Leading Canadian Payroll Provider Wagepoint Names Ben Richmond as Chief Executive Officer
Wagepoint, a leading provider of payroll and HR software for small businesses across Canada, announced the appointment of Ben Richmond as President and Chief Executive Officer. Richmond will also join the company’s Board of Directors and will report to the Board.
Ben Richmond brings over 15 years of leadership experience in global fintech and SaaS, with a strong focus on serving small and medium-sized businesses. Most recently, he was the Managing Director for North America at Xero, where he was responsible for driving growth and operations across the U.S. and Canadian markets, and served as a member of the company’s global executive leadership team.
Originally from New Zealand, Richmond joined Xero in 2013 and held roles spanning 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. He is a Chartered Accountant and holds a Bachelor of Commerce degree in Accounting, Finance, and Information Systems from the University of Canterbury. He has a passion for the Accounting profession and is an advocate for the role Accountants and bookkeepers play with technology to support small business. His efforts to support the profession in Accounting technology and transformation over the years saw him recognized as one of Accounting Today’s Top 100 Most Influential People (2019, 2020), a CPA Practice Advisor 20 Under 40 honoree (2020), and he received the Chartered Accountants Australia and New Zealand Institute of Chartered Accountants Westpac Outstanding New Member of the Year award in 2013.
Richmond’s appointment comes at a pivotal moment as Wagepoint rolls out Wagepoint 2.0 – a modernized payroll platform built to help offer faster processing, improved automation, enhanced compliance tools, and a refreshed user experience. Designed with small businesses and their advisors in mind, Wagepoint 2.0 sets the foundation for the company’s next chapter of innovation and scale.
“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 succeeds Bill Hewitt, who has served as interim CEO since early 2025. Hewitt will continue in his role as Executive Chair and remain on the Board of Directors.
“I’m honored to join Wagepoint at such an exciting time,” said Ben Richmond, President and CEO of Wagepoint. “Small businesses are the backbone of the economy, and Wagepoint has built a strong foundation with its simple, human-focused payroll solutions. 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.”
View the announcement here.
Executive Search Partnership: Wagepoint
Partners Jake Espenlaub and Danny Bolger are proud to have partnered with Wagepoint on this Chief Executive Officer appointment. Learn more about ON Partners by downloading our recent 2025 CEO Report, exploring multi-faceted pathways to the CEO role and 2024 Private Equity Talent Trends Report, which unveils the five key themes reshaping executive talent strategies in private equity.
Wagepoint is a Canadian fintech company on a mission to simplify – and maybe even dare to delight – the payroll experience. Built specifically for small businesses, our software automates the most time-consuming parts of payroll – like wage calculations and tax filings – so that our customers can focus on doing what they love. Founded in 2012, Wagepoint serves over 25,000 small businesses, accountants, and bookkeepers across Canada. Backed by a friendly team, we make payroll magic happen every day. To learn more, visit www.wagepoint.com or follow us @Wagepoint.
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