Tailwind TMS Trucking Review: Features & Pricing 2023

Mark has researched and reviewed accounting software at Fit Small Business since 2019 and has developed an extensive knowledge of accounting software features and how unique business needs determine the best accounting software.

Tim is a Certified QuickBooks Time (formerly TSheets) Pro, QuickBooks ProAdvisor, and CPA with 25 years of experience. He brings his expertise to Fit Small Business’s accounting content.

Tailwind TMS by Envase is a cloud-based transportation management system (TMS) with integrated basic accounting functions such as accounts payable (A/P) and accounts receivable (A/R). It’s designed to help trucking companies and freight brokerages manage their operations, customers, dispatch processes, and accounting workflows. Tailwind TMS offers three subscription levels, with prices that start at $117 per user, per month. All plans come with a free trial.

Tailwind logo.Tailwind logo.

Overall Score:

3.70

/ 5

RATING CRITERIA

Pricing

3.50

/ 5

General Accounting

2.40

/ 5

Trucking-specific Features

5.00

/ 5

Ease of Use & Customer Support

3.6 0

/ 5

User Reviews

4.30

/ 5

Pros

  • Packed with many trucking management features like order and dispatch management
  • Syncs with QuickBooks Online and QuickBooks Desktop (depending on subscription)
  • Includes a Fuel Import tool to automatically record fuel expenses
  • GPS-confirmed shipment and event tracking
  • Multiple branch/division management capability

Cons

  • Payroll unavailable
  • Not a full-fledged accounting software
  • Bank reconciliation feature unavailable
  • Limited number of loads to track in the low-tier plans
  • Can’t use free trial right away; need to complete a form and wait for email verification

  • Freight brokers working with many vendors and customers: Tailwind TMS is our choice for the best trucking accounting software for businesses that need strong invoicing and bill payment software with built-in trucking features. All plans allow you to send an unlimited number of invoices and pay as many vendors as needed.
  • Logistics companies with trucking assets and broker loads: The carrier management feature lets you manage and track dispatch information, including available loads, shipments that have been dispatched, and current and past-due payables.
  • QuickBooks users that want a trucking integration: Tailwind TMS provides trucking company features as an addition to QuickBooks accounting. Setting it up and syncing your data is relatively seamless, and Tailwind TMS can assist you with any issues. QuickBooks Online Plus integrates with any plan while QuickBooks Desktop integrates with the Enterprise and Unlimited plans.
  • Large trucking companies managing 20 to 100 trucks: Tailwind TMS’s Unlimited package allows you to track an unlimited number of shipments per month.

  • Trucking companies that need a complete bookkeeping system: While Tailwind TMS can perform basic A/R and A/P tasks, it isn’t possible to reconcile bank accounts or perform full double-entry accounting. If you need a complete bookkeeping solution, we recommend QuickBooks Online. If you want a complete trucking solution, you can integrate Tailwind TMS with QuickBooks Online to create a powerful package.
  • Trucking companies dealing with internet connectivity issues: Tailwind is completely cloud-based, which means it needs an internet connection to run. If you’re having problems with internet connection and speed, you might want to try Q7, which has cloud- and desktop-based versions.
  • Small trucking companies that want easy and affordable International Fuel Tax Agreement (IFTA) tracking: If you’re mainly looking for an affordable way to maintain IFTA compliance, Rigbooks is an excellent option that also provides inexpensive management software.

Visit Tailwind TMS

Are you looking for something else? If you think general bookkeeping software might meet your trucking company’s needs, check out our roundup of the best small business accounting software.

