User Reviews Overview

Feature Ratings

Ease-of-use

4.5 / 5

Value for Money

4.5 / 5

Customer Support

4.5 / 5

Functionality

4.0 / 5

Ratings Breakdown

5 stars

(47)

47

4 stars

(24)

24

3 stars

(9)

9

2 stars

(2)

2

1 stars

(0)

0

  • Pros

  • "Easy to install, easy to use, great customer service. "

  • "User friendly. It is very easy to use. And when I can't figure something out, support is right there to help me! It is also affordable!"

  • "I like how easy it is to use the software, easy to navigate."

  • 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."

  • "Some integrations with QuickBooks can be confusing. But once you get a feel for how the two programs work together it becomes easier "

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

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December 2018

User Profile Picture

Larry from LF Logistics Company

Verified Reviewer

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

4.0

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 2020

Frank from NU Central Mass Auto Auction

Company Size: 51-200 employees

Industry: Automotive

Time Used: Less than 12 months

Review Source: Capterra


Ease-of-use

4.0

Value for money

4.0

Customer support

5.0

Functionality

3.0

December 2020

Transportation Software for an Auto Auction

Overall, I researched numerous Transportation Apps and this one had the best features for our industry. It seems more suited to brokers than an auto auction but it works well. The customer service has been exceptional. The price point is a little high considering the lack of GPS and driver's app functionality.

Pros

What I liked most about the software is that it is very versatile. It tracks everything for us from pickups and deliveries. For the first time, we are able to quantify the value of transportation in a market of ever-changing agreements and pricing.

Cons

What I like the least from the software is that the drivers App doesn't show enough information for the pickups and deliveries. Also, there is no GPS integration for the drivers. With other Apps, drivers can just press the address and it automatically sends them to Google maps or Waze. Additionally, there should be an integrated GPS for truck routes to avoid non-commercial routes, low bridges, and tight intersections.

Reasons for Choosing Tailwind TMS

Tailwind was the most comprehensive App on the market that I researched. I did over a dozen webinars with different companies and I finally settled on Tailwind. It's not perfect, but it has a lot of advantages for our company and industry.

Reasons for Switching to Tailwind TMS

The towbook app was great except that we couldn't clearly distinguish from pickups and deliveries. It was only $200 a month. Sometimes the App would crash holding our work hostage for an entire day.

Response from Tailwind Transportation Software

Replied December 2020

Hi Frank, Thanks for your review and the feedback! We will update our development team with your suggestions to see what changes may need to be made. Our integration with EZ-Track also provides you with free load tracking--25-loads tracked in our Pro tier, 50 in Enterprise, and unlimited tracking in our Unlimited tier!

December 2020

Richard from STS

Company Size: 51-200 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

3.0

Value for money

5.0

Customer support

3.0

Functionality

3.0

December 2020

Product quality

For our current size, it has checked the most important boxes. Critical Dispatch, billing, AR mgmt functions are covered for the most part. If we continue our growth we will have to migrate to a different platform without some developments on Tailwinds side. For reference, our we are a 45 truck fleet.

Pros

Easy to navigate. Web based platform. Reasonably committed to product improvement and feedback from end users.

Cons

Lacking integrations with outside vendors (specifically ELD platforms, EDI platforms, Load boards and tracking softwares). POD complete app is functional, but has issues with format and size of file when transferring to customers for invoicing. Seems like they could partner with a transflo or some other software that already has the software built to strengthen their offering. No admin app for viewing platform on tablet/phones. Reporting could use some adhoc capabilities.

Reasons for Choosing Tailwind TMS

Price, ease of use, ease of transition.

Reasons for Switching to Tailwind TMS

Previous platform was outdated, did not offer sufficient AR tracking capabilities, no ability to capture and transmit BOLs/PODs.

Response from Tailwind Transportation Software

Replied December 2020

Hi Richard, Thanks for your review and the feedback! Our recent partnerships with Kleinschmidt (EDI), EZ-Track and Trucker Tools (tracking) should help address some of your integration needs, and there's also an upcoming integration with Samsara (ELD) that will be announced officially soon! And there are more integrations slated for 2021 :-)

January 2021

Djuro from Cargox Inc

Verified Reviewer

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

January 2021

Tailwind TMS is the best you will find and love !!!!

