---
description: Quickly find and compare the leading Tailwind TMS vs TruckingOffice alternatives. Comprehensive listing of competitors & similar tools for fast software selection and to contact several providers directly.
image: https://gdm-localsites-assets-gfprod.imgix.net/images/getapp/og_logo-94fd2a03a6c7a0e54fc0c9e21a1c0ce9.png
title: Compare Tailwind TMS vs TruckingOffice | GetApp Canada 2026
---

Breadcrumb: [Home](/) > [Fleet Management Software](/directory/217/fleet-management/software) > [Tailwind TMS \<span\>vs\</span\> TruckingOffice](https://www.getapp.ca/compare/103137/106679/tailwind/vs/truckingoffice)

# Compare Tailwind TMS vs TruckingOffice

Canonical: https://www.getapp.ca/compare/103137/106679/tailwind/vs/truckingoffice

> Detailed comparison between Tailwind TMS and TruckingOffice. Check ratings, reviews, pricing, and features to make the best decision for your business.

-----

## At a Glance

| Metric | Tailwind TMS | TruckingOffice |
| **Overall rating** | 4.2/5 | 4.4/5 |
| **Total Reviews** | 97 | 38 |
| **Starting Price** | US$99.00 | US$20.00 |
| **Free Trial** | Yes | Yes |
| **Free Version** | No | No |
| **Deployment** | Cloud, SaaS, Web-based, Mac (Desktop), Windows (Desktop), Linux (Desktop), Chromebook (Desktop), Android (Mobile), iPhone (Mobile), iPad (Mobile) | Cloud, SaaS, Web-based |
| **Support** | Email/Help Desk, FAQs/Forum, Knowledge Base Software, Phone Support, 24/7 (Live rep), Chat | Email/Help Desk, Phone Support, Chat |
| **Training Software** | In Person, Live Online, Webinars, Documentation, Videos | Live Online, Videos |

## Key features

### Tailwind TMS

- Billing & Invoicing
- Carrier Management
- Contact Database
- Dispatch Management
- Driver Management
- EDI Software
- GPS
- LTL/Shared Truckload
- Live Driver Tracking
- Load Optimization
- Maintenance Management Software
- Maintenance Scheduling
- Mileage Tracking
- Order Management Software
- Routing
- Scheduling Software
- Shipment Tracking Software
- Transportation Management Software
- Truckload Management
- Vehicle Management

### TruckingOffice

- Billing & Invoicing
- Carrier Management
- Contact Database
- Dispatch Management
- Driver Management
- EDI Software
- GPS
- LTL/Shared Truckload
- Live Driver Tracking
- Load Optimization
- Maintenance Management Software
- Maintenance Scheduling
- Mileage Tracking
- Order Management Software
- Routing
- Scheduling Software
- Shipment Tracking Software
- Transportation Management Software
- Truckload Management
- Vehicle Management

## Links

- [View Tailwind TMS Profile](https://www.getapp.ca/software/103137/tailwind)
- [View TruckingOffice Profile](https://www.getapp.ca/software/106679/truckingoffice)
- [View Original Comparison](https://www.getapp.ca/compare/103137/106679/tailwind/vs/truckingoffice)

-----

## Structured Data

<script type="application/ld+json">
  {"@context":"https://schema.org","@graph":[{"name":"Compare Tailwind TMS vs TruckingOffice | GetApp Canada 2026","description":"Quickly find and compare the leading Tailwind TMS vs TruckingOffice alternatives. Comprehensive listing of competitors & similar tools for fast software selection and to contact several providers directly.","url":"https://www.getapp.ca/compare/103137/106679/tailwind/vs/truckingoffice","about":[{"@id":"https://www.getapp.ca/software/103137/tailwind#software"},{"@id":"https://www.getapp.ca/software/106679/truckingoffice#software"}],"breadcrumb":{"@id":"https://www.getapp.ca/compare/103137/106679/tailwind/vs/truckingoffice#breadcrumblist"},"@id":"https://www.getapp.ca/compare/103137/106679/tailwind/vs/truckingoffice#webpage","@type":["WebPage","CollectionPage"],"publisher":{"@id":"https://www.getapp.ca/#organization"},"inLanguage":"en-CA","isPartOf":{"@id":"https://www.getapp.ca/#website"}},{"name":"Tailwind TMS","description":"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. \n\nTailwind 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.\n\nTailwind 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. \n\nTailwind 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.\n\nTailwind 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.","image":"https://gdm-catalog-fmapi-prod.imgix.net/ProductScreenshot/53897229-1d20-47df-a18c-0fdac968eb29.png","url":"https://www.getapp.ca/software/103137/tailwind","@id":"https://www.getapp.ca/software/103137/tailwind#software","@type":"SoftwareApplication","applicationCategory":"BusinessApplication","publisher":{"@id":"https://www.getapp.ca/#organization"},"aggregateRating":{"@type":"AggregateRating","ratingValue":4.2,"bestRating":5,"ratingCount":97},"offers":{"price":"99","@type":"Offer","priceCurrency":"USD"},"operatingSystem":"Cloud, Apple, Windows, Linux, Chrome, Android, Platform ios, Platform ipad"},{"name":"TruckingOffice","description":"TruckingOffice is an online trucking management software for small and mid-sized trucking businesses with up to 10 delivery trucks. The solution offers various trucking management features such as load planning, dispatch management, driver settlement, expense monitoring, tax filing, and reporting.\n\nTruckingOffice helps truck owners to file Interstate Fuel Tax Agreements (IFTA) and ensures that all business records are compliant with standard reporting and auditing norms. The software’s dispatch management module helps to record drivers’ and customers’ personal details. The tool lets business managers enter driver's pay details and automate their monthly payment based on the deliveries made. The built-in invoicing tool allows users to create invoices and send digital copies to customers directly via email. The solution offers interactive customization tools to create personalized agreements and invoices that can be exported in multiple file formats or be shared with customers electronically.\n\nTruckingOffice supports multiple driver payment models including pay per mile, pay by percentage, manual pay entry, and fixed monthly pay. The solution also offers different payment structures for permanent and temporary drivers. The software’s real-time alert and notification features enable business owners to set alerts for key milestones such as registrations renewal, agreement expiry, driver's CDL, medical cards expiry, and preventive maintenance.\n\nTruckingOffice collaborates with PC Miler to calculate miles and integrates with QuickBooks to handle accounting needs. The solution offers customer support via email, phone, and video tutorials.","image":"https://gdm-catalog-fmapi-prod.imgix.net/ProductScreenshot/b308400c-19a9-4149-bcc6-25c03581f513.png","url":"https://www.getapp.ca/software/106679/truckingoffice","@id":"https://www.getapp.ca/software/106679/truckingoffice#software","@type":"SoftwareApplication","applicationCategory":"BusinessApplication","publisher":{"@id":"https://www.getapp.ca/#organization"},"aggregateRating":{"@type":"AggregateRating","ratingValue":4.4,"bestRating":5,"ratingCount":38},"offers":{"price":"20","@type":"Offer","priceCurrency":"USD"},"operatingSystem":"Cloud"},{"@id":"https://www.getapp.ca/compare/103137/106679/tailwind/vs/truckingoffice#breadcrumblist","@type":"BreadcrumbList","itemListElement":[{"name":"Home","position":1,"item":"/","@type":"ListItem"},{"name":"Fleet Management Software","position":2,"item":"/directory/217/fleet-management/software","@type":"ListItem"},{"name":"Tailwind TMS vs TruckingOffice","position":3,"item":"https://www.getapp.ca/compare/103137/106679/tailwind/vs/truckingoffice","@type":"ListItem"}]}]}
</script>