Two Different Starting Points
Tailwind TMS has been in the market for years and was acquired by WiseTech Global (CargoWise) in 2023. It handles both carrier-side and broker-side operations, which makes it a natural fit for hybrid businesses that broker some loads and haul others. HaulerPro is a different kind of tool: a cloud-native TMS designed from the ground up for independent carriers and small fleets, owner-operators through 15 or more trucks, running reefer, dry van, flatbed, hotshot, box truck, or LTL freight.
Neither product is right for every operation. This page goes through each major feature area honestly so you can figure out which one fits your business.
Dispatch
HaulerPro dispatch lives on a single screen. A manager or dispatcher builds a load, assigns it to a driver, and the driver gets a text notification when the load lands in their app. Drivers update load status by hand from the driver app, and those updates flow to dispatch and show on the load record. No GPS, no live map. Just a clean status trail that tells dispatch where things stand.
Tailwind's dispatch workflow handles both carrier and broker operations, including customer quoting, order management, and electronic rate confirmation and acceptance, per their marketing site. That breadth is genuinely useful if you broker freight and haul freight from the same office. If you only haul, that extra surface area may be more than you need.
Documents
With HaulerPro, a driver opens the app, picks the load, and scans the document right there. Rate confirmations, BOLs, and PODs attach to that specific load record. When you generate an invoice, the POD auto-attaches. Rate confirmations and other delivery documents do not auto-attach to the invoice, but they are on the load record where you can pull them at any time.
Tailwind offers a companion mobile app called POD Complete for iOS and Android, focused on BOL and POD capture, per their marketing site. They also support emailing documents directly from the TMS and business document customization. Customer and carrier portals are available on their Enterprise and Unlimited tiers.
Both products get documents off paper and into a load record. The difference is scope: Tailwind's document tools are part of a broader brokerage-and-carrier platform, while HaulerPro's are built around the carrier workflow specifically.
Invoicing
HaulerPro generates an invoice in one click from a completed load. The POD auto-attaches. From inside HaulerPro, you can submit the invoice to a factoring partner, which gets the paperwork moving without having to switch tabs or re-enter data. A separate factoring relationship is required; HaulerPro handles the submission step.
Tailwind's invoicing is part of a full accounts receivable and accounts payable module, per their marketing site. That includes driver and carrier settlements, a sales commission system, and the ability to print checks from the TMS. It also syncs with QuickBooks Online on their Plus tier or higher. If you want a TMS that replaces your accounting software, Tailwind's built-in A/R and A/P is a real advantage. If you just need clean invoices out the door fast, HaulerPro's one-click approach keeps it simple.
Drivers and Settlements
HaulerPro keeps each driver's CDL and medical card on file, with expiration dates, photos, and reminders at 60, 30, and 7 days out, plus on the expiration date. Driver settlements are generated from the loads and time entries already in the system. Five pay bases are available: percentage of load, flat per load, per mile, per day, and per hour. You can add labeled deductions per settlement (fuel advance, escrow, insurance, and similar), and the statement shows gross pay, total deductions, and net pay. Double-pay protection means a load already settled cannot be pulled onto a later statement by accident. Each driver sees their own statements in a read-only view inside the driver app.
Tailwind includes driver and carrier settlements, per their marketing site. Specific mechanics of how settlements are configured and what pay structures are supported are not detailed on their public marketing pages.
IFTA Reporting
HaulerPro captures per-jurisdiction miles automatically from each dispatched load using route-based polygon intersection across the 48 contiguous states. Fuel receipts are scanned by the driver and stored on the load record, but fuel is not auto-attributed to a jurisdiction. At the end of the quarter, the mileage panel aggregates miles by state and you export an ifta_miles.csv. HaulerPro works out miles by state from each load's route for the 48 contiguous states, and the carrier or their accountant files the quarterly return. HaulerPro does not prepare or submit the return, and there is no error-flagging or inconsistency detection built in. If you want to avoid common mistakes before you hand the data to your accountant, see our guide on common IFTA mistakes.
Tailwind lists IFTA as a named feature on their marketing site. The specific mechanics of how miles are captured and how fuel data flows are not publicly documented in detail, so a direct apples-to-apples comparison is not possible here. If IFTA reporting is a priority decision-point for you, ask Tailwind's team specifically how their mileage capture works and whether it covers all the states you run.
