Innovators of the Week: PayShepherd Helps Industrial Sites and Contracted Workforces Get Organized

The contractor management platform recently closed a $7 million CAD funding round, with plans to expand throughout North America.

L-R: Wesley Sessenwein, Jenn Hunter and Johan Lee. Photo courtesy of PayShepherd.

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Wesley Sessenwein had worked with many industrial clients over countless years before starting PayShepherd in 2018 with co-founders Jenn Hunter and Johan Lee.

PayShepherd is a contractor management software that centralizes, digitizes and verifies data on labour, equipment and materials to alert business owners of risks and opportunities across their operations.

As Sessenwein recalls, many of the headaches during his time working with or as a contractor stemmed from the potential for mismanagement of multiple figures, usually due to endless administrative tasks and paperwork. In other words, disorganization. Those types of situations were the catalyst for PayShepherd, a contractor management solution to streamline data.

“When business is good, the paperwork volume is high, and there’s a lot of opportunity to either make or break your business,” says Sessenwein.

In March, the company closed a $7 million CAD Seed+ round and said that this funding will support PayShepherd’s continued expansion throughout North America, plus add new capabilities to its platform such as more automation, working in large language models and incorporating artificial intelligence. New investor Inovia Capital led the round, with participation from PayShepherd’s existing investors Nashville Capital Network, Thin Air Labs, Accelerate Fund III (managed by Yaletown Partners with support from The A100), as well as additional, undisclosed, strategic angel investors. With that round of funding, PayShepherd has now raised $12 million CAD in total to date.

“I think as an entrepreneur, you have the ability to go in search of a problem to solve or get punched in the face with a problem that you need to solve,” says Sessenwein. “And for us, it was the second one. We had lived this pain over and over and wondered how there wasn’t a solution already.”

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