Here are 1-3 brief analogies to describe Pineapple Financial (PTIV):

• Shopify for mortgage brokers: Just as Shopify provides a comprehensive platform for businesses to run their e-commerce operations, Pineapple Financial offers the MyPineapple technology platform and brokerage services to empower Canadian mortgage agents and brokerages to operate more efficiently and scale their businesses.
• Salesforce for the mortgage industry: Similar to how Salesforce provides cloud-based CRM and business solutions across various industries, Pineapple Financial's MyPineapple platform, built on Salesforce, offers specialized data management, lead generation, CRM, and back-office support tools tailored specifically for mortgage professionals.

• Mortgage Brokerage Services: Provides services for residential and commercial mortgage opportunities to Canadian mortgage agents, brokers, brokerages, and consumers.
• Mortgage Technology Solutions (MyPineapple): Offers a proprietary cloud-based platform for data management, CRM, lead generation, and workflow automation designed for mortgage professionals.
• Brokerage Back Office & Pre-Underwriting Support: Delivers essential administrative and pre-underwriting assistance to Canadian mortgage brokerages.
• Affiliation (White-Labeling) Programs: Enables licensed mortgage brokers to market and sell mortgages under their own brand name using Pineapple Financial's systems.

Pineapple Financial (PTIV) primarily serves other businesses and professionals within the Canadian mortgage industry. While the company does not list specific customer company names, its customer base can be categorized as follows:

• Canadian Mortgage Brokerages: These are companies that receive back-office services, pre-underwriting support, and proprietary technology solutions (MyPineapple) from Pineapple Financial to enhance their operations and efficiency.
• Licensed Mortgage Agents, Brokers, and Sub-Brokers: These individual professionals utilize Pineapple Financial's mortgage brokerage services and technology solutions, including the MyPineapple platform, for real-time data management, lead generation, customer relationship management, direct underwriting support, and educational resources.
• Affiliate Brokers: These are licensed mortgage brokers who enter into affiliation agreements with Pineapple Financial, leveraging the company's services for joint marketing and "white labeling" of mortgage products under their own company name.

Salesforce.com, Inc. (CRM)

Equifax (EFX)

OneSpan (OSPN)

Alphabet Inc. (GOOGL)

Filogix

Shubha Dasgupta, Chief Executive Officer, Co-Founder & Director

Shubha Dasgupta is a Co-Founder and the Chief Executive Officer of Pineapple Financial Inc..

Usman Maher, Chief Financial Officer and Chief Strategy Officer

Usman Maher was appointed Chief Financial Officer and Chief Strategy Officer of Pineapple Financial Inc. effective October 15, 2026.. He has over a decade of experience in private equity, special situations credit, and high-growth fintech. Prior to joining Pineapple Financial (Pentiv), he was the Senior Director of Strategic Finance at SoFi, where he established the finance function for the company's member platform. Maher is a CFA charterholder since 2011 and holds an M.B.A. from the University of Chicago Booth School of Business.

Kendall Marin, Chief Operating Officer/President, Co-Founder & Director

Kendall Marin is a Co-Founder, President, and Chief Operating Officer of Pineapple Financial Inc..

Sarfraz Habib, Chief Accounting Officer and Controller

Sarfraz Habib previously served as the Chief Financial Officer of Pineapple Financial Inc. Effective October 15, 2026, he transitioned to the role of Chief Accounting Officer and Controller.

Drew Green, Chairman & Co-Founder

Drew Green is a Co-Founder and the Chairman of the Board of Pineapple Financial Inc..

Key Business Risks for Pineapple Financial Inc. (PTIV)

1. High Dependence on Proprietary Technology and Key Third-Party Integrations: Pineapple Financial's core "Brokerage Services" are heavily reliant on its proprietary MyPineapple technology, which is described as being "at the heart of our Brokerage Services" and "built with proprietary code." Furthermore, MyPineapple is explicitly stated to be "backed by Salesforce.com, Inc. ("Salesforce"), pursuant to the Salesforce Agreement," and integrates with other essential third-party services such as Equifax, OneSpan, G Suite, and Filogix. Any disruption to the Salesforce agreement, issues with the performance or availability of Salesforce's services or other integrated platforms, or challenges in the continued development and maintenance of MyPineapple, could severely impair the company's ability to deliver its primary offerings and undermine its operational capabilities.

2. Ability to Sustain Competitive Advantage in a Technology-Driven Market: The company's business model is predicated on the belief that its data-driven systems and cloud-based tools offer "competitive advantages in the Canadian mortgage industry relative to alternative mortgage broker arrangements." In a dynamic and evolving mortgage technology and brokerage market, there is a continuous risk that competitors could develop similar or superior technological platforms or business models. The erosion of Pineapple Financial's technological edge and competitive differentiation could significantly impact its ability to attract and retain agents, brokers, and consumers, thereby affecting its revenue growth and market position.

3. Regulatory Compliance and Licensing Across Multiple Canadian Jurisdictions: Pineapple Financial operates, or plans to operate, across 13 Canadian provinces and territories, having received approval from "each of the applicable provincial mortgage regulators." The Canadian mortgage industry is subject to stringent and diverse provincial regulatory frameworks. The risk exists that changes in these various provincial mortgage regulations, the introduction of new compliance requirements, or challenges in obtaining, maintaining, or renewing necessary licenses and approvals across its multiple operating jurisdictions could impose significant operational burdens, increase compliance costs, or restrict the company's ability to operate and expand in certain regions.

