Calgary-based payroll software company Wagepoint has appointed Ben Richmond as president and chief executive officer, effective August 18, 2025. Richmond will also join the company’s board of directors.
Richmond brings over 15 years of leadership experience in financial technology and software-as-a-service companies, with a focus on serving small and medium-sized businesses. He most recently served as managing director for North America at Xero, where he was responsible for growth and operations across U.S. and Canadian markets and served on the company’s global executive leadership team.
The appointment comes as Wagepoint rolls out version 2.0 of its payroll platform, which the company says offers faster processing, improved automation, enhanced compliance tools and an updated user experience designed for small businesses and their advisors.
Richmond’s background and experience
Originally from New Zealand, Richmond joined Xero in 2013 and held various roles in sales, growth and market expansion across New Zealand and the Americas. He began his career in public accounting and served as senior group accountant at Spark New Zealand. Richmond also served as a trustee for the Spark Foundation, a charitable organization supporting digital equity in New Zealand.
Richmond is a chartered accountant and holds a bachelor of commerce degree in accounting, finance and information systems from the University of Canterbury. His work in accounting technology and transformation earned him recognition as one of Accounting Today’s Top 100 Most Influential People in 2019 and 2020, a CPA Practice Advisor 20 Under 40 honoree in 2020, and the Chartered Accountants Australia and New Zealand Institute of Chartered Accountants Westpac Outstanding New Member of the Year award in 2013.
Leadership transition and company backing
Richmond succeeds Bill Hewitt, who has served as interim CEO since early 2025. Hewitt will continue as executive chair and remain on the board of directors.
“Ben’s experience serving small businesses and accounting firms makes him an ideal leader for Wagepoint’s next stage of growth,” said Rick Essex, managing director at PSG Equity. “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. We’re thrilled to welcome him to the team.”
Richmond said he is honored to join Wagepoint at this time. “Small businesses are the backbone of the economy, and Wagepoint has built a strong foundation with its simple, human-focused payroll solutions,” he said. “With my experience across SMBs, payments, and go-to-market strategy, I’m excited to help lead the next stage of growth as we scale the digitization of Canadian small business. I look forward to working with our teams, accountants, and bookkeepers to deliver even greater value and delight to our customers.”
About Wagepoint
Founded in 2012, Wagepoint serves over 25,000 small businesses, accountants and bookkeepers across Canada. The company’s software automates wage calculations and tax filings for small businesses. PSG Equity, a growth equity firm that partners with software and technology-enabled services companies, backs Wagepoint.