Tailwind TMS Deciding Factors

Supported Business Types

Small and medium-sized motor carriers and trucking and freight brokerage companies

Pricing

  • Pro: $117 per user, per month
  • Enterprise: $176 per user, per month
  • Unlimited: $235 per user, per month

Free Trial

30 days

Standout Features

  • Allows you to manage your A/P and A/R
  • Helps you track dispatch information easily, such as dispatched shipments and the number of loads available
  • Enables you to create and track customer orders and set up basic freight charges or fuel surcharges
  • Includes a self-service portal for carriers and customers
  • Lets you run accounting, admin, and operation reports

User Reviews

4.32 out of 5 based on around 100 reviews on Software Advice

Customer Support

Phone and email support, customer support packages, on-demand training videos, and self-help guides like blogs and set-up guides

Tailwind TMS Alternatives

Tailwind TMS vs Competitors

Tailwind TMS may check off many boxes in a trucking management system, but it’s not a complete solution. To help you decide between Tailwind TMS and top alternatives, we compared it with QuickBooks Online and Rigbooks.

Based on the chart below, Tailwind TMS and Rigbooks are equally great at trucking management. However, if you want an affordable solution, you should consider Rigbooks, which costs as little as $19 per month. If you only need basic accounting with no specialized trucking management features, then try QuickBooks Online. You may also consider integrating QuickBooks with Tailwind TMS to develop a powerful bookkeeping and trucking management solution combined.

Tailwind TMS vs Competitors FSB Case Study

Touch the graph above to interact
Click on the graphs above to interact

  • Tailwind TMS
    From $117 per month Secondary Series (More faded, in the background, than the primary series)

  • QuickBooks Online
    From $30 per month

  • Rigbooks
    From $19 per month

Tailwind TMS Trucking Pricing

3.50
/

5

Tailwind TMS is available in three packages with prices that range from $117 to $235 per month. Below is a brief comparison of the Tailwind TMS plans in terms of pricing and features.

 

Pro

Enterprise

Unlimited

Monthly Billing ($/User/Month)

$117

$176

$235

Annual Billing ($/User/Month)

$99

$149

$199

Assisted Onboarding (Optional)

25

50

Unlimited

GPS Confirmed Shipment & Event Tracking (Maximum Loads Per Month)

A/P & A/R Management

Admin, Accounting & Operation Reports

Business Document Customization

Dispatch & Shipment Tracking System

Driver/Carrier Settlement

Mileage Calculations

Equipment Maintenance Tracking

QuickBooks Online Sync

Electronic Load/Rate Confirmation & Acceptance

Carrier Self-service Portal

QuickBooks Desktop Integration

Custom Reporting & Analytic

Easy Carrier Onboarding With Registry Monitoring Insurance Services (RMIS) Integration

Electronic Data Interchange (EDI) Integration

For a complete comparison of the Tailwind TMS plans, visit the provider’s pricing page.

Whether you need help to migrate your files, set up and customize your new Tailwind TMS platform, or sync your data between Tailwind and QuickBooks, you can sign up for a paid TMS-assisted implementation service.

Quick Start

QuickBooks Config

Sure Start

Accelerator

One-time Fee

$0

$199

$399

$999

Implementation Checklist

Access to Online Group Training

Access to Self-help Documents & Video Training Modules

Data Import Assistance

Initial Sync Between Tailwind TMS & QuickBooks

Tailwind TMS & QuickBooks Complete Mapping and Configuration

One-hour Training for Administrator

One-hour Orientation for Users

Client Portal Configuration Assistance

Mobile App Configuration Assistance

Ability to Include Your Brand in Your Documents

Two Basic Document Customizations

Step-by-Step Implementation Plan

Weekly Implementation Review Calls

QuickBooks Configuration

Tailwind TMS Features

General Accounting Features

2.40
/

5

Tailwind TMS didn’t do well in general accounting because it’s not a full double-entry accounting system and therefore lacks some essential features. For instance, it doesn’t allow you to connect your bank account and perform bank reconciliation. However, it still has decent accounting features, which we’ll explore below.

The A/R module allows you to create and send invoices to your clients and even print them if needed. Once an order is completed, administrators will be notified and can easily send the invoice from the Invoice list. The invoice list displays all orders that are completed but not yet posted.

