If you've searched "Tailwinds TMS" or "Tailwind TMS," you've likely landed on the platform now operated by WiseTech Global under the CargoWise brand. It's a real product with a real feature set, and it's worth understanding what it covers, who it's built for, and where a platform like HaulerPro fits differently for independent carriers and small fleets.
This article gives you the facts on Tailwind TMS, then shows you what HaulerPro does for the owner-operator and small-fleet side of the market that enterprise-leaning tools tend to overlook.
What Is Tailwind TMS?
Tailwind TMS is a cloud-based transportation management system designed for motor carriers, freight brokerages, and companies that operate as both. WiseTech Global (CargoWise) acquired Tailwind in 2023. The platform targets small and mid-sized operations, but its feature set and integration depth reflect a product built for companies managing significant operational complexity, including broker workflows alongside carrier dispatch.
Three pricing tiers are offered: Pro, Enterprise, and Unlimited. Tailwind's official CargoWise marketing page does not list specific prices. Third-party aggregators have reported figures in the range of roughly $99 to $265 per user per month across tiers, but those figures may be stale or inconsistent post-acquisition. Verify current pricing directly with Tailwind before making any budget decisions.
What Tailwind TMS Covers
Based on verified public sources, Tailwind includes the following capabilities:
- Dispatch and shipment status: Status-based dispatch with trip logs. Driver-entered status updates are the native model.
- Quoting and order management: Customer quotes, electronic load and rate confirmation, order management.
- Integrated accounting: Accounts receivable, accounts payable, general ledger, driver and carrier settlements, QuickBooks Online sync (higher tiers required).
- Documents: The POD Complete mobile app (iOS and Android) handles BOL and POD capture. Documents can be emailed directly from the TMS.
- Compliance: Equipment maintenance records, claims and incident logging, SaferWatch FMCSA data feed.
- Customer and carrier portals: Available on Enterprise and Unlimited tiers.
- IFTA: Mileage calculations and fuel bill importing are listed as features. Third-party reviews describe IFTA workflow used in production, supported by routing integrations including Here and Google Maps, plus fuel card integrations (Comdata, EFS, Pilot Flying J, and others).
- Reporting: Management, accounting, and operations reports. Power BI integration on the Unlimited tier.
- API and integrations: Named partners include Samsara, DAT, Truckstop, 123Loadboard, Trucker Tools, Descartes MacroPoint, EZTrack, Google Maps, Here, BorderConnect (ACE/ACI), RMIS, Kleinschmidt EDI, and multiple fuel card providers.
Tailwind's integration list is broad. If your operation relies on specific ELD hardware or fuel card programs, it's worth checking whether your provider is on their verified partner list before committing.
Who Tailwind TMS Is Built For
Tailwind's public positioning covers small and mid-sized trucking companies and freight brokerages equally. That dual-audience design means a meaningful portion of the feature set, including carrier portals, customer portals, and brokerage-side quoting, serves hybrid broker-carrier operations rather than carriers running their own trucks exclusively.
If you're an independent carrier or a small fleet without a brokerage arm, you're paying for architecture designed around a broader use case. That's not a flaw in the product. It's just a fit question worth asking before you sign up.
Where HaulerPro Fits Instead
HaulerPro is built for independent carriers and small fleets: reefer, dry van, flatbed, hotshot, box truck, LTL, from owner-operators up to about 15 trucks. There's no brokerage layer, no implementation consultant, and no onboarding fee. You can have your first load live in under 10 minutes from signup.
Here's what HaulerPro covers in one platform:
- Dispatch: One-screen dispatch. Once you're set up, dispatching a load to a driver takes under 60 seconds.
- Documents: Drivers scan BOLs, rate confirmations, and fuel receipts from their phone, attached directly to the load. PODs auto-attach to the invoice for that load.
- Invoicing: One-click invoice generation from a completed load. POD is already attached.
- IFTA: Per-jurisdiction miles are auto-captured from dispatched loads via OSRM routing across the 48 contiguous states and DC. Fuel receipts are scanned and stored on the load. The quarterly panel aggregates your miles and exports an
ifta_miles.csv. HaulerPro captures the mileage; verifying the numbers and submitting them to your base jurisdiction stays with you. - Expenses: Log expenses per load or per truck. See real profit on every run, not just top-line revenue.
- Driver settlements: Generate settlement statements from dispatched loads and time entries. Supports percentage of load, flat per load, per mile, per day, and per hour pay bases. Per-settlement deductions (fuel advance, escrow, insurance, chargeback) are supported. Each statement is an immutable snapshot. Drivers see their own settlements in a read-only view in the app.
- Fleet and maintenance: Optional fleet inventory for trucks and trailers. Per-vehicle service history with due-soon and overdue reminders shown in-app.
- Driver notifications: When a load is assigned, the driver gets a text message. Consent-based, with STOP opt-out.
- Load search: HaulerPro integrates with 123Loadboard so you can search loads from inside the platform. A separate 123Loadboard subscription is required.
- Support: Founder-led support from someone who built the software around how carriers actually work.
Pricing starts at $95 per month for up to 5 users (managers, dispatchers, and drivers all count as users). Up to 15 users is $250 per month. The 14-day free trial requires no credit card.
Tailwind TMS vs. HaulerPro: A Quick Side-by-Side
- Target audience: Tailwind serves carriers and freight brokerages. HaulerPro is focused on independent carriers and small fleets.
- Pricing transparency: Tailwind does not publish pricing on their official site. HaulerPro publishes pricing at $95/mo and $250/mo.
- IFTA: Tailwind has IFTA workflow supported by fuel card integrations and routing data. HaulerPro auto-captures per-jurisdiction miles and exports a quarterly mileage file; fuel receipts are scanned and stored on the load.
- Driver status updates: Both platforms use driver-entered status updates as the native model. Status updates flow from the driver app to dispatch on both platforms.
- Setup time: HaulerPro is designed for self-serve setup with first load live in under 10 minutes. Tailwind's implementation path for small carriers is not publicly detailed.
- Accounting: Tailwind has full integrated A/R and A/P with QuickBooks Online sync. HaulerPro handles invoicing and driver settlements but does not integrate with QuickBooks.
- Free trial: HaulerPro offers a 14-day free trial, no credit card required. Tailwind's trial availability is not confirmed on their current public marketing page.
For more context on how to evaluate TMS options as an independent carrier, see the HaulerPro guides index.
Bottom Line
Tailwind TMS is a capable platform with a broad integration network and accounting depth that suits carrier-broker hybrid operations and mid-sized fleets with complex workflows. If that's your operation, it's worth a conversation with their team.
If you're an independent carrier or a small fleet who needs dispatch, documents, invoicing, per-jurisdiction IFTA mileage, driver settlements, and expenses in one place without the enterprise overhead, HaulerPro was built for that. No brokerage features you'll never use. No implementation timeline. No credit card to start.
Start your 14-day free trial and have your first load live in under 10 minutes. No credit card required.