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choose better software

What Is Tailwind TMS?

Web-based Trucking software - accessible from the office, home, or wherever you need to be. Start your FREE trial in seconds. Tailwind is built for trucking companies, freight brokerages, and those that do both. Our all-in-one TMS helps manage operations, customers, dispatch, admin, and includes a free POD capture app for all your drivers.

Who Uses Tailwind TMS?

Growing OTR trucking companies and freight brokerages looking for a TMS that is: web-based, versatile, scalable, intuitive, and affordable — with a support team there for you 24/7.

Tailwind TMS Software - See everything at a glance with list views and find any detail a click away
Tailwind TMS Software - Stay on top of every moving part with real-time data in every operations module
Tailwind TMS Software - In the customer portal, customers track shipments live, request quotes, and create new lanes in real time
Tailwind TMS Software - Text directly from Tailwind and receive instant updates and documents from drivers using the POD complete app
Tailwind TMS Software - Robust Accounts Payable and Accounts Receivable modules. Get paid faster with same-day invoicing, pay employees with ease in the personnel pay wizard.

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Reviews of Tailwind TMS

Average score

Overall
4.3
Ease of Use
4.3
Customer Service
4.6
Features
4.1
Value for Money
4.4

Reviews by company size (employees)

  • <50
  • 51-200
  • 201-1,000
  • >1,001
Audrey
Manager in Canada
Transportation/Trucking/Railroad, 501–1,000 Employees
Used the Software for: 2+ years
Reviewer Source

Worthy of managing your transportation needs

5.0 3 years ago

Comments: Automated BOLs - I have been working manually so long this is a small but necessary function.

Pros:

I like the ease of use. I have been able to train people remotely which is necessary at this time. Anyone I train seems to manage navigating it with ease.

Cons:

Nothing I can think of - it works fine for the functions I require of it.

Envase Response

2 years ago

Audrey, thank you for your detailed review of Tailwind! After more than two years with us, your high marks across the board carry a lot of significance. It is great to know that you have found the platform to be very intuitive, and are able to easily onboard new employees as you scale your company. We are so glad that Tailwind was the right fit for your business, and we look forward to growing with you every step of the way!

Michelle
Operations Manager in Canada
Transportation/Trucking/Railroad, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Operations Manager

4.0 3 years ago

Pros:

Fairly easy to use. Relatively straight forward.

Cons:

Poor transaction history and being able to see who did what in the system. Have to go to help desk for that. Not necessarily the right fit for a heavy haul operation, more suited towards brokering and more basic legal and OD loads. On that side it is fantastic. Cannot copy anything but orders - would be nice to copy quotes as well. Definite reporting limitations as well. Help lookup on specific topics is limited and not as detailed as it should be. Have to rely on helpdesk to answer some questions and it is frustrating to not be able to speak to a person and have to do it all through chat.

Tiffany
Operations Manager in US
Transportation/Trucking/Railroad, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Long Time Customer Disappointed in the New Platform

1.0 3 years ago

Comments: Was a great company when we signed in 2015, now we are just a number and there is no urgency to help us with needed things in the system.

Pros:

Multiple pieces of equipment dispatched with one order.

Cons:

Unable to copy quotes. Features from prior Tailwind software not available in the online platform. No more updates were provided in prior in version basically forcing us to go to the new platform.

Envase Response

3 years ago

Hi Tiffany, We're sorry to learn about your experience. Unfortunately we had to discontinue our legacy application and move to Cloud-based as the market (and staff to support) on-premise is shrinking. We know that changing systems is hard, which is why we continue to support customers on our legacy application even though we haven't sold it in over five years, and in your case, recently provided you with six services hours for specific customizations you required at no charge. I also know that you had recently submitted a feature. As development resources aren't unlimited, we try to implement requests that benefit the greatest number of customers first. Sometimes that means that very specific features for individual customers don't get done right away. Tiffany, as we do for all of our customers, we value your business. We are not saying that won't fulfill the feature request you have asked for - we just have to prioritize it along with requests from other customers.

Tyler
President in US
Logistics & Supply Chain, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Great for a new Broker

5.0 4 years ago

Comments: We are a 3rd party broker that needed a software to create load confirmations and Invoices. This software perfectly achieves that task and a good price.

Pros:

Over the last 3 years we have had no issues with the software breaking at any point. When I log in I am confident the software will work and allow me to complete the tasks at hand. This is big as down time due to software bugs isn't something that would be acceptable.

Cons:

Minor nuisance, when a repeat carriers liability insurance expires there is no way to make this change within the current dispatch you are working on you most exit and edit that specific vendor and then go back into the dispatch to create the required load confirmation.

Envase Response

4 years ago

Hi Tyler, we are glad to hear about your positive experience using the software. We look forward to helping you feel the wind at your back as your company continues to expand!