To process the invoice, select the invoice from the list and click on the Approved toggle on the left side of the invoice entry. If you wish to review the invoice details before sending, simply click the blue “〇” button next to the toggle button.

Invoice list screen where you can select invoice to process in Tailwind TMS.Invoice list screen where you can select invoice to process in Tailwind TMS.

After selecting the invoice to process, there are three ways to proceed:

  1. Transmit Only: Print, email, or send a copy of the invoice electronically.
  2. Post Only: Post the invoice without printing it.
  3. Transmit & Post: Print or send a copy of the invoice and then post all checked orders.

When you post an invoice, Tailwind TMS will create an entry in the Receivables list, waiting for payment from your customer. If you post an invoice without transmitting it, then make sure to send the customer through another channel.

When an order is completed, all expenses associated with that order will show up in the Bill Posting module, just like how invoices appear on the Invoices List. While you can post the invoice along with the related bills, you can post a bill separately, particularly if it’s not associated with an order—whether it’s an office expense or employee wage.

To create a new standalone bill, go to the Payables list and then click on the Create button to bring up the Create Bill page.

Screen where you can record a new bill in Tailwind TMS.Screen where you can record a new bill in Tailwind TMS.

On the Create Bill screen, you must provide the necessary details, such as the appropriate bill type, the vendor, and the bill date.

You can also see the bills waiting to be posted from the Bill Posting module. These bills include those from completed orders and those that have been recorded as standalone bills. To review or edit the bill details, click on the blue “〇” button, and if you wish to post the bill, click on the Post button on the top of the screen.

Bill Posting module in Tailwind TMS showing bills waiting to be posted.Bill Posting module in Tailwind TMS showing bills waiting to be posted.

While it’s not possible to prepare a balance sheet, you can run profit and loss (P&L) statements and A/P and A/R aging reports in Tailwind TMS. A/P aging reports help you better visualize the amounts you owe to your vendors while A/R aging reports let you track outstanding invoices and the length of time an invoice is past due.

Trucking-specific Features

5.00
/

5

Tailwind TMS has all the trucking management features we wanted to see, including dispatch and order management, fuel and mileage tracking, equipment maintenance, and IFTA tracking and reporting.

Tailwind TMS allows you to create orders for your customers, representing where the load is picked up and delivered to. It also allows you to charge customers basic freight charges or fuel surcharges. You can also track sales commissions, carrier partner pay, and company driver pay by the mile, by the hour, or by owner-operator revenue splitting.

Tailwind TMS’s design allows for a wide variety of approaches to moving cargo. Whether you have a customer that needs multiple shipments delivered simultaneously, needs to swap carriers midroute, or has any other variation, the software can assist you with keeping everything on track.

You and your customers will receive email notifications alerting you when a load has been picked up or delivered. You can also copy an existing order for customers that always want the same shipment delivered so that you don’t have to enter the same information repeatedly.

To create a new order in Tailwind TMS, go to the Orders list and click on the Create button. The Order Creation table shows up, asking you to select the customer you’re creating the order for. You’ll also need to provide shipment details and revenue lines.

Screen where you can create a new order in Tailwind TMS.Screen where you can create a new order in Tailwind TMS.

For trucking companies, it’s essential to keep track of their equipment, such as tractors and trailers. Tailwind TMS provides the tools you need to manage and maintain your equipment, including the ability to track its location, who’s using them, and when they need maintenance. You can view the list of your equipment records from the Equipment List menu. To add a new equipment record, simply create on the Create Equipment button, and complete the Create Equipment form as shown below.

Screen where you can add a new equipment record in Tailwind TMS.Screen where you can add a new equipment record in Tailwind TMS.

Some of the fields you need to complete include the unit type, owner, certification information, weights and measurements, and purchase details. Once you have provided all the necessary details, click the Create button to finish.

