Leadership lessons: The path from VP of Finance to President

We wrapped up 2024 – a year of remarkable growth and change – by announcing Michael Penman as Payworks’ new President… so we figured we’d kick off 2025 by re-introducing him! Mike joined Payworks in 2016 as Vice President of Finance, subsequently moving into roles as Chief Financial Officer and Chief Operating Officer. He’s also alternatively known around here as Penman, “the numbers guy,” and the unequivocal tallest in the office.

We sat down with Mike to learn more about his career journey thus far, find out what’s been the most meaningful to him along the way, and even have some “fun with numbers” (a Penman classic).

Photo: Michael Penman, President of Payworks.

Can you tell us about your career path? Was company leadership always your goal?

I started my career working at Deloitte, where I became what’s now known as a CPA CA and spent a few years before moving to an international payroll provider. There, I worked for over a decade in a variety of roles in the finance department and with business operations leaders. Once I’d left that organization, the leadership team at Payworks recruited me to become VP of Finance… and here we are!

But no – the role of President really wasn’t the goal; rather, my goal’s always been to have a fruitful career enjoying my work and making a difference. After all, at one point, I thought that I’d be a partner providing taxation and accounting advice to clients! No matter where I’ve been or what team I’ve served, I feel fortunate to say that I’m working towards my goal every day.

What have you taken away from your first few months leading Payworks?

It’s interesting, because no two days are exactly the same. You get to have different interactions and hopefully help develop other people and see their success. It’s also been fun to get to know the broader team a bit better! Payworks is the kind of place where you can feel comfortable saying hello to or joking with pretty much anyone in the hallway.

There are a lot of people at Payworks now. I’ve always been aware of the complexities of employing 600 people and balancing the multitude of departments and projects that goes along with that. But I didn’t fully appreciate how many spinning plates there are and the amount of time it takes to stay current and make sure that busy people are connecting with each other in the right ways.

What does your average weekday look like now? Do you have any routines to get you started or to help you relax after you’re done?

Well, like I said earlier, no two days are exactly the same… but there’s one part of the routine that’s non-negotiable: I start off having breakfast with the family before heading to the office.

Once I’m in, I get up-to-date on the news and typically have five to six one-on-one and team meetings each day. In between, I’ll do some walk-ins on a couple of floors, just to see people and to get a sense of how things are going and they’re feeling. I’ll head out to make it home for dinner with my family, and then catch up on emails after the kids go to bed because I feel better starting the next day with a clean slate!

In the off hours, when the weather’s keeping me indoors, I typically try to have some sort of DIY project on-the-go at home – it’s my form of meditation. Is that weird? “Hey, what’s your meditation?” “More work!” But it’s a different form of work, so it feels like a welcome distraction.

Now that you’re the President of Payworks, is there anything from your previous roles that you do or don’t miss doing?

In my first years as CFO, I’d be teased by my friends when I’d get a phone call on the golf course to leave and turn off the hot water tank at work (or whatever the situation may have been). I wasn’t the first call, but sometimes I was the first to pick up – and it’s my responsibility to make sure that our assets are protected. Nowadays, I’m still on the call list, but I’m pleased to have moved further down!

However, there are times when I do miss getting lost in the details and the execution, rather than at the strategic leadership level. Even in my pre-Payworks days, I took great satisfaction from working through an accounting or math problem. With that said, I still carryover some of that work today, but now I get called upon more for advice – like “it’s a new tax year, what’s changing now?” So I’m still using the same knowledge; it’s just in a different way.

You’ve been part of the Payworks leadership team for the past nine years - what are you most proud of the company having accomplished?

Hitting milestones makes me feel proud and reminds me of what’s been accomplished – like when we passed 500 employees, and I could take a moment to recognize the size and scale of that!

I’m also proud of how much we’ve given back to the community and the impact that has – on both a national scale and grassroots level. I love to see Payworks at a community event, and to hear my kids scream and shout when they see the logo. It inspires a lot of great conversations.

And of course, I’m also proud of Payworks’ 2024 selection by Deluxe Canada as its exclusive Canadian payroll conversion and referral partner. We onboarded almost 9,000 clients on top of our normal business and we did it even better than we could have anticipated, thanks to the tremendous skills and dedication of our whole team.

Photo: Michael Penman with Barb Gamey, Co-Founder and JP Perron, Retired CEO at the Payworks Way Grand Opening in 2024.

Are there any “fun numbers” you’d like to share?

Would I ever!

• I’ve been part of five office renovations/openings/developments, including Vancouver, Calgary, Toronto, Montréal and Winnipeg.
• When I joined the company, Payworks employed 197 people – and now we’re at over 600! We’ve also added six new departments over the past nine years.
• The year I joined the business, we were serving 14,000 clients across Canada – and now we’re at 43,000!
• In 2024, 250+ Payworks employees volunteered more than 2,200 hours to Pay it Forward in their communities.
• We proudly support more than 250 organizations across Canada through local sponsorship, volunteering, investment and employee-initiated giving.
• We’ve been named one of Canada’s Best Managed Companies for the past 12 consecutive years.

Let’s wrap things up with a lightning round! Here are five quick questions to close out the conversation:

1. When you were a child, what did you want to be when you grew up?

   An investment banker or an engineer.

2. Have you received any advice that resonated with you?

   Don’t sweat the small stuff – and remember that family’s always first.

3. Are you listening to any leadership or business podcasts right now?

   Sometimes I listen to the Malcolm Gladwell Revisionist History podcast, and a friend suggested that I listen to the Acquired podcast, where they do a deep dive into how businesses become successful. The IKEA and Costco episodes were both really interesting to see how people changed the entire industry when it comes to how things go to market.

4. Are there any leaders whose stories you’ve followed?

   I’ve read about some people who aren’t necessarily leaders, but who’ve been able to accomplish a lot – like Warren Buffett, the Oracle of Omaha, who built an empire and is still doing it in his 90s. He’s planning on donating most of his wealth and is working just for the joy of doing it, so it’s a very interesting story.

   I’ve also watched documentaries on Winston Churchill, not necessarily because of his politics, but because of his story of successes and failures. Every time he failed, he used it as a means of learning and got back up again.

5. At our past President’s Circle draw events, we’ve had a tradition where the leadership team dresses up in silly costumes to announce the winners. Do you have a favourite costume… and will the tradition continue now that you’re President?

   The tradition will continue, but in full declaration and unfortunately for our Marketing team, I won’t bring the same acting chops as my predecessor. I think it’s part of our identity and it’s good to have some fun and laugh at yourself, especially because it’s really about recognizing people and drumming up excitement for the trip.

   For my favourite costume, it doesn’t actually fit, but I still wear the Yeti costume for Halloween when I trick or treat with the kids. I’ve worn it twice now outside of work! I wouldn’t say that the leprechaun one was a personal favourite, though.

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