App comparison

Add up to 4 apps below to see how they compare. You can also use the "Compare" buttons while browsing.

Software categories Blog & research About us

GetApp offers objective, independent research and verified user reviews. We may earn a referral fee when you visit a vendor through our links.

Our commitment

Independent research methodology

Our researchers use a mix of verified reviews, independent research, and objective methodologies to bring you selection and ranking information you can trust. While we may earn a referral fee when you visit a provider through our links or speak to an advisor, this has no influence on our research or methodology.

Learn more

Verified user reviews

GetApp maintains a proprietary database of millions of in-depth, verified user reviews across thousands of products in hundreds of software categories. Our data scientists apply advanced modeling techniques to identify key insights about products based on those reviews. We may also share aggregated ratings and select excerpts from those reviews throughout our site.

Our human moderators verify that reviewers are real people and that reviews are authentic. They use leading tech to analyze text quality and to detect plagiarism and generative AI.

Learn more

How GetApp ensures transparency

GetApp lists all providers across its website—not just those that pay us—so that users can make informed purchase decisions. GetApp is free for users. Software providers pay us for sponsored profiles to receive web traffic and sales opportunities. Sponsored profiles include a link-out icon that takes users to the provider’s website.

Learn more

Tailwind TMS

Web-based trucking & freight broker software for SMBs

Table of Contents

Is this product right for your business?

Find out with a

Tailwind TMS - 2026 Pricing, Features, Reviews & Alternatives

All user reviews are verified by in-house moderators and provider data by our software research team. Learn more

Last updated: March 2026

Tailwind TMS overview

What is Tailwind TMS?

Tailwind is a true web-based trucking and freight broker software, catering to small and mid-sized trucking businesses, freight brokerages, and businesses that do both. There are no up-front fees associated with this Transportation Management System (TMS), and you can start with a free trial.

Tailwind is offered in three-tiers. Tailwind Pro costs $99 user/month, and Tailwind Enterprise - $149 user/month, and Tailwind Unlimited, $199 user/month. Each level includes integration with QuickBooks Online, and a free mobile ePOD capture and dispatch communications app (Tailwind POD Complete) for all drivers associated with a business' subscription.

Tailwind Pro offers features such as operations and accounting, sales tracking , carrier rate history maintenance. It also supports multi-offices and multi-division businesses. It allows clients to track mileage, claims, incidents and accidents. Clients can also access multiple load boards and post their freight or equipment to get new customers and orders.

Tailwind Enterprise is a more robust offering which supports integration with various third-party transportation services and includes additional features such as Customer and Carrier Portals which give companies the ability to provide more self-serve options for their customers and partners.

Tailwind Unlimited TMS is built to provide unlimited visibility into your shipping events, unlimited business intelligence insights, unlimited technology integrations, and EDI. It includes an even greater number of integrations (ie: for Carrier Onboarding, Business Intelligence platforms) as well as API Web-hooks to allow for companies to perform 'self-serve' integrations.

Starting price

99per user /
per month

Alternatives

with better value for money

Pros & Cons

Customer Support

Invoicing

Training and Learning Curve

Driver Management

Customizability

Accounting and Tracking

Tailwind TMS’s user interface

Ease of use rating:

4.2

(97)

Tailwind TMS pros, cons and reviews insights

To determine these pros and cons insights, we analyzed responses from

Overall rating

Reviews sentiment

1-2(6)

3-4(41)

5(50)

What do users say about Tailwind TMS?

Many others do the same thing for far less, and with better customer service.

Select to learn more

Who uses Tailwind TMS?

Based on 97 verified user reviews.

Company size

Small Businesses

Midsize Businesses

Enterprises

Top industries

Transportation/Trucking/Railroad

Logistics and Supply Chain

Use cases

Transportation Dispatch

Transportation Management

Logistics

Freight

Trucking

Tailwind TMS's key features

Most critical features, based on insights from Tailwind TMS users:

Fleet management

5.0

(1)

Order management

3.6

(5)

Customer management

4.5

(2)

Billing & invoicing

4.3

(4)

Scheduling

3.7

(3)

Routing

(0)

Dispatch management

3.0

(1)

Live driver tracking

5.0

(1)

All Tailwind TMS features

Features rating:

4.0

(97)

3PL management

4.7

(3)

Accounting

4.0

(2)

API

(0)

Billing & invoicing

4.3

(4)

Carrier management

4.0

(1)

Communication management

(0)

Contact database

3.0

(2)

CRM

5.0

(1)

Customer database

(0)

Customer management

4.5

(2)

Customer portal

(0)

Data import/export

(0)

Dispatch management

3.0

(1)

Driver management

3.0

(1)

Driver settlements

5.0

(1)

EDI

(0)

Fleet management

5.0

(1)

For freight operations

(0)

Fuel management

(0)

