Payroll platform Wagepoint appoints Xero North America lead Ben Richmond as president and CEO

Calgary-based payroll software Wagepoint has appointed Xero’s managing director of North America, Ben Richmond, as president and CEO.  

The New Zealand native will bring more than a decade of experience from accounting software firm Xero when he takes the reins of Wagepoint and a seat on the board of directors on August 18.

Richmond’s “deep familiarity with the Canadian landscape makes him a natural fit”

Rick Essex
PSG Equity

Richmond was responsible for driving Xero’s growth and operations across the United States and Canada, and served as in the company’s global executive leadership team, Wagepoint said in a statement. Rick Essex, the managing director of Wagepoint majority owner PSG Equity, said that Richmond’s experience serving small businesses and accounting firms “makes him an ideal leader for Wagepoint’s next stage of growth.”

“We believe his track record of expanding markets by delivering exceptional client value is well established, and his deep familiarity with the Canadian landscape makes him a natural fit,” Essex said in a statement. 

Wagepoint said that Richmond’s appointment comes at a “pivotal moment” as the company looks to roll out a modernized version of its payroll platform called “Wagepoint 2.0.” The company said this new version is built to offer faster processing, improved automation, enhanced compliance tools, and a refreshed user experience. 

Wagepoint has been talking about refreshing its product for a few years now. After it acquired Massachusetts-based Timesheet Mobile in 2022, the company said it was planning to launch a Wagepoint 2.0 that year.

In an interview with BetaKit, Wagepoint COO Neil Carew said that the initial 2.0 plans were “very ambitious” and that the company wanted to ensure it was fully ready for customers.

“Over the last year or so we’ve kind of taken a step back and said ‘let’s make sure we take the time to build this right,’” Carew said, adding that the company is currently onboarding customers to the updated product. 

Richmond succeeds Bill Hewitt, who has served as Wagepoint’s interim CEO since founding CEO Shrad Rao departed the company this past January. Hewitt will continue with the company as executive chair and remain on the board. 

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Rao announced his departure in a LinkedIn post, but at the time neither he nor the company provided any details on the circumstances. 

“I want to thank our investors at PSG for giving me the time and space to pursue other opportunities,” Rao wrote at the time. “We had a good 4-year run, and I learned a lot.” 

One week after Rao announced his departure, Wagepoint appointed Carew, then a principal with PSG, as COO. Carew told BetaKit that, as Wagepoint prepared for the 2.0 update and its “broader growth” heading into 2025, the company and Rao entered a collaborative leadership transition process. In an e-mail following the interview, Carew characterized the January leadership switch as a shift from founder-led growth to scale-oriented leadership. 

Founded in 2012, Wagepoint aims to simplify payroll with a platform that automates the processes of calculating wages and reporting on taxes. It claims to have a customer base of over 25,000 small businesses. PSG acquired a majority stake in the company in 2020, including a $10-million primary capital component to fuel acquisitions. Wagepoint used this to purchase Timesheet Mobile and KinHR. 

In 2023, Wagepoint shut down its operations in the United States. Carew said the pullback was a strategic decision to focus on its Canadian base, where it resonates best with customers, and that the company currently has no plans to return to the American market.

Feature image courtesy Wagepoint via LinkedIn.