Young and Trusted: Designing Canadian Investing for the Great Handover

I've been thinking about this since 2017, when CIBC launched a prepaid credit card that enabled newcomers to Canada to start building credit, with someone who already banked with CIBC vouching for them. It was innovative for the time, a bank designing for a relationship between two people instead of one account holder. The idea came into focus in 2023, with the dawn of AI-powered chatbots, and I've tried to start this article more than once since. But the latest feature releases from Wealthsimple re-triggered me, because some of what I was worried about back then has already arrived.

For a good part of my UX career in the 2010s, working across CIBC, TD and RBC, I could see that an aging population would eventually age out of the digital banking experience. Add to that, the next generation (Gen X and younger) wouldn't have a strong everyday experience in longer-term saving and investing.

Sure, we have investment calculators, and there are stock trading apps. But the task of enabling that transition of wealth is still a wealth-advisor activity. Added to that, a lot of the adults aging out rarely explain where and how their funds are managed.

And the risk is real. Wealth, or the lack of wealth planning, makes this age transition challenging to enable. Emotional equity and trust aren't easy to have when money is the foundation of the conversation.

Before getting into it, where is this coming from? I've spent 10+ years of my career designing marketing websites, web applications, conversion funnels and investing tools for Canadian banks and wealth firms across the industry. These engagements taught me the same lesson from a variety of sides of the transaction. Banking is expected to be a singular experience. Shared accounts are for partners in the same house, and NOT multigenerational, between older parents and adult children, or even through to their next generations.

A handover that changes who the customer is

The reality: a lot of wealth is moving from one generation to the next in Canada right now, and it will keep moving for years. What was last decade's reverse mortgage has become this decade's estate-executor financial headache. And worse, without properly named and co-signed living beneficiary planning, it requires a death certificate to initiate the transition.

Factually, the person who built that money is often in their seventies or eighties, probably not able to log into their accounts online, and unable to get in-branch support because of where the industry is today. And the person receiving it might be in their forties, or their twenties, and might never have stepped into a branch in their life, let alone have the time or capacity to upskill and know the better options for managing their senior parents' finances.

That changes who is on the other end of an investing app. It is no longer one customer with one set of habits. It is a parent who wants to understand exactly what is happening and to feel safe while it happens, and a child who expects the whole thing to work like every other app on their phone. Often it is both of them, looking at the same account, at the same kitchen table.

And in the middle, a banking industry that doesn't enable either of them to have "those conversations" without the account holder exclusively directing the conversation. Again, the cognitive load, the mental acuity and the financial intelligence are not assured. And most financial advisors are not trained on financial continuity or multigenerational challenges.

The top line in all of this: most digital investing products were not designed for that kitchen-table conversation.

Young and trusted, at the same time

For a long time, the market split cleanly: modern and easy, versus the feeling that your money was safe and someone serious was looking after it. But that split is closing.

People now expect both at once. The ease and the speed of the young brands, and the trust, the security and the accountability of the institutions.

Regardless of age or expectation, money management and estate consolidation still need banking infrastructure. A bank that only offers trust will lose the next generation. Meanwhile, a challenger that only offers ease will lose them the first time something goes wrong with real money.

The firms that win the next decade will be the ones that design for financial collaboration between family members and chosen households, enabling multiple family members to take part through the same experiences and screens.

It's bigger than a design problem, and it comes before the technology problem. It's an industry and compliance issue that still hasn't fully started.

What I saw from the inside

At CIBC, the investment calculators lived as separate tools, organized around banking products, levels of investment, or time horizons for access to funds. The innovation was, and is, there. For example, across multiple projects where complex data entry was broken, the digital teams worked to create small, comfortable steps instead of one intimidating form.

The current age of banking is a testament to the fact that people do not want a clever calculator. They want to understand what their banking numbers mean for them, and what to do next.

Banks with disjointed sets of screens are losing out to 360 experiences that graduate users based on their needs (I'm looking at you, Wealthsimple): end-to-end customer workflows where the front-end experience and the back-end data meet. Banking apps that put the tasks people actually came to do first, and remove the drop-down menus and hard-sell banners in front of the user's banking dashboard. Add in accessibility and cognitive load, not as a compliance line item at the end of the project, but as the go-to-market execution.

Next up: accessibility and cognitive load as the strategy

This is the part more product and digital leaders need to hear: make it easier for banking customers to have their safe, shared space. It used to be the branch wicket, and nothing has emerged to replace it.

Think about the kitchen table again. The parent may have changing eyesight, less steady hands, or simply less patience for an interface that keeps moving things around. They used to go to the branch, but now, with advanced age and less mobility, they have fewer options. They might have their adult child trying to navigate on their behalf, reading on a phone. Or even worse, doing so in a hurry, between other things.

Both the senior parent and their adult child are making decisions that matter, about money that took a lifetime to build, with a good dose of emotion and missing context.

Designing for a shared banking experience would be ideal. A design that is easy to see, easy to operate and easy to understand serves both of them. Maybe it's even voice or TV based.

Currently the industry focuses on designs that are dense, clever and full of jargon: big number-goes-up graphs, and detail views with numbers and trends, but not a lot of intelligence on why. This shared view fails everyone involved, and it fails them at the exact moment trust is being decided.

Context and analysis are critical, and hard to govern. Investment advisors are accountable, but not easily found in these everyday or last-minute situations.

It means progressive disclosure, so people see what they need for this step and can go deeper when they want to. And it means fewer decisions per screen, because every extra choice is a small tax on attention, and attention is the thing people have least of when the stakes are high.

In practice, that means meeting WCAG as a floor, not a finish line. It means plain language, especially around fees, risk and tax. And in the future, it should be a shared intelligence between everyone involved.

The big reveal is AI and voice UX

When I first sketched this idea of a shared investment space, AI assistants and voice interfaces were a far-away idea: an ever-patient, persistent hand holding the conversation and the context. And since 2017, when I started working on investment chatbot proofs of concept, it felt like a few years away.

It is not anymore. Customers will soon ask an app, out loud, whether they can afford to help their kid with a financial payment, or what happens to an account when a parent dies. That is the necessary opportunity, and a real risk. We are STILL discovering whether a voice that sounds confident is the same as advice that is right. And in a regulated industry, the difference is the whole game.

The trust work has to be designed before the features ship. When is the assistant explaining, and when is it advising? When, and how, does a licensed person step in? What gets written down, and who can see it later? How does the customer correct it when it gets something wrong?

I build with these tools every day, and the pattern that works is the same one I would want at a bank: let the machine do the patient, repetitive explaining, and keep a person in the loop wherever the money and the rules are.

What to plan for in the next five to eight years

If I were sitting with the digital leadership of a Canadian bank or wealth firm today, this is what I would put on the whiteboard.

1. Design for the kitchen table. Two generations, one account, often one screen. Shared access, clear roles, and language both of them understand.
2. Hold both bars at once. Challenger-level ease and bank-level trust in the same flow. Test for both with real customers.
3. Treat accessibility as product strategy. WCAG as the floor, plain language everywhere, and a hard look at how many decisions each screen asks for.
4. Connect the tools into a service. Every answer should lead to a natural next step, not a dead end.
5. Design the trust before the AI. Decide what the assistant explains, what it never decides, and when a person steps in, before you ship it.
6. Keep the data and the decisions visible. People trust what they can see and correct. Show your work.

None of this is exotic. It is careful, human-centred design applied to a moment that does not come around often. The handover is happening whether our products are ready or not. I would rather they were ready.