Pineapple Financial

Pineapple Financial

Pineapple Financial launched in 2015 as a mortgage brokerage in the Greater Toronto Area. Shubha Dasgupta, a former banking executive, built the firm by aggregating independent mortgage agents onto a shared technology stack. The firm now operates across Canada with a network of agents feeding into a proprietary cloud-based platform that handles origination, compliance and borrower communication. The company deploys capital indirectly through its network of agents, who originate residential and commercial mortgages for Canadian borrowers. Pineapple earns fee-based revenue tied to mortgage volumes placed with lending partners that include major Canadian banks and alternative lenders. Its technology platform, PINQ, centralizes client relationship management and automated underwriting workflows for its distributed agent base. The firm also sells ancillary insurance products alongside its core mortgage offerings. In November 2023, Pineapple Financial completed a direct listing on the NYSE American under the ticker PAPL, raising roughly $4 million. Dasgupta stated at the time that the U.S. listing would support expansion into American markets and fund technology development (per public filings, 2023). The firm does not disclose total mortgage origination volumes or the exact size of its agent network as standard operating metrics. Pineapple Financial operates as neither a pure lender nor a pure software company. The firm's hybrid model positions it to earn recurring software-style fees from its agent network while collecting volume-based commissions from lending partners — a structure uncommon among Canadian mortgage businesses, most of which operate as traditional brokerages without their own proprietary technology licensing model.