In this exclusive interview, Jason Leong, CEO and Co-founder of PocketSmith, shares how the company is helping people take control of their finances through intelligent forecasting and personal finance technology. Under his leadership, PocketSmith has grown into a globally recognized fintech platform serving users in more than 190 countries.
Jason discusses how PocketSmith leverages AI, open banking, and financial forecasting to simplify money management. He also shares his perspective on the future of personal finance and how technology is empowering better financial decision-making.
PocketSmith has operated under open banking regimes in the UK, Europe, Australia, and New Zealand. From that global vantage point, what is the single biggest lesson you think Canada should take from markets that are further down the track?
The biggest lesson is that usefulness drives adoption.
Every market we’ve operated in reinforces that point. The UK built world-class open banking infrastructure, but early discussions often focused on metrics like bank switching rather than the practical benefits consumers were experiencing. Australia launched with strong consumer protections, but the cost and complexity of participation made it harder for some fintechs to deliver those benefits at scale. New Zealand had the advantage of learning from both approaches.
The common thread is that people don’t adopt open banking because they care about open banking. They adopt it because it helps them do something they couldn’t do before, or do it more easily.
For most households and small business owners, that means seeing all their accounts in one place, keeping connections reliable, sharing data safely, and gaining better visibility over their finances.
Open banking succeeds when nobody is thinking about open banking at all. They’re simply using products that work, built on secure infrastructure they never have to think about. That’s the standard Canada should aim for: not adoption of a framework, but adoption of useful outcomes.
You’ve argued that if Canada measures open banking primarily by how many people switch banks, it could declare failure on a system that’s actually working. How should success be measured instead, especially for everyday households and small business owners managing both business and family finances?
Success should be measured by consumer outcomes, because that’s what open banking is ultimately for.
The focus on switching comes from viewing open banking primarily as a competition tool: build it, and customers will move between banks. But most people don’t wake up wanting a new bank. They want to understand their finances better, avoid costly mistakes, and make more confident decisions.
So measure the things that matter. Can people see all their accounts in one place, even if they’re spread across multiple institutions? Are connections reliable? Are households identifying unnecessary fees, building savings, and planning further ahead? Is the small business owner spending less of their weekend reconciling accounts and more time running their business?
Those are the outcomes that change lives, and none of them require anyone to switch banks.
There’s an irony here, too. When customers can easily compare products, fees, and performance across institutions, banks have a stronger incentive to compete for the customers they already have. Competition doesn’t just show up as switching; it shows up as better service, better products, and better outcomes.
If Canada measures success solely by bank switching, it risks missing the real value open banking creates.
Many Canadians don’t realize that some of the apps they use today still rely on screen scraping. Why does the shift to secure, permission‑based API access matter so much for privacy, security, and consumer trust—and what does that change look like in practical, day‑to‑day terms?
Screen scraping requires consumers to share their online banking credentials with a third party, which then logs in on their behalf and copies the information it can access. It enabled a generation of innovative financial tools — including ours in markets where no alternative existed — but it was always a workaround rather than a long-term solution.
The challenges are well understood. Connections can be unreliable because they depend on bank websites remaining unchanged. Questions about responsibility and liability can become unclear. Most importantly, it normalises behaviour that runs counter to basic security advice: don’t share your banking credentials.
Secure API-based access changes the model entirely. In practical terms, when you connect an app, you’re redirected to your bank and log in directly with them. The bank then shows exactly what information the app is requesting and asks whether you’d like to grant permission. Your password never leaves the bank, and you can revoke access at any time.
For consumers, that means more reliable connections, fewer interruptions, greater transparency, and stronger protections. Broadly put: instead of giving away multiple copies of your keys, you’re lending keys that you can immediately take back. This puts you firmly in control of your own data.
You often talk about the “Household CFO,” the person quietly running their family’s finances. What becomes possible when secure, consented financial data meets AI for that Household CFO—and where do you think the line should sit between AI‑driven guidance and human judgment in personal finance?
The Household CFO often manages a family’s finances with surprisingly little support. Financial advice is valuable, but for many households it’s simply too expensive or too infrequent to be available when questions arise.
Secure, consented financial data combined with AI changes that. Suddenly, everyone can have access to a patient financial assistant that’s available whenever they need it. Questions that once required an appointment or an hourly fee can be explored in plain language, using your own financial context.
The result isn’t generic advice, but instead, it’s financial information presented in the way that’s most useful to you: personalised, affordable, and available on demand.
That said, the line between AI and human judgement is critical. AI should help people understand their options, not make decisions for them. Its role is to surface insights, explain trade-offs, and help people think more clearly. AI can be incredibly helpful, but it can also make mistakes or present information with misplaced confidence. The final decision should always rest with the human, because it’s their goals, their circumstances, and their tolerance for risk.
That’s a principle we’ve built into PocketSmith’s MCP server: giving people the ability to connect AI tools to their own financial data, while remaining firmly in control of how that data is used.
PocketSmith started as a bootstrapped calendar‑based money tool in Dunedin and now serves more than 370,000 users in over 190 countries, with new features like Files and an MCP server to connect AI tools to personal finance data. What has building globally from New Zealand taught you about serving markets like Canada, and what are you most excited about next for PocketSmith at the intersection of open banking, AI, and everyday financial wellbeing?
Building from New Zealand has taught us that geography matters far less than understanding people’s financial lives. Whether someone is in London, Sydney, or Vancouver, the underlying challenges are remarkably similar: making sense of complexity, planning ahead, and feeling more confident about money.
Canada is particularly interesting because it’s entering a period of significant change with open banking. We’ve seen in Australia and New Zealand that when consumers gain secure access to their financial data, better tools and new forms of competition follow. That’s good for innovation, but more importantly, it’s good for consumers.
What excites me most is the convergence of open banking, AI, and personal financial history. At PocketSmith, we’re building tools that help people turn their financial data into something more useful than a collection of transactions. Features like Files and our MCP server are early steps toward a future where your financial information becomes a trusted, searchable memory that AI can help you understand and act on.
The opportunity isn’t just smarter software. It’s helping people make better decisions, with less effort and more confidence, every day.
Disclaimer:
The views and opinions expressed in this interview are those of the interviewee and do not necessarily reflect the official policy or position of CanadianSME Small Business Magazine. Our platform is dedicated to fostering dialogue and sharing insights that inspire and empower small and medium-sized businesses across Canada.
