In 2023, Pineapple secured a spot on The Globe and Mail’s annual list of Canada’s fastest-growing companies, posting a three-year growth rate of nearly 1,500% before going public on NYSE American.
The Canadian firm develops cloud-based tools and AI-driven systems which enable mortgage brokers to help Canadians buy a home.
In 2024, Pineapple Financial predicted further growth and profitability.
Revenues did grow, but years on, profit remains elusive, and the publicly traded firm’s stock price has suffered as a result, with shares trading from a 2023 high of more than $50 down to less than $1 today.
Last year, the Toronto fintech garnered a $100 million private placement, which spurred a massive surge in share price—from just 50 cents in May to over $7 following the September announcement.
The spike was brief, however, with shares in PAPL steadily eroding since then, returning to sub-$1 in January.
This month, Pineapple revealed that its Board of Directors has authorized a share repurchase program for up to US$3M of the Company’s common shares in the open market.
The decision to do so, says chief executive officer Shubha Dasgupta, “reflects our conviction in Pineapple’s long-term strategy and the strength of the operating model we’ve built.”
Dasgupta and the Board remain convinced that “our current market valuation does not fully reflect the progress we’ve made across our mortgage platform, our data and tokenization initiatives, and our Digital Asset Treasury.”
“We believe that … This authorization will provide flexibility to deploy capital opportunistically when it enhances long-term shareholder value, while we remain focused on execution, liquidity discipline, and building a more durable earnings profile over time,” the CEO stated.
Pineapple intends to begin repurchasing shares in the first half of 2026, according to Dasgupta, who says the timing, price, and volume of repurchases will be at the discretion of the company based on market conditions and other factors.
Pineapple was founded in 2015 by Dasgupta alongside Kendall Marin and Drew Green.
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