Contractor management platform PayShepherd closes $7 million CAD as product, market expansion continues

Inovia Capital-led round aimed at cementing firm’s presence in the United States and Canada.

Calgary-based billing software startup PayShepherd has secured $7 million CAD in its second seed financing aimed at expanding the company’s presence in its target markets across North America, namely in the forestry, mining, manufacturing, and energy sectors.

The startup also looks to bolster its platform with artificial intelligence this year, which will allow some clients to automate components of their administrative processes. 

The all-equity funding round, which closed in early February, was led by Inovia Capital and saw participation from existing investors Nashville Capital Network, Thin Air Labs, Accelerate Fund III (which is managed by Yaletown Partners with support from A100), as well as undisclosed strategic angel investors. 

Inovia partner Shawn Abbott will join PayShepherd’s board as part of the fundraise, the company said in a statement. 

PayShepherd’s software helps heavy industrial and manufacturing facilities manage contractor billing and eliminate overspending by centralizing contractor billing submissions. The platform then automatically verifies the data against factors such as contract terms, expected gate entries, and work orders. 

RELATED: PayShepherd closes $3.8 million CAD to fuel North American expansion of contractor billing solution

Founded under the name Project Recapture in 2018 by CEO Wesley Sessenwin, director of operations Jennifer Hunter, and director of technology John Lee, PayShepherd says its customers include multinational conglomerates with dozens of facilities in their portfolio, spanning pulp and paper, chemicals, manufacturing, and other verticals.

The recent seed round comes almost two years after PayShepherd raised $3 million USD ($3.8 million CAD) in seed funding, which it used to grow its team and presence across verticals like mining and energy. PayShepherd says it has raised $12.1 million CAD in equity financing to date. 

“Wes and team have done a beautiful job of delivering transparency, accountability, and lightning speed to the frustrating and stubbornly manual workflows in coordinating large contracted workforces at the heavy industry sites that are the backbone of our economy’’ Abbott said in a statement. 

PayShepherd says it has managed billions in contractor cost submissions since its launch and intends to further expand into Canada and the United States, as well as Europe, where PayShepherd told BetaKit it is experiencing “incredible demand.” 

“[Europe is] dealing with a unique set of geo-political challenges that have compounded the margin pressure,” PayShepherd said to BetaKit in an email statement. “The market sees PayShepherd as a solution to this pressure.”

Feature image by gpointstudio via Freepik.

Alex Riehl

Alex Riehl

Alex Riehl is a staff writer and newsletter curator at BetaKit with a Bachelor of Journalism from Carleton University. He's interested in tech, gaming, and sports. You can find out more about him at or @RiehlAlex99 on Twitter.

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