On the TechTO stage ×4
Founder Journey ft. Wayne Pommen
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Canadian Fintech Exit to Affirm: Advice for Founders
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Gauging Opportunity & Success in Rebranding | Wayne Pommen
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Scaling a Fintech in Canada | Wayne Pommen
Watch on YouTube ↗First seen on the TechTO stage in 2021. Every talk is searchable — ask the archive about Wayne ↗
In their words
This is the best time in history to start companies. The tools, the low cost of doing so, the availability of capital — what better time to be alive as an entrepreneur than 2026?
We should have pushed harder, bigger, sooner. There were times where we were too cautious... If we had been thinking bigger sooner, we actually could have been much farther along in the time that we had.
Getting the culture right and getting the operating rhythm right early pays huge dividends as it scales. That sort of cultural DNA of your company echoes in eternity — you want to think a lot about how to get that right in the early going.
We did just under $6 million of loans and generated about $800,000 of revenue. Five years later when we sold to Affirm, we had 220 million of volume and about 20 million of revenue, and the team went from like five to 200 in that time.
It's one of those paradoxes of building companies. The pitch deck you put together is gorgeous, right? Up and to the right. Look at the volume. Look at the revenue. Look at the users. Look at the engagement. Oh my god, where do I write my check? Inside, total chaos. I've had people come to me in tears being like, the customer service backlog is so large, I have no idea how we are going to deal with this.
Maybe you need to know your moment and say, am I going to put it all on red and keep going here, or is the smart thing for us to do to become part of somebody else's story?
I always felt like I'm a little bit of a fish out of water as a private equity investor and if I ever got the chance to operate something or lead something, I would like to do that.
You have to have a growth mindset, right? You have to believe you're going to be getting better in the future and you have to overcome a lot of adversity and failure and you have to be comfortable with that.
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Quick answers
How did Wayne Pommen get to Affirm?
After consulting and private equity, he found a five-employee point-of-sale lending business inside HealthSmart Financial Services, partnered with its original founders, spun it out, and became CEO and the sixth employee. As PayBright it grew quickly from 2016 to 2021, and Affirm acquired it in January 2021, right before Affirm's IPO. He has stayed five and a half years, most of that time as Chief Revenue Officer.
How big is Affirm in Canada?
About 20,000 merchants and ballpark $2 billion in annual volume, growing quickly year over year — over 8 million Canadian consumers have come through the platform, and Shop Pay Installments launched in Canada a few months before this talk. Penetration still trails the US because e-commerce took hold more slowly and Canadians keep long-standing bank relationships, with what he calls the highest credit card penetration in the world.
What is his advice for Canadian fintech founders?
Start today, not tomorrow, and aim high — you can build a global player from Toronto. Get a co-founder, pick investors with founders or operators on the team, and go to market through partners (the embedded finance playbook) rather than expensive direct-to-consumer, unless you can raise hundreds of millions like Wealthsimple. He sees openings in open banking, stablecoins, and the real-time rail.