Pineapple Financial Announces Operational Transformation Strategy and AI-Empowered Sales Expansion; Initiatives Include Reduction in Annualized Costs by More Than $2.5 Million and Launch of AI-Powered Agent Growth Platform

AI Deployment, Agent Onboarding Automation and Permanent Expense Reductions Expected to Improve Operating Leverage and Earnings Durability

Workforce Realignment Significantly Reduces Monthly Cash Burn by More Than 50%

Strengthened Core Mortgage Platform Positions Company for Scalable Growth, AI-Driven Search and Sales Expansion Initiative to Reach 40,000+ Agents Nationwide

Toronto, Ontario--(Newsfile Corp. - March 10, 2026) - Pineapple Financial Inc. (NYSE American: PAPL) ("Pineapple" or the "Company"), a leading fintech platform, today announced a comprehensive operational restructuring as part of its 2026 Core Mortgage Platform strategy. When complete, the structural reset will materially lower the Company's fixed cost base, strengthening operating leverage as Pineapple enters its next phase of execution.

To date, approximately $1.33 million (C$1.8 million) of these annualized cost savings have been implemented and are expected to be reflected in the Company's run-rate by March 31, 2026, with the remaining savings currently being executed. As part of the restructuring, Pineapple is realigning the organization around a leaner, AI-enabled operating model, including a reduction in total headcount by over 60%, alongside reductions across professional services, software, marketing, and other operating expenses. Collectively, these initiatives are expected to reduce annual expenses by more than $2.5 million (C$3.4 million). The program represents a permanent structural reset of the Company's cost base.

"We have structurally lowered our operating cost base entering 2026," said Shubha Dasgupta, Chief Executive Officer of Pineapple Financial. "This is a disciplined reset of our expenses designed to improve operating leverage and earnings durability. Importantly, these changes reflect the implementation of AI technology to replace legacy functions. With this leaner operating model in place, we are positioned on a clear path toward higher EBITDA margins and near-term breakeven on a cash-flow basis, while maintaining the capacity to scale efficiently as volumes recover."

A key driver of these changes is the integration of artificial intelligence across core business functions. Pineapple has deployed AI systems to automate and enhance processes previously performed through legacy staffing structures, including workflow automation, data analysis and reporting, and customer and agent engagement. By embedding AI into its operating infrastructure, the Company has structurally lowered its cost structure while preserving platform capability and scalability.

Building on its AI-enabled operating model, Pineapple is also launching an AI-driven search and sales agent onboarding program designed to accelerate network expansion and platform adoption. The Company is leveraging artificial intelligence to identify, engage and onboard high-performing mortgage professionals more efficiently, while enhancing the recruitment funnel through automated outreach and qualification workflows. As part of this initiative, Pineapple plans to proactively connect with more than 40,000 agents across Canada to expand its national footprint and drive scalable revenue growth. By combining AI-powered operational efficiencies with systematic sales expansion, Pineapple is positioning its platform for disciplined, technology-enabled growth.

With the restructuring largely complete, the Company is focused on execution and unit economics. Pineapple has implemented a recurring operating scorecard to track cost per funded loan, funded loans per operations FTE, software spend per agent, and workflow efficiency metrics.

About Pineapple Financial Inc.
Pineapple Financial Inc. is an award-winning fintech and leading Canadian mortgage brokerage network, focusing on both the long-term success of agents and brokers as well as the overall experience of homeowners. With hundreds of brokers within the network, Pineapple creates cutting-edge cloud-based tools and AI-driven systems to enable its brokers to help Canadians realize their dream of owning a home. Pineapple is active within the community and is proud to sponsor charities across Canada to improve the lives of fellow Canadians.

Safe Harbor Forward-Looking Statements
Certain statements in this announcement are forward-looking statements. These forward-looking statements involve known and unknown risks and uncertainties. They are based on the Company's current expectations and projections about future events that the Company believes may affect its financial condition, results of operations, business strategy and economic needs. Investors can identify these forward-looking statements by words or phrases such as "may," "will," "expect," "anticipate," "aim," "estimate," "intend," "plan," "believe," "is/are likely to," "potential," "continue" or other similar expressions. The Company undertakes no obligation to update or revise publicly any forward-looking statements to reflect subsequent occurring events or circumstances or changes in its expectations that arise after the date hereof, except as may be required by law. These statements are subject to uncertainties and risks including, but not limited to, the uncertainties related to market conditions, fluctuations in the market price of INJ, including risks related to volatility in the price of INJ, the timing and execution of Digital Asset Treasury capital deployment, the treatment of designated cash balances, and the assumptions underlying non-GAAP metrics such as mNAV, and any associated impairment charges that we may incur as a result of a decrease in the market price of INJ below the value at which INJ is carried on our balance sheet; changes in the accounting treatment relating to our INJ holdings; the Company's financial condition, customer acceptance of our INJ treasury strategy, and other factors discussed in the "Risk Factors" section of the registration statements, and periodic reports filed with the SEC. Although the Company believes that the expectations expressed in these forward-looking statements are reasonable, it cannot assure that such expectations will be correct. The Company cautions investors that actual results may differ materially from the anticipated results. It encourages investors to review other factors that may affect its future results in the Company's registration statement and other filings with the SEC. Additional factors are discussed in the Company's filings with the SEC, which are available for review at www.sec.gov.

Media Contact:
KCSA Strategic Communications
Kristin Cwalinski
pineapple@kcsa.com

Investor Relations:
KCSA Strategic Communications
Jack Perkins
pineapple@kcsa.com

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