Great software, but just that driver app needs work.

Pros

There is lots of pros here, its online based, and you should be looking at online based, no server or up front cost, and you can use it from anywhere. Software has all the things you can think of. Great reports, and you can store files on trucks, drivers, and all your exp data. You can dispach the load, customize the payables the way you want, There is ways to add deductions and fuel can be imported, for owner operstor deductions, and software will pay the truck not the driver as this is important for owner operators, and if they have there own drivers this ia probably 1 of 15 tested products that has this option. You can easly export documenta as 1 file for your factoring. There is many many grest things. POD Complete is free.... Other simular solutions charge 7-25,000$ Down payment and 800-1300 a month. Plus 10-20$ for a driver app.

Cons

Now, yes there is cons, One is sometimes its slogish and it takes a bit to load but not that bad. The other one, POD Complete , well its a little incomplete, it has the options you need, you send the laod and driver can arrive depart, great, attach POD its there but, it needs work, this needs to have transflo options or something like a camsxanner, just to let you cut the page adjust it before you send it over. Plus it would take lot less storage if it was a scan doxument, this way its a picture, not that great for billing, it does work. But I think tailwind shoudl stop all other areas of development cuz they are great and spend some time here, make this app a killer. Evan charge 10$-20$ a driver /mo I would pay it just to get a better app. It needs to have scan features, we all need to get those Bols in good quality, and we dont want to have to use translfo or camscaner or other apps and than have to import the documents into tailwind.

November 2020

Altaf from Sunshine Coast Logistics Inc

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

3.0

Value for money

5.0

Customer support

5.0

Functionality

3.0

November 2020

Powerful Tool for Small to Medium Trucking Operations.

Tailwind is a must have for any trucking company, big or small. Using tailwind has really cut down the amount of time spent each month on administrative tasks. We are looking forward to growing with Tailwind and are excited to see the software evolve.

Pros

The biggest pro for tailwind is its customer service and development team who take your feedback very seriously and are always ready to help you out The software changes every day and if there is a feature or functionality that may not be available, a simple suggestion of yours might just be in the next update. Another pro of the tailwind software is the pricing. When compared to other TMS's, the tailwind system offers the same features of the enterprise and large suite transport systems bundled in an affordable system that you can really customize to fit your needs, and there is no initial setup cost like many other programs. Tailwind also offers free webinars every week for you to either brush up on the software or train a new employee which is very convenient. The system is online based so you are able to access it anywhere and at any time and does not require you to set up a server in your office like many others. One of our favorite features of this software are all the integration, the tailwind team has partnered up with the best service providers (Truckertools, Border Connect,RMIS etc), in the transportation industry to provide an immersed experience when using the software.

Cons

There are not many cons to Tailwind but being an online-based system comes with its negatives as well, and the biggest downfall of the system is that it can be very sluggish at times taking a few seconds to load between screens, and does not fully load the page at times. The software also lacks the ability of end-user customization of documents and the interface. Another con is that the software is mostly designed as a full truckload system and lacks in features for the consolidation of LTL. The accounting portion could use some work as well.

Response from Tailwind Transportation Software

Replied December 2020

Hi Altaf, thanks for the great review! We're glad to hear that Tailwind has helped you reduce the time spent on administrative tasks so you can focus on growing your business!

November 2020

Peter from Profloral Express Ltd.

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

November 2020

Using Tailwind

Great experience. Easy to use and support is at your fingertips with high quality videos tutorials. technical support is very responsive should you require assistance.

Pros

Web based interface with proven stability is a key factor to the Tailwind Product. It does everything you need in terms of a transportation management system.

Cons

No ability to tap into the database and create custom reporting on your own without creating an expensive API.

Reasons for Switching to Tailwind TMS

Gain the ability to track our loads and as well as our drivers. The POD features are important as well.

Response from Tailwind Transportation Software

Replied December 2020

Hi Peter, thank you for the review. Our new Unlimited tier that we launched in September includes API web-hooks which might help.

November 2020

Jane from Sullivan Transportation, Inc.

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 6 months

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

November 2020

Love this Software

We switched our TMS system and had so many problems. Finally, after 4 months we switched to Tailwind...and we have never looked back. It's been nothing but a positive experience! The bottom line is they overpromised and underperformed!

