love with it. It is very user friendly, outstanding technical support, very well organized training with super friendly TAILWIND team, who are always there for you, whenever you need them...........TAILWIND rocks my transport dispatching world!

Pros

User friendly, excellent technical support, friendly team

Cons

Nothing I can think of right now

January 2017

steve from XLG Transportation Inc

Company Size: 11-50 employees

Review Source: Capterra


Ease-of-use

5 of 5

Value for money

5 of 5

Customer support

5 of 5

Functionality

5 of 5

January 2017

Great Software Very User Friendly

Just got off the phone with rep and I wanted let everyone at Tailwind know how impressed we are with your system. This is the most user friendly and customizable software we have looked at. You are headed in the right direction because not everyone does it the same and you have created your software with that understanding in mind. Thanks for all the hard work and listening to our ideas and being able to make those ideas work.

Pros

They have simplified the settings to the point you can customize it to fit your business whether its asset based or brokerage or owner operators

Cons

I have not found anything i dont like they have addressed all our concerns and adjusted their software to fit us

June 2016

JOHN from ATS Canada

Company Size: 11-50 employees

Review Source: Capterra


Ease-of-use

5 of 5

Value for money

5 of 5

Customer support

5 of 5

Functionality

5 of 5

June 2016

Excellent TMS

Tailwinds 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.

Pros

We are continuously utilizing more and more of the components of the software every day. TW can be as small or as large a part of your TMS system as you want it to be.

June 2016

Pamela from Universal Freight & Transportation Inc

Company Size: 11-50 employees

Review Source: Capterra


Ease-of-use

4 of 5

Value for money

4 of 5

Customer support

4 of 5

Functionality

4 of 5

June 2016

Tailwind is great!

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.

Pros

Data only needs to be entered once
Fewer errors
Allows tracking of previous loads so you can look at history to help with the future loads

Cons

There are a few bugs we are ironing out.

June 2016

John from Universal Freight and Transportation Inc.

Company Size: 11-50 employees

Review Source: Capterra


Ease-of-use

4 of 5

Value for money

5 of 5

Customer support

4 of 5

Functionality

4 of 5

June 2016

Tailwinds rating review

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.

Pros

It efficiency handles booking and costing of loads, has good credit capabilities built in for reference of potential credit issues, reporting is good with most being able for export to Excel if further analysis is needed, and the cost is reasonable for well working software.

Cons

Sorting capabilities should be based on more than one criteria. This would probably be an easy fix with TW software people.
Clients should get a workshop how to build report generators tailored to their business needs rather than requesting TW software team to built it.

June 2016

Gretchen from Reliable Source Logistics

Review Source: Capterra


Ease-of-use

5 of 5

Customer support

5 of 5

June 2016

Very pleases with the classes and satified with Tailwind

The training classes were informative and Lynda thoroughly answered all of my questions. I am very new to the transportation industry - Lynda took the time to explain the terminology to me so I have a better understanding of the industry in general and my business specifically. The program is fairly easy to understand once you go to training and if you access Lynda to have a private session. The program absolutely saves me time by helping me to get organized with my tasks. I deal with the accounting side of the business and because Tailwind has a colour coding system in place, I am able to see what invoices are due ahead of time. I will be able to get my invoices in and out ON TIME. My staff in the Dispatch side of the business tell me that Tailwind has really helped them to do their jobs well. Lynda, has a very nice demeanour and voice so she is not only knowledgeable but also very easy to listen to. Gretchen Hayes, Reliable Source Logistics Account Manager

June 2016

kevin from RLS Global, Inc.

Review Source: Capterra


Ease-of-use

5 of 5

Customer support

5 of 5

June 2016

Great Tool & People

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!

May 2016

Greg from SPI International Transportation

Review Source: Capterra


Ease-of-use

4 of 5

Customer support

3 of 5

May 2016

I have used the software since its inception and experience all the updates

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. CMS supports multiple users and most importantly works using multiple currencies for CDN and USD. Some sections need improvement because of extra page clicks, but I am told this will be addressed soon.

May 2016

Mitchie from Keene Freight Logistics

Review Source: Capterra


Ease-of-use

4 of 5

Customer support

5 of 5

May 2016

Useful, easy-to-use software and excellent customer support

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.

May 2016

Travis from Redmond Heavy Hauling

Review Source: Capterra


Ease-of-use

5 of 5

Customer support

5 of 5

May 2016

Great Product, easy to learn

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

May 2016

Kourtney from Seven Oaks Dairy LLC

Review Source: Capterra


Ease-of-use

5 of 5

Customer support

5 of 5

May 2016

Excellent

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 Haese Seven Oaks Dairy

May 2016

Ryan from ATI

Review Source: Capterra


Ease-of-use

5 of 5

Customer support

5 of 5

May 2016

Great!

I have had a great experience with the software there are a lot of functions included that I do not utilize however should I choose to the staff is very responsive and would gladly be able to train me on anything I needed to know.

May 2016

Handeep from Trans-Logic Truck Lines

Review Source: Capterra


Ease-of-use

5 of 5

Customer support

5 of 5

May 2016

Easy and efficient

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.