Tailwind Transportation Software

4.53 / 5 (45)

About Tailwind Transportation


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.



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Supported Operating System(s):

Mac OS, Web browser (OS agnostic), Windows 8

45 Reviews of Tailwind Transportation

Average User Ratings

Overall

4.53 / 5 stars

Ease-of-use

4.5

Value for money

4.5

Customer support

4.5

Functionality

4.5

Ratings Snapshot

5 stars

(29)

4 stars

(12)

3 stars

(3)

2 stars

(1)

1 stars

(0)

Likelihood to Recommend

Not likely

Very likely

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Showing 1-20 of 45 reviews

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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).

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.

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%

January 2019

Daniel from Super Shippers

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 2019

Tailwind Review

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

Pros

Is very flexible and you are able to creat the orders as you want

Cons

Traying to get automatic commsion payments for your personel can be tricky but once you get it done works great

Response from Tailwind Transportation Software of Tailwind Management Systems

Replied January 2019

Thanks Daniel - we appreciate the feedback!

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.

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.

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.

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 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

March 2016

Kevin from Target Transportation Ltd

Review Source: Capterra


Ease-of-use

5 of 5

Customer support

5 of 5

March 2016

Tailwind

"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, Eg 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 business to the next level of success."

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

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.

May 2009

Sarah from Campbell Freight Inc.

Review Source: Capterra


Ease-of-use

4 of 5

Customer support

5 of 5

May 2009

Overall, I would recommend this program to any dispatch in the industry.

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.

Pros

Tailwinds 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 popups 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, it is very user friendly.

Cons

The warnings can cause an inconvienence when they continuously popup everytime something is resaved. In addition, refreshing the screen can take a great deal of time in the receivables section.

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.

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

February 2016

Roxanne from California Specialized Equipment Systems, Inc

Review Source: Capterra


Ease-of-use

5 of 5

Customer support

5 of 5

February 2016

We made the transition from a custom DOS program to Tailwind last year 2015

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. In just 1 year Tailwind Support has grown and it shows. As a Platinum customer, when I call in with a technical issue, your support team answers the phone promptly and logs into my system to help me. They can see my screen, I love learning and your support team helps teach me how to tackle my software issues. Customer service is better than ever. I would recommend to all of your customers to choose a Platinum level Maintenance and Support Plan.

May 2016

Jim from Woody's Trucking LLC

Review Source: Capterra


Ease-of-use

5 of 5

Customer support

5 of 5

May 2016

This software IS awesome!!

We are a small company, it's just me, my emlpoyer 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 20minutes they have called me directly instead of sending me emails, making it easier for this old dog to learn new tricks

January 2019

Gilberto from Silveroute

Company Size: 2-10 employees

Review Source: Capterra


Ease-of-use

1 of 5

Value for money

3 of 5

Customer support

5 of 5

Functionality

4 of 5

January 2019

A little complex to learn

It is a good software to coordinate the freights once you learn how to use it.

Pros

That you can link it with your QuickBooks account.

Cons

It is very difficult to learn. It took me over a month to have a full understanding of it.

Response from Tailwind Transportation Software of Tailwind Management Systems

Replied January 2019

Thanks Gilberto, Regarding your comments on software complexity - please don't hesitate to reach out to us using the in-app chat with support for help as you need it. You can also attend our free LIVE training sessions that happen twice a week!

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