Pros

User friendly. It is very easy to use. And when I can't figure something out, support is right there to help me! It is also affordable!

Cons

Honestly, there is nothing about Tailwind I don't like.

Reasons for Choosing Tailwind TMS

Tailwind seemed to be the one that would most meet our needs.

Reasons for Switching to Tailwind TMS

There are too many problems to list them all. Invoices were never received by customers; paying settlements and payroll was complicated and difficult to be sure of accuracy, and so much more

Response from Tailwind Transportation Software

Replied December 2020

Hi Jane, we appreciate your review!

November 2020

Christie from Legacy Logistics

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

5.0

Customer support

5.0

Functionality

3.0

November 2020

It is a good start to perfect.

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.

Reasons for Switching to Tailwind TMS

We were looking for a program that was more updated and integrated with other programs and apps.

Response from Tailwind Transportation Software

Replied December 2020

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!

November 2020

Genevieve from Micra Transportation Services

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

4.0

Customer support

4.0

Functionality

4.0

November 2020

Could be better

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.

Response from Tailwind Transportation Software

Replied December 2020

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.

November 2020

Tyler from Jackrabbit Logistics LLC

Company Size: 2-10 employees

Industry: Logistics and Supply Chain

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

4.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

November 2020

Great for a new Broker

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.

Reasons for Choosing Tailwind TMS

We are a small office with a limited number of users. We didn't need the multi user accessibility from some of the other more expensive suites and given our existing use of Quickbooks we also didn't need a software at the time of purchase that had a general ledger built in.

Response from Tailwind Transportation Software

Replied December 2020

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!

November 2020

Andrew from Mac Freight

Company Size: 2-10 employees

Industry: Logistics and Supply Chain

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

4.0

Customer support

5.0

Functionality

3.0

November 2020

Day to day operations

Pros

Tailwind for the price is very easy to use, easy to teach and operate.

Cons

Certain small features I wish could be customized. Such as the quantity description. The one option that it does not list which we use all the time is seats or cubes. Another option I would like to see is another check box when a driver is dispatched.

Response from Tailwind Transportation Software

Replied December 2020

Hi Andrew, thanks for sharing your suggestions. As a software that continuously adds enhancements and updates to provide excellent experiences, we appreciate your feedback!

January 2021

Erin from OnDeck Freight Systems

Company Size: 2-10 employees

Industry: Logistics and Supply Chain

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

January 2021

Great support, agile platform.

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.

Response from Tailwind Transportation Software

Replied February 2021

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

September 2019

Devon from D.C. Anderson & Co. LLC

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 12 months

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

September 2019

Awesome software for the small to mid size operation

none, They are fantastic

Pros

Super easy to learn and use. I I am the only one in the office and wear many different hats when it comes to running the company and this software put all the info i need at my fingertips. It is super easy to have an asset based operation and have a brokerage operation and run them on the same screen. It is also super easy to move a load from the one division to another as needed.

Cons

A maintenance module that tracks the service schedule of the equipment would be nice so it is in one package

Reasons for Switching to Tailwind TMS

Desktop based and very unfriendly

December 2020

Cole from Mig, LLC

Company Size: 2-10 employees

Industry: Logistics and Supply Chain

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

December 2020

Great Product

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.

Response from Tailwind Transportation Software

Replied December 2020

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 (support@tailwindtms.com), 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

June 2016

Pamela from Universal Freight & Transportation Inc

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

4.0

Value for money

4.0

Customer support

4.0

Functionality

4.0

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

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

4.0

Value for money

5.0

Customer support

4.0

Functionality

4.0

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.

November 2020

Tim from TOGO DELIVERY

Company Size: 1 employee

Industry: Logistics and Supply Chain

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

4.0

Value for money

4.0

Customer support

3.0

Functionality

5.0

November 2020

Canadian shipping

I dont use a lot of the features offered, because I do most accounting old school.

Pros

produces professional documentation, data base development grows with your company.

Cons

Some edits example adding Trailer types. Can be difficult for us less than computer savvy users

Reasons for Choosing Tailwind TMS

Tailwinds offers me ease of use, Tailwinds is industry recognized.

Reasons for Switching to Tailwind TMS

My own system, development was time consuming.

