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Tailwind TMS
Based on GetApp‘s extensive, proprietary database of in-depth, verified user reviews
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
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.
Key benefits of using Tailwind TMS
• The solution integrates with various key technologies in the trucking industry such as load boards, mileage, accounting and fuel supply.
• The Tailwind TMS allows your business to transmit, fax, email, and scan documents from the same solution.
• The product is integrated with Here.com for route and load optimization.
• With Tailwind's web tracking module, clients can post their freight brokerage on multiple load boards such as Post Everywhere, DAT Solutions, Truckstop.com, and can connect with new customers.
Starting price
per month
Alternatives
with better value for money
Tailwind TMS’s user interface
Tailwind TMS pros, cons and reviews insights
To determine these pros and cons insights, we analyzed responses from
Overall rating
Value for money
4.2
Features
4.0
Ease of use
4.2
Customer support
4.5
Reviews sentiment
What do users say about Tailwind TMS?
Reviewers appreciate Tailwind TMS for its responsive customer support, with many noting quick solutions via chat or phone and helpful guidance during onboarding and troubleshooting. They feel the support team explains features clearly, though some mention frustrations with recent changes to service channels and inconsistent follow-up on requests.
Users think Tailwind TMS is easy to learn and use, highlighting intuitive navigation, straightforward training resources, and accessible tutorials. They report that accounting and load tracking are generally efficient, but some find the accounting features less robust and wish for better integration with external platforms.
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Who uses Tailwind TMS?
Based on 97 verified user reviews.
Company size
Small Businesses
Enterprises
Midsize Businesses
Top industries
Use cases
Tailwind TMS's key features
Most critical features, based on insights from Tailwind TMS users:
All Tailwind TMS features
Features rating:
Tailwind TMS alternatives
Tailwind TMS
Starting from
99
/user
Per month
Freightview
Starting from
149
Per month
Transvirtual
Starting from
No pricing info
Easy4Pro
Starting from
No pricing info
Tailwind TMS pricing
Pricing plans
Pricing details:
User opinions about Tailwind TMS price and value
Value for money rating:
To see what individual users think of Tailwind TMS's price and value, check out the review snippets below.
Pamela L.
Gen Mgr
Paul K.
Office Manager
Tailwind TMS integrations (10)
Tailwind TMS support options
Typical customers
Platforms supported
Support options
Training options
Tailwind TMS FAQs
Tailwind TMS has the following pricing plans:
Starting from: $99.00/month
Pricing model: Subscription
Free Trial: Available
These products have better value for money
Q. Who are the typical users of Tailwind TMS?
Tailwind TMS has the following typical customers:
Freelancers, Large Enterprises, Mid Size Business, Small Business
Q. What languages does Tailwind TMS support?
Tailwind TMS supports the following languages:
English
Q. Does Tailwind TMS support mobile devices?
Tailwind TMS supports the following devices:
Android, iPad, iPhone
Q. Does Tailwind TMS offer an API?
Yes, Tailwind TMS has an API available for use.
Q. What other apps does Tailwind TMS integrate with?
Tailwind TMS integrates with the following applications:
QuickBooks Online Advanced, EZTrack, Descartes MacroPoint, EZCheck-In, Google Maps, Samsara
Q. What level of support does Tailwind TMS offer?
Tailwind TMS offers the following support options:
Knowledge Base, Email/Help Desk, Chat, Phone Support, FAQs/Forum, 24/7 (Live rep)