Caroline
Owner in US
Transportation/Trucking/Railroad, 2–10 Employees
Used the Software for: 1+ year
Reviewer Source

Daily Use System

4.0 3 years ago

Pros:

We love the ability to follow a load from it's creation, to dispatch, to invoice and remit of invoice. Allows for ease of driver, both o/o and company driver settlements ensuring accuracy. Customer service is great.

Cons:

Occasionally orders are too large to invoice and have to be done manually. Also occasionally invoices mysteriously don't post, however they have worked with us and tried to sort that out.

Patty
AccountingSpecialist in US
Transportation/Trucking/Railroad, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Bad

1.0 3 years ago

Pros:

There is nothing that I really like about this software.

Cons:

I have to size ALL my paperwork because of the transmissions fail on most every single one that has to be sent to customer. Also there is no way to see if the invoice sent. It states that it was sent but a lot of the times it does not make it to the customer.

Envase Response

3 years ago

Hi Patty, Thank you for your feedback. I'm not sure why your specific transmissions may be failing, but I have let our support and tech team know and they are investigating. If you can further elaborate using the in-app chat within the Tailwind TMS we may be able to get to the bottom of it faster!

Christie
Accountant in US
Transportation/Trucking/Railroad, 11–50 Employees
Used the Software for: 1+ year
Reviewer Source

It is a good start to perfect.

4.0 4 years ago

Comments: Tailwind TMS is better than the program we were previously using but it is not exactly how I would like it to be. I look forward to more development of features and programs.

Pros:

The software has made some aspects of the organization and implementation of information and data entry easier and more effective. The developers are always making updates to streamline everything but there is more work to be done.

Cons:

There are some features that don't make sense and others that need to be fixed to be more effective. I wish that we had more control of features and it was easier to get changes made.

Envase Response

4 years ago

Hi Christie, thanks for sharing your feedback, we appreciate it! We are always developing more features and updates to ensure our customers are getting the best experience. In fact, since the web-based version of the TMS was launched in November 2016, we've made over 300 updates and enhancements to it!

Jamil
President in US
Transportation/Trucking/Railroad, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Best TMS for the Money

5.0 3 years ago

Comments: Great support team, helped immidiatly

Pros:

Easy to use, does everything we need it to do

Cons:

ALl is well, nothing bad that I can think of

Envase Response

2 years ago

Thanks for your feedback, Jamil! We are very pleased to hear that Tailwind met all of your needs and helped your business grow. Our team works hard to provide the best support and guidance in each interaction, so we are glad you have enjoyed your experiences and that we provided the help you needed promptly.

Cole
Operations Manager in US
Logistics & Supply Chain, 2–10 Employees
Used the Software for: 1+ year
Reviewer Source

Great Product

5.0 4 years ago

Comments: Tailwind is an excellent product that has allowed me to expand in a capacity that would not be managable

Pros:

The product is very easy to use and is packed with many useful features. The ability to track all your orders, drivers, and carriers is very valuable and could not be replicated with just and excel spreadsheet.

Cons:

The ability to create and generate settlements for vendors could be a useful feature.

Envase Response

4 years ago

Hi Cole, Thanks for your Tailwind TMS review! To note - we do provide the ability to create payments and the remittance advice acts as a settlement statement for Vendors, showing what they are being paid for. And we also do settlement statements for Owner Ops (some companies consider them as vendors). If you need some assistance with this - you can reach out to our support team via email ([email protected]), phone (1-866-441-0441), or through the live chat in the application (where you'll get the fastest response)! Thanks again for your review! Brad from Tailwind

Genevieve
Safety Coordinator in Canada
Transportation/Trucking/Railroad, 11–50 Employees
Used the Software for: 1+ year
Reviewer Source

Could be better

4.0 4 years ago

Pros:

Being able to look back at any information, finding everything a particular truck/driver/trailer did for a certain time period. It has a lot of reports. All these were not available with the last program we used but we did not have a dispatch program prior to Tailwind. Tailwind is user friendly once you get to know your way around.

Cons:

Support could be better, we have requested some add ons a few months ago and we've had no word on when this would take place. Some of the changes made by Tailwind seemed unnecessary and caused more issues for us.

Envase Response

4 years ago

Hi Genevieve, thanks for the feedback! We will take a look into your suggestions to see what changes need to be made in order to provide an optimal experience. Our support team is usually very responsive especially in the in-app chat, so we will review what happened there.

Sheri
Dispatch in Canada
Transportation/Trucking/Railroad, 11–50 Employees
Used the Software for: 1-5 months
Reviewer Source

Keeps our boys moving

3.0 4 years ago

Comments: Overall my experience has been alright

Pros:

ease of use for everyday to use in my dispatching.

Cons:

Down time due to online use instead of Software use.

Francois
President in Canada
Logistics & Supply Chain, 2–10 Employees
Used the Software for: 6-12 months
Reviewer Source

Tailwind is very user friendly

5.0 3 years ago

Comments: Loving it

Pros:

Very easy to use and to train new staff to use.