Response from Tailwind Transportation Software

Replied December 2020

Hi Tim, thanks for your review! It's great to know we can assist you as your company grows, and we are continuously working on ways to make it more and more user friendly and intuitive.

November 2020

Paul from Lenox Logistics

Company Size: 2-10 employees

Industry: Logistics and Supply Chain

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

4.0

Functionality

5.0

November 2020

Tailwinds Is a Game Changer!!!

This has been a great asset to our business and we would not be where we are today without Tailwinds helpiong us with orders/invoices/AP/AR

Pros

We found this programvery user friendly, and having an online based software is amazing, as well as Tailwinds Customer service. They are there for you at a moments notice because of their live chat option.

Cons

Some integrations with QuickBooks can be confusing. But once you get a feel for how the two programs work together it becomes easier

Response from Tailwind Transportation Software

Replied December 2020

Hi Paul, thanks for your review! We are glad you found the software user friendly!

November 2020

Jason from Orangedale Transportation

Verified Reviewer

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

November 2020

Best TMS Software

This software allows us to keep track of shipments, send out rate confirmations and even invoice customers all through the same easy to use application.

Pros

This software is so easy to use and intuitive. It can be used anywhere and has the features that other softwares charge 10+x the amount for.

Cons

Each new device you use the software on, you have to reset the setting, but not something that happens very often. Minimal cons to this software.

Response from Tailwind Transportation Software

Replied December 2020

Hi Jason, thanks for the great review!

January 2019

User Profile Picture

Daniel from Super Shippers

Verified Reviewer

Company Size: 11-50 employees

Industry: Import and Export

Time Used: Less than 12 months

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

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

Replied January 2019

Thanks Daniel - we appreciate the feedback!

December 2020

Ronald from Scott's Transport Limited

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

4.0

Customer support

5.0

Functionality

4.0

December 2020

Overall review - Scotts transport

Overall the Tailwind software has been very easy to use, and trouble free. Tailwind staff as always been quick to respond to any problems and questions that have come up.

Pros

Software is very user friendly, and easy to work with , Implementation into to our organization was very smooth, and trouble free

Cons

would like to see ability to modify data in different modules

Response from Tailwind Transportation Software

Replied December 2020

Hi Ronald, thanks for the feedback, we appreciate it!

November 2020

Katherine from Freight in Motion Brokerage

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 6 months

Review Source: Capterra


Ease-of-use

2.0

Value for money

1.0

Customer support

1.0

Functionality

2.0

November 2020

NOT happy with support!

i am not happy with it. I think it is super expensive for the service we are getting!

Pros

At the beginning I liked the ease of use and the customer service however over the past month, I have been VERY unhappy with the software. *Customer support is AWFUL! I tried to get them to call me over a serious issue and they wouldn't call me back and then another time i had to wait an hour *Issues with printing cheques, this is wasting alot of my time, it is taking me 10 times longer than it did with my previous system

Cons

the "accounting side" of the system, it doesn't work at ALL! customer service

Reasons for Switching to Tailwind TMS

Thought your system had more functions and easier to use but it turns out it does in some areas but others, it's AWFUL!

Response from Tailwind Transportation Software

Replied December 2020

Hi Katherine, I'm disappointed to hear about the apparent poor service you report to have received from Tailwind. We do really pride ourselves on providing prompt and full support - which is why we keep it in-house rather than offshoring. I have reviewed the latest set of conversations you have had with the Tailwind Support team, and it appears that a solution for your issues has been found (and thank you for the latest 'Amazing' conversation rating you provided!). That said - our goal at Tailwind is to provide you with a transportation management system that will allow you grow your business - and ideally, give you a bit more time at the end of your day) - so if you do require additional support - please do reach out (support@tailwindtms.com; 1-866-441-0441).

November 2020

Jeff from LOTUS TERMINALS

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

3.0

Customer support

4.0

Functionality

3.0

November 2020

Tailwind Review

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.

Response from Tailwind Transportation Software

Replied December 2020

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

June 2016

JOHN from ATS Canada

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

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.

December 2020

Jack from Irish Transport

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

December 2020

Irish Review

I have been very pleased with Tailwind. Overall it is very user friendly and the staff is very responsive when I am needing assistance. It has all the features that we need as a 3PL user.

Pros

User Friendly, Integrations, adapting to our needs.

