Wealthsimple, the Toronto fintech that serves more than four million Canadians, has introduced Penny, an AI assistant built into its app. It was unveiled on 5 November 2026 at the company's Wealthsimple Presents event in Toronto, one of twelve launches shown that day. Penny is meant for everyday money chores and for trading, and the company says it never moves money, places a trade or takes any action without the client confirming it first.
On the banking side, Penny can prepare e-transfers and wires, pay invoices, track expenses and flag duplicate credit card charges. Self-directed investors can ask it to set up purchases and sales of stocks and ETFs. For bigger goals it plans in steps: told to max out an RRSP by March, it checks the client's linked institutions, sets up recurring investments and adjusts if circumstances change.
“What we’re not advocating is sharing your primary credentials with a third party”
Jordan Deutsch, director of software development, Wealthsimple, to BNN Bloomberg · bnnbloomberg.ca ↗
Privacy limits are part of the design. Penny does not hold a client's SIN or full account numbers, the underlying AI model receives only the data relevant to each request, and the assistant has no access to the wider internet. It lives inside the Wealthsimple app, so there is nothing to share with Siri or Apple Intelligence.
The company is also planning to let clients connect their accounts to ChatGPT and Claude from early 2027, after approval at setup and with extra checks on critical actions. Wealthsimple frames this as a safer, direct connection, and the announcement lands as tech giants push AI further into commerce in Canada and the United States, raising cybersecurity worries.
Illustration accompanying Canadian Press coverage of the AI banking assistant
Image: MoneySense
Penny was the headline of a bigger showcase, the company's fourth. Other launches include the Wealthsimple Pro trading suite and perpetual futures in late November, commission-free CAD options, temporary virtual cards by the end of 2026, and a business credit card with no foreign-exchange fees and 1% cashback plus a rebuilt native app in early 2027. Wealthsimple Pay can also send up to $100,000 instantly between clients, a ceiling the reports put at 33 times a typical big-bank e-Transfer limit. More than 700,000 Canadians registered for the livestream, and the company reports about $169 billion in assets under administration. The reports give no broad availability date for Penny itself.
About Wealthsimple
Wealthsimple is a Toronto-based Canadian online investment and money-management company, founded in September 2014 by Michael Katchen, Brett Huneycutt and Rudy Adler.
It merged with the broker ShareOwner Investments in December 2015, which made it the owner of one of Canada's discount brokerages. In March 2019 it opened its zero-commission Wealthsimple Trade app to the public. In October 2022 it became the first company that is neither a bank nor a credit union to be approved by the Bank of Canada for a direct settlement account, and in 2025 its assets under administration passed C$100 billion.
2014
Founded
The launch also comes as the company reaches new scale. It recently hit a valuation of $13.8 billion in Canadian dollars, and it says clients have traded $24 billion of options since it began offering $0 US options last year. Investor Economics ranked it first in Canada for self-directed trades in the first half of 2026. The event was also held in Vancouver, Montreal and Calgary. Co-founder and chief product officer Brett Huneycutt described the broader aim as making dealings with a bank, or with one's own money, something people are pleasantly surprised by rather than dread.