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

47 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

(30)

30

4 stars

(13)

13

3 stars

(3)

3

2 stars

(1)

1

1 stars

(0)

0

Likelihood to Recommend

Not likely

Very likely

Showing 1 - 5 of 47 results

March 2018

Jason from Orangedale Transportation

Verified Reviewer

Industry: Transportation/Trucking/Railroad

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

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).

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

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.

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.