In this exclusive CanadianSME Small Business Magazine interview, Craig, Founder and CEO of Peloton, shares his journey from engineering complex systems in defense and public sector technology to revolutionizing the payments experience for Canadian small businesses. Drawing on rich experience across both enterprise and entrepreneurial roles, Craig explains how robust design, reliability, and a focus on SMB-specific needs are shaping the future of seamless, secure, and innovative payment solutions nationwide.
Craig is the Founder and CEO at Peloton where he has not only transformed the payments experience for SMBs, but has continued to play a hands-on role in innovation at the company. Prior to founding Peloton, Craig held senior engineering roles at Sierra Systems (now NTT Data), Visiphor Corporation (now I2 Group) – which supplies software products to the criminal justice system – and BAE Systems, one of the world’s largest defense contractors. He has also served as senior technology consultant to Quartech, CGI and Deloitte. His background in serving both the public and private sectors, including in defense, has been key to the success of Peloton here in Canada. Craig immigrated from Australia in 2005.
Peloton has been at the forefront of transforming the payments landscape for small businesses. Can you share what inspired you to create Peloton and how your early experiences in defense and technology shaped your entrepreneurial journey?
Peloton really came out of a mix of frustration and opportunity. Earlier in my career, I worked in defense and large-scale tech — environments where failure isn’t an option. I was often brought in to untangle complex systems and rebuild them so they worked reliably and securely. Those experiences taught me to value structure, precision, and robust design — and it wasn’t difficult to notice the absence of these principles for small businesses payments.
I experienced it firsthand while running a pet supplies store on the side. It was challenging to juggle multiple vendors, disconnected systems, and understand cash flow in real-time. Small business owners spend so much energy just trying to get paid, let alone pay their suppliers — I figured there had to be a better way.
That’s how Peloton started. We wanted to apply the same engineering discipline and design I’d learned in architecting enterprise systems to payments, simplifying and unifying the experience so businesses could focus on running operations instead of managing tools.
The mindset from my early career still shapes how we build today: reliability, security, and scalability first. Ultimately, we’re here to make payments seamless and predictable, so small businesses can spend less time worrying about money and more time focused on growth.
Many small businesses struggle with managing payments and maintaining steady cash flow. From your perspective, what are the biggest challenges SMBs face today in payments, and how is Peloton helping them overcome these obstacles?
Small businesses face three major challenges when it comes to point-of-sale (POS) solutions:
First, fragmented technology. Too often, payments, reporting, and hardware operate in silos—costing time and money when they don’t work together. Small businesses need fully integrated systems that simply work, so they can focus on customers, not connections.
Second, competing in an environment of giants. When companies like Amazon set the standard for seamless payments, small businesses are expected to match that experience. They need enterprise-grade reliability and uptime—without the price tag.
And third, finding a path through the noise. The payments landscape is crowded and confusing, full of similar-sounding options and complex pricing models. Small business owners shouldn’t have to be experts in payments to choose the right solution. They need clear information, transparent pricing, and a partner who can help them navigate what’s right for their business.
At Peloton Technologies, we believe there’s no “off-the-shelf” solution for payments. Every business deserves technology built to fit their needs, backed by reliable support and honest advice.
The payment industry has been evolving rapidly with the growth of digital wallets, open banking, and automation. What top three emerging trends do you believe will most significantly impact small businesses in the next five years?
It is such an exciting time to be in payments because there is so much happening. And much of it will change the game for small business owners. From my perspective, the payments shifts they are mostly likely to feel are stablecoins, open banking and real time payments.
I’ve written about why small businesses should care about stablecoins. These digital tokens—pegged to fiat currencies—are lowering costs and speeding up settlement, especially in cross‐border commerce. For a small business paying suppliers abroad or receiving payments, stablecoins mean less waiting, lower and transparent fees, and better cash‑flow.
Open banking is another big one. More small businesses are directly connecting their bank account data, initiating payments and sharing financial information via APIs. This has huge opportunities to speed up and enhance lending to small business, and it creates opportunities for small business innovation. Adoption among SMEs is now roughly one in five in the UK since open banking launched there in 2018.
At Peloton, we’ve seen firsthand how faster payments boost volume: our customers grow faster when funds arrive sooner. For a small business, getting paid instantly or paying suppliers instantly means you do more business in less time, creating far more value.
Having worked closely with small business clients across Canada, what are some of the most common payment-related questions or concerns you hear from entrepreneurs — and what advice would you offer them?
When I talk with small business owners, the same questions come up again and again.
First, costs and pricing are top-of-mind. Payments can feel opaque— one provider may charge more than another, some costs are fixed and others are variable, and there are multiple participants in the system that makes a payment flow. I try to break down how pricing structures actually work and where the value comes from, whether that’s better uptime, stellar service, or lower risk.
Next, owners want to understand how the technology can help their business. Small businesses want technology that matches their reality, not a scaled-down version of an enterprise tool. Beyond simply taking payments, the right terminal or software can streamline operations, speed up checkout, and simplify reconciliation—all of which save time and money. And the right integrations are key here.
Finally, they ask what’s involved in switching. Many assume it’s a painful process, but it doesn’t have to be. Setup can be seamless and the payoff—better tools, better pricing, better support—is immediate and increasingly beneficial over the long term.
My advice to all entrepreneurs is to think about payments early, reach out to an expert when developing your business plan or prior to committing to any payment technology or vendor.
As a seasoned leader and innovator, what key lessons or insights would you like to share with Canada’s small business community about embracing financial technology and future-proofing their operations?
The most important thing for small businesses to understand is that they have options.
Typically, small businesses have had difficulty getting what they need from large banks, so alternatives have sprung up across the country to help fill that gap. For the most part, these are fintechs and – while they still rely on Canada’s largest banks – they are able to better serve the very diverse needs of small business market, particularly in payments and lending.
My advice would be, if you aren’t getting what you need from your bank, or – if you are simply curious to know if there are better options – you really should be looking at alternative players in the financial services sector. Fintechs bring the same stability and security you require but can improve your experience and the experience you deliver to your clients. Many fintechs are still small businesses, so there is also a real understanding of what it means to operate like one.
