RoadSync is digitalizing freight invoices and making payment seamless

RoadSync is digitalizing freight invoices and making payment seamless (Photo: Jim Allen/FreightWaves)

Though the freight market is roughly worth $800 billion annually to the U.S. economy, it still is reliant on old school methods of operation. This includes heavily time-consuming paper-based documentation and manual handling of recurring processes that could be automated. 

Manually done, paper-based documentation includes invoices, creating inconsistencies and reducing efficiency – a means that is contradictory to the urgency that is now associated with freight movement.

RoadSync, a digital payment platform, is showing the freight industry an easier way to record invoices and collect payment from industry stakeholders – including truck drivers, carriers and brokers. 

“We typically work with service providers like warehouses, freight handlers and heavy truck repair shops, which commonly need to collect payment from truck drivers or the back offices in real-time,” said Robin Gregg, the CEO of RoadSync. “We are almost like Square, but we’re customized for the types of payment and invoicing that happens in the transportation industry.”

Gregg comes into the startup with more than 15 years of experience in the financial services sector, having spent considerable time at FLEETCOR, serving transport-related businesses with solutions for their employees to purchase items like fuel. 

“What I’ve learned about the breadth of payments is how important efficiency and convenience is in the transportation market. What we’re trying to do is keep the drivers on the road. You don’t want them to get stuck somewhere, because they either can’t make a payment or take too long for payments to complete,” said Gregg. 

RoadSync differs from other general-purpose payment solutions by actively capturing the way people within the freight industry do their invoices. “For example, at some warehouse facilities, the management uses our platform to capture check-in and check-out time, record information on the end customer the truck driver would interact with, and register other industry-specific data like unique invoicing numbers,” said Gregg. “We are built for that as we understand how transactions happen in the industry.”

The startup currently has around 150 customers using its platform, with its services being used across at least 400 locations nationwide. Gregg explained that the feedback from customers has been very positive, with the consensus lauding RoadSync for improving the overall speed of payment processes. For RoadSync, it is about providing the freight industry a payment experience that people have come to expect as end consumers. 

“We have also improved accuracy in our clients’ ability to oversee what their employees are doing, in the case of them having multiple warehouse locations. Some customers have discovered that they charge for services inconsistently across locations – we can provide them that visibility,” said Gregg. “For the people making the payments, using our platform is convenient as it gives them a digital receipt rather than a paper copy.”

The challenge for RoadSync in the context of traction is getting in front of its potential customers to explain its services and how it can help make their financial operations more seamless. “This is not a population that has the time to Google search for different solutions. They may not be aware that we exist, so it’s about us getting in front of them,” said Gregg. 

That apart, RoadSync also confronts people who are accustomed to working a certain way and might have inhibitions to change behavior, even if it meant an improvement in efficiency. “There’s a lot of inertia. To get people comfortable, we’ve made our platform very easy to implement. We’re constantly discovering new ways for people to leverage our platform within the transportation industry,” said Gregg.

This week, RoadSync announced that it has raised $5.7 million in Series A investment, in a round led by Base10 Partners, with repeat investors Hyde Park Venture Partners and Companyon Ventures. The startup intends to utilize the funding towards expanding its development team and its sales capacity. RoadSync will also be investing in the platform by improving workflow automation and adding new financial services as prioritized by its customer base. 

Upcoming FreightWaves Events
Compliance

Brokerage Compliance Symposium

The day before F3. Every compliance issue you face - fraud exposure, carrier liability, FMCSA rules, cargo theft, insurance gaps - navigated by attorneys and operators defining best practices in a changing industry.

October 26, 2026
The Signal at Chattanooga Choo Choo • Chattanooga, TN
Register Now
Awards

F3 Awards Dinner

The night before F3. FreightTech100 companies honored. FreightTech 25 and Shipper of Choice winners revealed live. Cocktail reception into dinner and live music - 300 industry leaders in one purpose-built room.

October 26, 2026
The Signal at Chattanooga Choo Choo • Chattanooga, TN
Register Now
FreightTech

F3: Future of Freight Festival

Industry-defining keynotes, rapid-fire technology demos, and industry leaders networking in experiences across Chattanooga - plus the inaugural F3 Awards Dinner featuring the FreightTech and Shipper of Choice reveals.

October 27, 2026 – October 28, 2026
The Signal at Chattanooga Choo Choo • Chattanooga, TN
Register Now
Compliance Brokerage Compliance Symposium Oct 26 • The Signal at Chattanooga Choo Choo • Chattanooga, TN

The day before F3. Every compliance issue you face - fraud exposure, carrier liability, FMCSA rules, cargo theft, insurance gaps - navigated by attorneys and operators defining best practices in a changing industry.

The Signal at Chattanooga Choo Choo • Chattanooga, TN Register Now
Awards F3 Awards Dinner Oct 26 • The Signal at Chattanooga Choo Choo • Chattanooga, TN

The night before F3. FreightTech100 companies honored. FreightTech 25 and Shipper of Choice winners revealed live. Cocktail reception into dinner and live music - 300 industry leaders in one purpose-built room.

The Signal at Chattanooga Choo Choo • Chattanooga, TN Register Now
FreightTech F3: Future of Freight Festival Oct 27 – Oct 28 • The Signal at Chattanooga Choo Choo • Chattanooga, TN

Industry-defining keynotes, rapid-fire technology demos, and industry leaders networking in experiences across Chattanooga - plus the inaugural F3 Awards Dinner featuring the FreightTech and Shipper of Choice reveals.

The Signal at Chattanooga Choo Choo • Chattanooga, TN Register Now