Freight billing gets AI boost as Kleinschmidt backs Upwell

AI-powered invoice auditing

At the center of the partnership is Upwell’s audited billing platform, which reviews freight invoices against shipper-specific billing requirements before they are submitted for payment.

The audit engine verifies items such as proof-of-delivery documentation, reference numbers, lumper receipts, accessorial charges, shipment weights, contract rates and fuel surcharge calculations. Invoices that satisfy all requirements are submitted automatically, while exceptions are routed for human review.

Charley Dehoney, CEO and co-founder of Upwell, said payment delays are often caused by invoice discrepancies rather than a lack of willingness to pay.

“The biggest delays in freight payments aren’t just about timing; they’re about trust and accuracy,” Dehoney said in a statement. “Kleinschmidt’s network is where freight’s most trusted data lives. By partnering with them, we can meet carriers where their data already is, validate it upfront, and help them get paid quickly without the usual back-and-forth.”

Carriers report faster payments

The companies highlighted early success from carriers already using both platforms.

Curt Morehouse, co-owner of Morehouse Trucking, said the integration has automated several manual billing processes while improving payment speed from major customers.

“Upwell has been a game-changer for our business,” Morehouse said. “We’ve automated manual work steps and shown a significant increase in payment speed from some of our largest shippers.”

Giltner Logistics also reported lower days sales outstanding and improved visibility into accounts receivable through the platform, according to the release.

Focus on cash flow during freight downturn

The announcement underscores a growing trend in transportation technology: applying artificial intelligence and automation to back-office functions traditionally handled through manual processes.

“Manual back-office processes were once viewed as a necessary expense,” Dehoney said. “Today, operators that automate them are gaining a meaningful advantage with stronger cash flow, more focused teams, and the capacity to grow with confidence.”

For carriers already connected to Kleinschmidt’s network, Heinen said the partnership expands what can be done with existing freight data connections.

“For carriers already on the Kleinschmidt network, nothing changes today except what’s possible,” Heinen said. “The connection you trust now powers something bigger: end-to-end AR automation.”

Founded more than 40 years ago and headquartered in Deerfield, Illinois, Kleinschmidt provides B2B integration and EDI services for carriers, brokers, shippers and third-party logistics providers. 

Omaha, Nebraska-based Upwell specializes in freight billing automation, accounts receivable management and payment acceleration solutions for the transportation industry.