GPS

3.0

(1)

Historical reporting

(0)

Import/Export management

(0)

International forwarders

(0)

Live driver tracking

5.0

(1)

Load optimization

(0)

Local forwarders

(0)

LTL/Shared truckload

(0)

Maintenance management

(0)

Maintenance scheduling

(0)

Mileage tracking

5.0

(1)

Mobile app

(0)

Order management

3.6

(5)

Order tracking

(0)

QuickBooks integration

(0)

Quotes/Estimates

3.0

(1)

Rate management

(0)

Real-Time notifications

(0)

Reporting/Analytics

(0)

Route Management

(0)

Routing

(0)

Scheduling

3.7

(3)

Shipment tracking

3.0

(2)

Third-Party integrations

5.0

(1)

Transportation management

3.3

(3)

Trip logs

(0)

Truckload management

3.0

(1)

Vehicle management

3.0

(1)

Waybills

3.0

(1)

Tailwind TMS alternatives

Tailwind TMS

4.2

(97)

Starting from

/user

Per month

Free trial

Free version

Ease of Use

4.2

Features

4.0

Value for Money

4.2

Customer Support

4.5

Samsara

4.5

(967)

learn more

Starting from

No pricing info

Free trial

Free version

Ease of Use

4.5

Features

4.4

Value for Money

4.3

Customer Support

4.2

Motive

4.5

(1.6K)

learn more

Starting from

No pricing info

Free trial

Free version

Ease of Use

4.4

Features

4.4

Value for Money

4.2

Customer Support

4.4

One Step GPS

4.8

(262)

learn more

Starting from

13.95

Per month

Free trial

Free version

Ease of Use

4.9

Features

4.7

Value for Money

4.8

Customer Support

4.8

Tailwind TMS pricing

Value for money rating:

4.2

Pricing plans

Pricing details:

Free plan

Free trial

Subscription

Pro

/user

Per month

Features included:

25 Loads/Month GPS Confirmed Shipment and Event Tracking
Accounting & Operations Report
Account Receivable Management
Accounts Payable Management
Admin
Businner Document Customization
Claims.Accident/Incident Tracking
Complete Quote and Order System
Customer and Carrier History
Customer and Vendor Database
Custom User Security
Direct Emailing From TMS
Dispatch and Shipment Tracking System
Equipment Maintenance Tracking
Factor Support
Fuel Bill Importing
Location and Route Management
Macropoint Shipment Tracking Integration
Mileage Calculations
Multi-Branch Management
POD Import and Attach
Print Checks Right From the TMS
Quickbooks Online Sync
Saferwatch FMCSA Data Feed
Sales Commission System
Support US and CDN Currencies
Task and Alert Notification System

Enterprise

149

/user

Per month

Features included:

50 Loads/Month GPS Confirmed Shipment and Event Tracking
API Access for Tailwind Supported Integrations
Carrier Self-Service Portal
Customer Self-Service Portal
Electric Load/ Rate Confirmation and Acceptance
Samsara ELD Integration

Unlimited

199

/user

Per month

Features included:

API Web-Hooks for Self-Serve Integrations
Custom Reporting and Analytics With Power BI Integration
Easy Carrier Onboarding With RIMS Integration
Unlimited Loads GPS Confirmed Shipment and Event Tracking

User opinions about Tailwind TMS price and value

Value for money rating:

4.2

(97)

To see what individual users think of Tailwind TMS's price and value, check out the review snippets below.

“Easy to find an order and create a dispatch and save the POD and BOL and enter the cost associated with the load”

Ashveen K.

Dispatcher

“Many others do the same thing for far less, and with better customer service.”

Mario B.

Operations Manager

Tailwind TMS integrations (6)

Integrations rated by users

We looked at 97 user reviews to identify which products are mentioned as Tailwind TMS integrations and how users feel about them.

QuickBooks Online

Integration rating: 5.0 (2)

“quickbooks is where I did all my bookkeeping. was a little clunky to send the balance invoice via honeybook because there was no way to differentiate products and services, which is why i took off one star.”

Sarah D.

CEO

Other top integrations

QuickBooks Online Advanced

Tailwind TMS customer support

What do users say about Tailwind TMS customer support?

Customer support rating:

4.5

We analyzed verified user reviews to identify positive and negative aspects of Tailwind TMS customer support.

The majority of users highlight fast, responsive support via phone, chat, and email, with issues often resolved quickly and efficiently.

A significant portion of users appreciate knowledgeable staff who explain solutions clearly and provide hands-on help during onboarding and troubleshooting.

Select users report recent declines in support quality, citing difficulties reaching live agents and frustration with portal-based ticketing.

Support options

Knowledge base

Email/help desk

Chat

Phone support

Faqs/forum

24/7 (live rep)

Training options

Videos

Live online

Webinars