How Endless TMS compares to Tailwind Transportation Software on dispatch, tracking, invoicing, pricing, and integrations for Small-to-mid freight brokerages and asset carriers in North America.
Tailwind Transportation Software is a cloud-based TMS founded in 2007 and headquartered in Waterloo, Ontario, Canada. It targets freight brokerages and asset carriers operating in North America, with particular strength in cross-border US/Canada operations. The platform covers the full broker lifecycle — carrier sourcing, rate quoting, load tendering, document management, and invoicing — alongside carrier-side dispatch and driver management. Tailwind offers EDI connectivity, which is important for shippers and partners that exchange load tenders electronically. Its pricing model is per-user, meaning costs scale with team size rather than fleet size. The product has accumulated a loyal customer base in the small-to-mid brokerage segment over its 15+ year history. The interface reflects the era in which the product was built and has been incrementally updated rather than redesigned, which some users find functional but dated. Tailwind integrates with QuickBooks and several load boards. It is a credible choice for established brokerages that prioritize breadth of features and EDI support over modern UX or mobile-first workflows.
| Feature | Endless TMS | Tailwind Transportation Software |
|---|---|---|
| Dispatch | ||
Load dispatch | ||
Broker load workflow | ||
Multi-stop trip planning | ||
| Tracking | ||
Real-time GPS tracking Tailwind does not include built-in continuous GPS; relies on manual updates or ELD integrations | ||
ELD integration | ||
Auto-stop tracking on delivery | ||
| Invoicing | ||
Customer invoicing | ||
QuickBooks integration | ||
EDI support | ||
Fuel surcharge automation | ||
| Driver Tools | ||
Driver mobile app Tailwind has limited driver-facing mobile features | ||
Driver document upload (POD) | ||
Driver settlements / pay statements | ||
| Integrations | ||
Load board integration (DAT / Truckstop) | ||
API access | ||
Multi-tenant / white-label | ||
| Pricing & Billing | ||
Per-user pricing available | ||
Per-truck pricing available | ||
| Support | ||
Live chat / email support | ||
Dedicated onboarding | ||
Pricing model: per user.
Tailwind supports both brokers and asset carriers. Its broker workflow — including carrier sourcing, rate management, and load tendering — is one of its strengths, and many customers use it for hybrid brokerage-plus-asset operations.
Tailwind does not include built-in continuous GPS tracking. Load location visibility relies on manual dispatcher or driver updates, or on a connected ELD device. Fleets that need real-time location data typically integrate a separate tracking solution.
Yes. Tailwind includes EDI support for exchanging load tenders and status updates with shippers and partners electronically. This is one of Tailwind's differentiated capabilities compared to newer, lighter-weight TMS products.
Per-user pricing means your cost scales with the number of dispatcher and admin seats, regardless of fleet size. For asset carriers, this can be more or less expensive than per-truck pricing depending on the ratio of trucks to staff. Brokerages with small teams often find per-user pricing favorable.
Yes, Tailwind is headquartered in Waterloo, Ontario, Canada, and has historically served a significant Canadian customer base. It supports cross-border US/Canada operations including Canadian dollar billing and relevant compliance fields.
Competitor information verified on 2026-05-26.