Cons

Quickbooks implementation, Speed of software at times.

Response from Tailwind Transportation Software

Replied December 2020

Hi Jack, thanks for your review! We're glad to assist you!

November 2020

Andrew from DRT Transportation

Company Size: 51-200 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

4.0

Value for money

5.0

Customer support

5.0

Functionality

4.0

November 2020

Good value for money

If you are on the go all the time, since Tailwind is web based, you can login on your laptop when on the road. Tailwind offers a paperless environment.

Pros

I like the fact that we can use multiple currency. This makes it easy to do business with both American and Canadian customers

Cons

When you create a LTL shipment with different skid dimensions, you are unable to input the different sizes

Reasons for Choosing Tailwind TMS

Good product, good customer support.

Response from Tailwind Transportation Software

Replied December 2020

Hi Andrew, thank you for taking the time to leave us a review!

November 2020

Angie from Blanchette Transportation Services

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

4.0

Customer support

5.0

Functionality

5.0

November 2020

Very happy with Tailwind and their customer service

We love the software and the staff if awesome to work with

Pros

It’s internet based which has made it very easy to go anywhere and still be able to work

Cons

There is a few extra steps when importing to Quick Books

Response from Tailwind Transportation Software

Replied December 2020

Hi Angie, thanks for your review! Great to hear that you're using the software where-ever you need to be!

November 2020

Carmine from TCB Logistics LLC

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

4.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

November 2020

Tailwind TMS Performs

VERY GOOD experience overall. I won't even look at others for now.

Pros

Easy to install, easy to use, great customer service.

Cons

Making changes to dispatches. Has to be done in multiple places.

Response from Tailwind Transportation Software

Replied December 2020

Hi Carmine, thanks for the review and feedback, we hope you continue to have a good experience with the software!

November 2020

Sheila from DC Anderson & CO, LLC

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Customer support

5.0

Functionality

5.0

November 2020

Tailwind TMS

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.

Response from Tailwind Transportation Software

Replied December 2020

Hi Sheila, thank you for the review!

December 2020

kevin from RLS Global, Inc.

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: More than 2 years

Review Source: Capterra


Ease-of-use

5.0

Customer support

5.0

Functionality

4.0

December 2020

Tailwind review

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.

Response from Tailwind Transportation Software

Replied December 2020

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

April 2018

Daniel from Naked Lady Trucking LLC

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 6 months

Review Source: Capterra


Ease-of-use

4.0

Value for money

4.0

Customer support

5.0

Functionality

5.0

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

Industry: Transportation/Trucking/Railroad

Time Used: Less than 6 months

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

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.

November 2020

Ricky from Lotus Terminals Ltd.

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

4.0

Value for money

5.0

Customer support

4.0

Functionality

4.0

November 2020

Review

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.

Reasons for Choosing Tailwind TMS

Ease of use

Response from Tailwind Transportation Software

Replied December 2020

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

November 2020

Al from Multi-National Logistics Inc.

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

4.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

November 2020

Great Software

Very good software

Pros

Ease of use and that we can access from anywhere - web based

Cons

Processing deposits - When crediting short pays or over payments.

Reasons for Switching to Tailwind TMS

Looking for a web based program

Response from Tailwind Transportation Software

Replied December 2020

Hi Al, thanks for taking the time to leave us a review and feedback!

November 2020

GURPREET from SARTAJTRUCKING LTD

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

3.0

Value for money

4.0

Customer support

5.0

Functionality

4.0

November 2020

Best software

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

Response from Tailwind Transportation Software

Replied December 2020

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

November 2020

Lovepreet from FASTLANE FREIGHT SYSTEMS INC

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 12 months

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

November 2020

Review

Pros

I like how easy it is to use the software, easy to navigate.

Cons

Sometimes the software is really slow and I have to reload a lot

Response from Tailwind Transportation Software

Replied December 2020

Hi Lovepreet, thanks for your review and the feedback! We are sorry to hear you are having to reload the software at times. We are always updating our software to provide the best experience for our customers. Your issues have been brought to the attention of the development team to ensure adjustments will be made.