Tailwind’s Fuel Import tool allows you to import fuel invoices directly from vendors into the system instead of entering them manually. The tool generates a bill automatically for the fuel vendor, while also recording fuel stops to your equipment records. However, note that before you can use the Fuel Import tool, you need to set up fuel expense items to allocate your costs and related items, such as fuel, cash advance, oil and additives, fuel transaction fee, and fuel rebates.

Small and midsized shipping companies rarely have enough staff to stay on top of all of their personnel and equipment compliance issues. Tailwind TMS allows you to store compliance details in specific records.

When you set up your company drivers or owner-operator drivers, you can track compliance details, such as Hazmat certificates, the expiration of medical exams, and the last time you did an annual driver record review. It also tracks commercial driver’s licenses and their related expiration dates.

You also can track all compliances on equipment records like safety inspections or IFTA renewal dates. You can even keep comprehensive preventative maintenance schedules for the servicing of your vehicles. The software will remind you automatically when a compliance item is due, helping you to avoid costly violations.

The Enterprise and Unlimited subscription plans allow you to set up a self-service portal for your customers and carriers. The Customer portal grants your customers access to information about their accounts, shipments, and invoices. They can also use the portal to request quotes or even place orders directly, which saves you time.

The Carrier portal is a tool that allows your carriers to have limited visibility into the parts of your Tailwind TMS database that directly relate to your business with them: available loads, shipments you have dispatched, and information regarding current and past-due payables. This allows for quicker and more efficient communication between you and your carriers.

 Customer portal in Tailwind TMS showing shipment status. Customer portal in Tailwind TMS showing shipment status.

Tailwind TMS can act as a customer relationship management (CRM) platform for your business. It allows you to track your customers, keep comprehensive credit information, and make notes as to when sales calls were made. You can generate a customized report that summarizes this data for review.

Screenshot of Tailwind TMS Customer List.Screenshot of Tailwind TMS Customer List.

Tailwind TMS helps you manage orders, invoicing, and receivables. You can capture and manage shipper and shipment details, such as appointment times and pick-up and delivery windows, quickly and easily. You can also pull information from orders to create dispatches, or create a standalone dispatch, and choose a carrier partner to move the load.

Once a dispatch is created, you can send a trip manifest to your driver’s cellphone. If you’re using a carrier partner, you can send an electronic load confirmation to them with pickup city, delivery city, and rate details.

You can find the order you wish to dispatch from the Order List, shown below.

Order list in Tailwind TMS.Order list in Tailwind TMS.

Preconfigured reports allow you to quickly see the overall health of your business and which customers are most profitable. There are more than 40 built-in reports which give you the ability to measure key performance indicators (KPIs) easily. These include a variety of administrative, sales, operations, and equipment reports. There is also an option to use advanced search to apply multiple filter parameters, which gives you the flexibility to pull the reports you need.

Here are some examples of available reports:

  • Administrative: A/R Aging Summary, A/P Aging Summary, Trial Balance, Transaction List by Customer, and Expense Item Summary
  • Sales: Revenue by Sales Rep Detail, Profit by Account Rep Detail, Profit by Invoice, Number Loads Per Account Rep, and Number Loads by Sales Rep
  • Operations: Profit by Customer Detail, Profit by Trip, Quote to Order Percent, Driver Miles, and Bill of Lading Details
  • Equipment: Miles Per Truck Detail, Shipment Delivery Dates, Fuel Per Mile, Fuel Purchased by State, and Revenue Per Mile

2.8

Star ratings 2.5Star ratings 2.5

On App Store

3.7

Star ratings 3.5Star ratings 3.5

On Google Play

The Tailwind POD Complete mobile app is a great tool for drivers, as it allows them to capture a signed bill of lading with their mobile phone at the point of delivery (POD). The app is available for both iPhones and Androids and is included for free with a Pro or Enterprise subscription.