Fleet and Maintenance
HaulerPro has an optional fleet inventory for trucks and trailers. Each vehicle can carry a full service history: service type, date, odometer reading, cost, and vendor. The system computes a next-due date from a service interval in months and next-due miles from an interval in miles when you enter an odometer reading. In-app reminders flag vehicles that are due soon or overdue, and there is a fleet-wide list of everything that needs attention. Reminders show inside the app only; no email or push notifications go out for maintenance. A built-in service library suggests common service types and default intervals as guidance, not as a compliance guarantee.
Tailwind's maintenance and fleet management capabilities are not publicly detailed on their current marketing pages, so no comparison is possible on this dimension.
Integrations
Tailwind's integration list is one of its genuine strengths for carriers who need connections outside the TMS. Per their marketing site, Tailwind connects with QuickBooks Online (Plus tier or higher), DAT, Truckstop, 123Loadboard, NextLoad, Google Maps, Here for mileage and mapping, BorderConnect for ACE and ACI cross-border manifests, RMIS for carrier onboarding, multiple fuel card networks (Comdata, EFS, Pilot Flying J, Multi Service, QUIKQ, BVD Petroleum, Fleet One, Husky), and Kleinschmidt EDI. That is a substantial integration footprint, especially the fuel card connections and cross-border manifest support.
HaulerPro's integration list is shorter and focused on the workflows independent carriers use most. Inside HaulerPro, you can search loads through a 123Loadboard integration and a FreightLink integration; both are display-only searches and each requires a separate subscription to that service. You can also submit invoices to a factoring partner directly from HaulerPro. HaulerPro does not currently integrate with QuickBooks, ELD hardware, or EDI systems. If those connections are non-negotiable for your operation, Tailwind has a clear edge on integrations.
Pricing
HaulerPro pricing is per user, not per truck. Every login counts: managers, dispatchers, and drivers all count as users. The plan structure is:
- Basic: $59/month for 1 to 2 users, plus $29/month for each added user
- Starter: $95/month for up to 5 users ($124/month for 6 users, $182/month for 8 users, $240/month for 10 users)
- Growth: $250/month for 11 to 15 users
- Over 15 users: contact sales
Annual billing is 10 times the monthly rate, which works out to two months free compared to paying month to month. There is a 14-day free trial with no credit card required.
Tailwind does not publish pricing on their marketing site as of the time this was written. Third-party aggregators have reported figures in the range of $99 to $265 per user per month depending on tier, but those figures come from aggregator listings, not from a Tailwind-controlled or CargoWise-controlled page, and they may be stale following the WiseTech Global acquisition. Contact Tailwind's sales team directly for current pricing before you budget for it.
Support
HaulerPro offers founder-led support from someone who built the software around how carriers actually work.
Tailwind lists email and phone support, with contact information (support@tailwindtms.com and 1-866-441-0441) appearing in vendor responses to public reviews on software review sites. Specific support hours and service level details are not publicly documented on their current marketing pages.
When Each One Fits Better
HaulerPro is likely the better fit if you:
- Run an independent carrier operation, owner-operator through about 15 users, and want a tool built specifically for that world
- Need clean dispatch, invoicing, driver settlements, IFTA mileage capture, and document scanning without a lot of extra surface area for brokerage functions you do not use
- Want predictable, transparent per-user pricing with a free trial and no credit card up front
- Want maintenance tracking and driver document expiration reminders built into the same platform
Tailwind is likely the better fit if you:
- Run a hybrid operation that brokers freight and hauls freight, and need both sides in one platform
- Need deep integration with fuel card networks, EDI, or cross-border manifest systems
- Want built-in accounts receivable and accounts payable tools that can replace a separate accounting package
- Already use QuickBooks Online and want your TMS to sync with it natively
Both products are cloud-based and serve small to mid-sized operations. The real question is whether you need a platform built for brokers and carriers together, or one built for carriers specifically. If it is the latter, HaulerPro is worth a serious look.
Compare other options on our TMS comparison index or read about the features HaulerPro brings to independent carriers at haulerpro.app.
Ready to see how it runs for your operation? Start a free trial and have loads moving before your next run. No credit card required, no implementation consultant, no contract. Start your 14-day free trial and see if HaulerPro fits the way you work.