Freddy Kassulke-Boyle's review of TruckMate

Emory RolfsonJan 2026

…and the billing finally stopped being the bottleneck. We used to wrestle with spreadsheets and an old TMS that spat out invoices you had to re-enter by hand; TruckMate automated that whole flow and cut our invoice-to-pay time from 30–45 days down to around 10–15, which actually eased cash flow pressure. After 16 years running 85 trucks in the Pacific Northwest, that single change made a bigger operational difference than any routing tweak ever did. The dispatch board took a little getting used to and a few screens feel cluttered, but the faster settlements more than made up for the small headaches.

Larissa LemkeJan 2026

I've been running a 50-truck fleet in the Northeast for 18 years, and we brought TruckMate on nine months ago to replace a patchwork of spreadsheets. When their invoicing module started undercharging intermodal accessorials, support took days to acknowledge the bug and then closed tickets without fixing the root cause - leaving us to manually correct dozens of invoices. That delay cost us roughly $8k in one billing cycle and tied up two office staff for nearly a week; a few shippers even threatened to pull loads because payment windows were missed. Live chat seemed scripted and the assigned account rep stopped answering once the problem required engineering attention, so escalation felt impossible. The software has potential, but their customer service failures make billing errors a real cash-flow risk for a fleet this size.

Jordon LittelJan 2026

Bottom line: TruckMate's automated invoicing actually cut my admin time a lot, but its settlement/payment matching is unreliable enough that I still have to babysit every billing run. I run three trucks on the West Coast and the auto-fill for accessorials and fuel surcharge usually nails it, yet a couple times a month it misapplies payments or spits out duplicate adjustments - spent an hour last week untangling a single week's batch.