Tailwind TMS Ease of Use & Customer Support

3.60
/

5

Tailwind TMS is fairly easy to use, but it has no live chat support and doesn’t offer assisted bookkeeping. We believe live chat support is a convenient channel for new users to seek quick assistance, while assisted bookkeeping should have been useful for trucking companies with extensive bookkeeping needs.

Nevertheless, the Tailwind interface isn’t overwhelming. The Dispatcher Dashboard is clean and uncluttered, with intuitive navigation and shortcuts that make it easy to perform common tasks like creating an order or dispatching a load.

Showing Tailwind TMS' dispatcher dashboard.Showing Tailwind TMS' dispatcher dashboard.

  1. Left navigation bar: Use this section to navigate to different areas of the software, such as quotes, orders, shipments, and equipment status.
  2. Search bar: At the top of the screen, there are two search bars that allow you to look up orders and dispatches by their number.
  3. Create a customer: You can set up a customer and add them to the database here.
  4. Create a quote: If a customer has requested a quote, you can add it here easily.
  5. Create an order: Attach all of the load details to the order in this section.
  6. Dispatch a load: This is where you can enter the information to dispatch a load.
  7. Help: Tailwind TMS support is readily available to assist you by phone, email, and in-app chat. You can also search the support center and videos for answers to your questions. On-demand training is also available.

You can contact the company by phone or email. Its Customer Success and Support Center also has articles available on virtually every topic, from settings and configuration to administration. Tailwind TMS also offers on-demand video training, both general and role-based, as well as customer support packages to set up your staff and your Tailwind TMS account.

Tailwind TMS User Reviews

4.30
/

5

Tailwind TMS is rated 4.32 out of 5 by Software Advice based on around 100 reviews. Users who left positive reviews like that the program is cloud-based, giving them the flexibility to work from anywhere. Some mentioned that it’s easy to learn and use, while others commented that it’s packed with many useful features, like the ability to track orders, drivers, and carriers. Meanwhile, those who shared negative reviews dislike that it sometimes takes a few seconds to load between pages and that integrating it with QuickBooks is laborious.

How We Evaluated the Best Trucking Accounting Software

We evaluated the best trucking accounting software based on pricing, ease of use, and the availability of general accounting features, such as A/P and A/R, and trucking-specific tools like driver and order management and equipment tracking.

10%

Pricing

25%

General Accounting Features

25%

Trucking-specific Features

30%

Ease of Use & Customer Support

10%

User Reviews

10% of Overall Score

We ranked each accounting software based on its affordability, considering the number of users included in each plan and the costs to add an extra seat.

25% of Overall Score

Regardless of the industry, specialized accounting software should include general bookkeeping features like A/P, A/R, and bank account reconciliation.

25% of Overall Score

The best trucking accounting software should be able to manage and track dispatches, orders, fuel and mileage, driver settlements, and IFTA reporting.

30% of Overall Score

We signed up for a free trial and tried the software ourselves to determine how easy it is to use. We also considered the available customer service options and how quickly the provider responds to a concern.

10% of Overall Score

We gathered unbiased user reviews from several review websites like G2 and Software Advice.

*Percentages of overall score

Frequently Asked Questions (FAQs)

Can I use Tailwind TMS for free?

While Tailwind TMS has no free version, it offers a 30-day free trial so that you can see how it works before buying.

Does Tailwind TMS integrate with QuickBooks?

Yes, it does. You can integrate all Tailwind TMS plans with QuickBooks Online and the Enterprise and Unlimited plans with QuickBooks Desktop. However, you’ll need to pay a separate subscription fee to QuickBooks.

What happens to my data if I cancel my subscription?

Envase will archive your data for three months, and during that time, you can export your data in an Excel format.

Bottom Line

Whether you’re running a small trucking company, a brokerage operation, or a combination of those two, Tailwind TMS gives you the tools to help you find and dispatch loads, invoice customers, and pay carriers, owner-operators, and drivers. It’s not as comprehensive as Q7 and QuickBooks Online, but it has enough features to help you manage your trucking business effectively.