Ben Richmond joined Wagepoint as CEO last August, stepping into a company that was in the middle of some big changes. New platform, new direction, a lot of expectations from a loyal community of customers and partners who’ve been with us for years.
We wanted to give you a chance to hear from him – about what drew him to Wagepoint in the first place, what he’s discovered along the way, and what he’s building toward.
Here’s what he shared.
What originally drew you to Wagepoint? And now that you’re six months in, how was your perspective changed?
Ben:
My whole career has been around small business. My family were small business owners, and I grew up seeing the stress—especially around payroll. I actually used to run payroll for my grandparents when they went on holiday. So I’ve seen firsthand how critical it is, and how stressful it can be when it goes wrong. That’s what pulled me into accounting and bookkeeping, and eventually to Xero.
During my time there, Wagepoint was always a close partner. So I already knew they’d built something strong—something small businesses and firms across Canada trust and rely on. What excited me about joining was really the opportunity ahead. Cloud payroll adoption is still early here. There’s a huge market, a strong partner ecosystem, and so much room to grow.
Six months in, I can honestly say I’m more energized than when I joined.
What felt familiar when you stepped into the role, and what caught you off guard?
Ben:
A lot felt familiar. Canada has an incredible community of accountants and bookkeepers, many I’ve worked with for a long time. I recognized that passion for serving business owners, for doing things properly, right away.
What stood out was the culture here. It’s human. It’s friendly. People genuinely care. You see it in how teams show up for customers and partners.
Look, we’re not perfect. But when we mess something up, people rally to fix it. And we have this strong, loyal base of accountants and bookkeepers who want us to succeed and who absolutely hold us accountable when we don’t. That’s what real partnership looks like.
You’ve spent years working closely with bookkeepers and accountants. What do you think the industry gets wrong about what they actually need?
Ben:
I think the biggest one is understanding who you’re serving. Software companies in our space focus on selling to small businesses, but accountants use the same tools to support their clients. It creates confusion about who the real customer is.
For me, it’s both. Small businesses didn’t start their company because they love payroll. It’s scary, compliance-filled, pressure-filled. They just want it handled.
That’s where bookkeepers and accountants come in. They’re critical to making that happen. So we need to set them up to do more with less. If a firm can run payroll for more clients with the same team because the technology got better—that’s real impact.
And it matters because small business is lonely. Most owners don’t have a finance department or an IT team. They’re out there on their own. The right partner alongside the right technology makes a huge difference.
From your perspective now, what makes Wagepoint genuinely different in the Canadian payroll landscape?
Ben:
We’re built in Canada, for Canada. And there honestly aren’t many players who can say that.
We’re also intentional about who we’re building for. We’re not trying to be everything to everyone. We have customers with larger teams, but we’re laser focused on being great for businesses with one to twenty employees.
That focus keeps the platform simple and easy. We don’t over-function it, we don’t bloat it with stuff people don’t need. And it matters because there are over a million small businesses in Canada in that segment, and only about 30 to 40% have moved to cloud payroll. That discipline is a big part of why Wagepoint feels the way it does.
Where do you see the biggest opportunities ahead?
Ben:
For me, it starts with nailing the basics. Sometimes the biggest impact comes from things that don’t look flashy at all—a small reporting change or a smoother workflow—but they make a huge difference day to day.
The big opportunity is where we’re headed with the platform. We’re close to having one of Canada’s most modern payroll infrastructures, built from scratch with all the learnings from the first platform. That means we’ll be able to move faster on things like AI—smart AI that actually helps—and accelerate a mobile-first experience in ways we couldn’t with an older platform.
We think a lot about where technology can genuinely help. Helping businesses owners stay compliant. Helping partners manage more payroll efficiently. It’s not about adding features just to add them. It’s about solving real problems.
We just refreshed the brand—new logo, colors, updated look and feel. How should people think about that change?
Ben:
It’s an evolution, not a revolution. We’re keeping the fun, friendly, human stuff that people love, but the brand is growing up a bit. It’s cleaner, more polished, more modern and it reflects who we actually are today.
It’s not just a lick of paint. It represents where we’re headed, while still honouring where the company has come from and the community that’s at the core of it.
Any final reflections you’d like to leave with the Wagepoint community?
Ben:
Accountants and bookkeepers are absolutely core to what we’re doing, and we share this real passion for small business. We want to make payroll easy for businesses—back of mind, they can just trust it’s happening.
I’m proud of what’s been built here. It’s no small feat to get to where Wagepoint is today. And I’m eager to build on that with our teams, our partners, and our clients. We truly want to be the household name for small business payroll in Canada. There’s so much runway ahead, and I’m honoured to be part of it.
Six months into Ben’s leadership, Wagepoint is entering its next chapter–starting with a fresh new look. Learn more about the brand refresh here.
