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 ...


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Supported Operating System(s):

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

65 Reviews of Tailwind Transportation

Average User Ratings

Overall

4.48 / 5 stars

Ease-of-use

4.5

Value for money

4.5

Customer support

4.5

Functionality

4.5

Ratings Snapshot

5 stars

(40)

40

4 stars

(17)

17

3 stars

(7)

7

2 stars

(1)

1

1 stars

(0)

0

Likelihood to Recommend

Not likely

Very likely

Showing 1 - 5 of 65 results

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 Transportation

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

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.

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 Transportation

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.

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.