December 2018

Simon from Ready Freight Ltd

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 6 months

Review Source: Capterra


Ease-of-use

5.0

Value for money

4.0

Customer support

5.0

Functionality

4.0

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

Industry: Transportation/Trucking/Railroad

Time Used: Free Trial

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

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 2019

Scott from O'Brien Logistics

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 12 months

Review Source: Capterra


Ease-of-use

2.0

Value for money

2.0

Customer support

2.0

Functionality

5.0

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

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.

March 2016

Kevin from Target Transportation Ltd

Time Used: Free Trial

Review Source: Capterra


Ease-of-use

5.0

Customer support

5.0

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."

November 2020

Jordan from Rouge river trans

Company Size: 51-200 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

1.0

Value for money

3.0

Customer support

3.0

Functionality

2.0

November 2020

Too many clicks

If this change was made it would be excellent software but until then it takes way to many clicks and to much time to build loads.

Pros

Not sure. It needs to be made more efficient.

Cons

Creating a shipment. Way to many windows and clicks. There should be one window to add in POs etc not several different. It consumes a lot more time than needed. I’ve mentioned this to support before but they didn’t seem to care

Reasons for Choosing Tailwind TMS

Not sure

Response from Tailwind Transportation Software

Replied December 2020

Hi Jordan, we appreciate your feedback! We are continuously looking to improve and produce quality software for our customers. We take pride in providing exceptional customer service and support so we will be reviewing the interactions you had with our team.

January 2017

steve from XLG Transportation Inc

Company Size: 11-50 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 6 months

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

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

Industry: Transportation/Trucking/Railroad

Time Used: Less than 6 months

Review Source: Capterra


Ease-of-use

5.0

Value for money

5.0

Customer support

5.0

Functionality

5.0

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.

Time Used: Free Trial

Review Source: Capterra


Ease-of-use

4.0

Customer support

5.0

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.

November 2020

Dannielle from shaans Trucking ltd

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 12 months

Review Source: Capterra


Ease-of-use

4.0

Value for money

3.0

Customer support

4.0

Functionality

4.0

November 2020

Small Business Solution

Pros

Dispatching side of things, ease of use when dispatching drivers

Cons

Accounting side is not a diversified as I would like

Response from Tailwind Transportation Software

Replied December 2020

Hi Dannielle, we appreciate your feedback and review!

June 2016

Gretchen from Reliable Source Logistics

Time Used: Free Trial

Review Source: Capterra


Ease-of-use

5.0

Customer support

5.0

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

December 2020

Brian from B & M TRANSPORTATION, INC

Company Size: 2-10 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

1.0

Value for money

2.0

Customer support

5.0

Functionality

4.0

December 2020

Usage

Pros

I used the old version, much more user friendly. This package is very difficult to use.

Cons

not user friendly, too many obstacles at every corner.

Reasons for Choosing Tailwind TMS

Used it at another brokerage, (old version). This new version is bad

Response from Tailwind Transportation Software

Replied December 2020

Hi Brian, thanks, the feedback! We're sorry to hear you're having troubles switching from the on-premise to online Tailwind TMS. While switching to a new system is rarely easy, we do offer in-app support, free online training sessions and demos, and even free 1-1 'health-checks' to make sure you're able to get the most of the software.

April 2019

Ashley from Acanela Expeditions

Company Size: 11-50 employees

Industry: Hospitality

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

5.0

Value for money

4.0

Customer support

5.0

Functionality

4.0

April 2019

Helpful Pinterest Support

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.

November 2020

Aaron from Rouge RIver Transporation

Company Size: 501-1,000 employees

Industry: Transportation/Trucking/Railroad

Time Used: Less than 2 years

Review Source: Capterra


Ease-of-use

1.0

Value for money

5.0

Customer support

4.0

Functionality

1.0

November 2020

Rouge River Trans Aaron

Its not horrible but i wouldn't recommend

Pros

software can use from any computer pretty inexpensive no upfront fee

Cons

to many steps to do simple task ( copy orders) wont let you set a new pickup number or customer order number from copy screen) runs very slow for no reason

Reasons for Switching to Tailwind TMS

wanted cloud

Response from Tailwind Transportation Software

Replied December 2020

Hi Aaronwe're continuously updating the software to ensure it speeds up user workflows so appreciate your feedback!

February 2016

Roxanne from California Specialized Equipment Systems, Inc

Time Used: Free Trial

Review Source: Capterra


Ease-of-use

5.0

Customer support

5.0

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.

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