Cons:

When working of the order list or dispatch list, when you get out of the order or dispatch, you lose all the filters applied.

Jeff
Operations in Canada
Transportation/Trucking/Railroad, 2–10 Employees
Used the Software for: 1+ year
Reviewer Source

Tailwind Review

4.0 4 years ago

Comments: It gets the job done. Learning has been through application and no real upgraded training takes place.

Pros:

Fairly intuitive to use. Once the basics are learned, it is straight forward.

Cons:

There is no flexibility. For example, there is information I want every day that needs to be put into Excel and then pared down to what I require. Report ideas were submitted but nothing ever happened.

Envase Response

4 years ago

Hi Jeff, we appreciate your feedback! As our software continues to evolve, we are looking to implement more customer suggestions, thanks for the review!

Sheila
Office Manager in US
Transportation/Trucking/Railroad, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Tailwind TMS

5.0 4 years ago

Comments: It is easy to use.

Pros:

I love that it integrates with QuickBooks Online. This makes it easy for our accounting side of operations.

Cons:

Occasionally the drivers have problems seeing their load confirmation information. This mostly has to do with our owner/operators.

Envase Response

4 years ago

Hi Sheila, thank you for the review!

Erin
Owner in US
Logistics & Supply Chain, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Great support, agile platform.

5.0 4 years ago

Pros:

We love tailwind and have used it for several years. We would recommend this service to anyone looking for an affordable, highly functional TMS.

Cons:

None! Tailwind is easy to use and fulfills all of our needs.

Envase Response

4 years ago

Hi Erin, Thanks for the great review, we appreciate it!

kevin
Vice-President in US
Transportation/Trucking/Railroad, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Tailwind review

5.0 4 years ago

Comments: Very positive!

Pros:

Helped us expand our business and provide customer data quickly. Easy to use and learn!

Cons:

Didn't integrate with our accounting software. Sage.

Envase Response

4 years ago

Hi Kevin, we're happy to help you as your business grows!

Ricky
Operations in Canada
Transportation/Trucking/Railroad, 11–50 Employees
Used the Software for: 1+ year
Reviewer Source

Review

4.0 4 years ago

Comments: This helps us in our day-day operations and provides a one-stop solution for operations and invoicing.

Pros:

Ease of use, practical and intuitive interface.

Cons:

Reporting features are inaccurate are do not seem to be getting fixed.

Envase Response

4 years ago

Hi Ricky, we appreciate your review and the feedback as we continuously look to make improvements to the software!

GURPREET
DIRECTOR in Canada
Transportation/Trucking/Railroad, 2–10 Employees
Used the Software for: 1+ year
Reviewer Source

Best software

4.0 4 years ago

Pros:

The best about Tailwind is about making Invoices

Cons:

Nothing Such is have about the software but just want to learn more about making owner operator invoices as that's bit complicated

Envase Response

4 years ago

Hi Gurpreet, thanks for taking the time to leave us a review!

David
Owner in US
Translation & Localisation, 2–10 Employees
Used the Software for: 6-12 months
Reviewer Source

Review

2.0 4 years ago

Comments: This program solves the base problem of needing to send rate confirmations and build shipments but I have yet to think about switching over my quick books due to the incredibly slow speed of the site and multiple crashes per week.

Pros:

Easy to build shipments and understand how to affect the format.

Cons:

The speed of the platform is incredible slow and at least every other day my colleague or myself have the website crash.

Bob
President in US
Transportation/Trucking/Railroad, 2–10 Employees
Used the Software for: 1-5 months
Reviewer Source

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

5.0 8 years ago

Comments: 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.

Ashley
Digital Marketing Manager in US
Hospitality, 11–50 Employees
Used the Software for: 1+ year
Reviewer Source

Helpful Pinterest Support

4.0 6 years ago

Comments: We use Tailwind to populate Pinterest pins from website, blog, and social media content. It has been super helpful in tracking pins performance.

Pros:

I love how easy it is to use- simple and worth the time put in for the results.

Cons:

Having multiple team members operate our one account has ha some snags.

JAy
Lead dispatcher in Canada
Transportation/Trucking/Railroad, 2–10 Employees
Used the Software for: Not provided
Reviewer Source

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

5.0 8 years ago

Comments: 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

Jim
Operations Manager in US
Used the Software for: Not provided
Reviewer Source

This software IS awesome!!

5.0 9 years ago

Comments: 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

Dean
Principal
Used the Software for: Not provided
Reviewer Source

I would recomend this program to anyone who is interested in have a user freindly program.

5.0 16 years ago

Comments: I would recomend this program to anyone who is interested in have a user freindly 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.

Pros:

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

Cons:

There are no cons to report.

Kourtney
US
Used the Software for: Not provided
Reviewer Source

Excellent

5.0 9 years ago

Comments: 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