Pineapple Financial Inc. (PTIV) operates in the Canadian mortgage market, offering mortgage brokerage services and proprietary technology solutions to various stakeholders in the industry. The company's addressable markets are primarily within Canada.

The key addressable markets for Pineapple Financial's main products and services are:

• Canadian Mortgage Brokerage Industry: The Canada Mortgage/loan Brokers Market reached an estimated USD 778.56 million in 2025. This market is projected to grow at a Compound Annual Growth Rate (CAGR) of 4.92% to reach USD 989.65 million by 2030. Residential mortgages constituted 74.5% of this market in 2024, and the residential segment alone is expected to increase by USD 158 million between 2025 and 2030. In 2025, the overall share of new mortgages obtained through a broker in Canada reached 38%.
• Canadian Digital Mortgage Software Market (Mortgage Technology Solutions): The Canadian market for digital mortgage software was valued at approximately USD 343.0 million in 2025 and is projected to grow to USD 1,880.0 million by 2034, demonstrating a CAGR of 20.79%. Another estimate places the Canadian market size at USD 171.0 million in 2025, forecasted to reach USD 926.0 million by 2034 with a CAGR of 20.58%. More broadly, the Canadian fintech market, which encompasses mortgage technology, reached USD 5.1 billion in 2025 and is projected to grow to USD 19.3 billion by 2034, at a 15.55% CAGR. Broader estimates for the Canadian fintech market in 2025 are around USD 10.2 billion.

While Pineapple Financial Inc. has also recently engaged in a Digital Asset Treasury strategy and tokenized mortgage data initiatives, a specific addressable market size for "tokenized mortgage data" or "onchain finance" within Canada could not be identified from the available information.

Here are 3-5 expected drivers of future revenue growth for Pineapple Financial (PTIV) over the next 2-3 years:

1. Expansion into the U.S. Market with the Pentiv Intelligence Platform: Pineapple Financial, which has rebranded as Pentiv, is strategically expanding into the U.S. market. This expansion is driven by an upgraded intelligence platform designed for mortgage professionals, aiming to commercialize its technology beyond its existing Canadian brokerage network. This initiative positions the company as a software and intelligence provider, adopting an asset-light, recurring-revenue model.
2. AI-Powered Agent Growth and Network Expansion in Canada: The company is leveraging artificial intelligence to efficiently identify, engage, and onboard high-performing mortgage professionals. Pineapple plans to proactively connect with more than 40,000 agents across Canada, a move intended to expand its national footprint and foster scalable revenue growth.
3. Monetization of Mortgage Data through Tokenization and Data Marketplace: In December 2025, Pineapple launched a mortgage tokenization platform that converts real-world mortgage records into secure, programmable digital assets on the Injective blockchain. The company intends to migrate its entire historical portfolio of over 29,000 funded mortgages, valued at approximately $13.7 billion CAD, and continuously add new originations. This strategy is expected to lead to new commercial products, including a Mortgage Data Marketplace, offering institutions improved benchmarking and market intelligence.
4. Significant Canadian Mortgage Renewal Wave: Pineapple Financial anticipates a substantial wave of mortgage renewals in Canada, with over 1 million mortgages, representing 17% of all outstanding mortgages, scheduled for renewal this year. This cycle is expected to generate a recurring pipeline of refinance and renewal activity, driving expansion over the next 24 months.
5. Expansion of Pineapple Insurance Offering: In May 2025, Pineapple Financial partnered with CPP to broaden its Pineapple Insurance offering. This expansion aims to tap into a multi-billion dollar opportunity in life, creditor, and disability insurance for its mortgage clients.

Share Repurchases

• Pineapple Financial (PTIV) authorized an expanded share repurchase program of up to $15 million in April 2026.
• This authorization includes an initial $3 million tranche currently being executed in the open market.
• As of May 20, 2026, Pineapple Financial (PTIV) had repurchased approximately 554,581 common shares, representing about $657,060.29 of capital deployed.

Share Issuance

• In May 2025, Pineapple Financial (PTIV) closed a public offering with aggregate gross proceeds of $1,500,000, issuing 10,000,000 units at $0.15 per unit, each consisting of one common share and one warrant.
• The company executed a 1-for-20 reverse stock split on July 16, 2025.
• The number of shares outstanding for Pineapple Financial (PTIV) increased by 1840.56% in 2026, reaching 26.08 million shares compared to 1.34 million in 2025.

Inbound Investments

• Subsequent to its fiscal year ended August 31, 2025, Pineapple Financial (PTIV) launched its $100 million Injective Digital Asset Treasury (DAT) strategy, with the Injective Foundation and its co-founders personally investing in the initiative at a premium.
• Additional anchor investors in the DAT strategy include FalconX, Monarq Asset Management, Canary Capital, and Kraken.
• Pineapple Financial (PTIV) deepened its strategic relationship with Canary Capital in April 2026.

Outbound Investments

• Pineapple Financial (PTIV) launched a $100 million Injective Digital Asset Treasury (DAT) strategy, positioning itself as a publicly traded holder of INJ tokens and other digital assets to generate sustainable yield and enhance its balance sheet.

Capital Expenditures

• In the 12 months prior to October 24, 2026, Pineapple Financial (PTIV) reported capital expenditures of -$1,944.