Pine

Pine was founded in mid-2021 in Toronto by CEO Justin Herlick and CTO Jonathan Shih to digitize and simplify the Canadian home-financing process. Herlick previously worked at Blend, the Silicon Valley-based digital mortgage/lending software company (itself a long-time Greylock portfolio company that later went public), and that experience both shaped Pine's product vision and helped attract a syndicate of Blend investors to Pine's cap table, most notably Greylock, which led both of Pine's first two rounds. Pine raised a $6 million CAD seed round in 2021 (led by Greylock, with Original Capital, BoxGroup, Ludlow Ventures, and Thomvest -- all prior Blend backers -- also participating) and then a $21 million CAD Series A that closed in March 2022, also led by Greylock, with continued participation from Montreal's Inovia Capital plus new investors Global Founders Capital (Slack, Facebook, LinkedIn, Trivago, Revolut, Brex) and Intact Ventures. Pine came out of stealth publicly on May 31, 2022, launching in Ontario with a stated goal of becoming the "Wealthsimple for home buying," and said it planned to expand across Canada within the year. At the time, Pine operated as a mortgage broker with a single lending partner (undisclosed) and said it was working toward becoming a CMHC-approved lender.

In October 2023, when announcing its acquisition of proptech peer Properly, Pine disclosed that it had also quietly closed an additional $13 million CAD in previously unannounced financing in mid-2022 (mostly equity at Series A terms, plus some venture debt) from new investor Garage Capital and existing backers, bringing its total Series A size to $34 million CAD. By that point Pine had become a licensed direct lender (in all provinces except Quebec), which Herlick said had roughly doubled Pine's revenue per customer. The Properly acquisition -- an all-cash deal that closed in September 2023 after a roughly six-week bidding process (Properly had retained Raymond James to run a sale process) -- gave Pine ownership of Properly's Canadian real estate brokerages, home-search/discovery portal, and associated IP and equity, while a separate, concurrent transaction saw Properly's remaining cash/balance sheet assets (and the IP for its old "Sale Assurance" home-sale-guarantee product) sold to U.S. proptech company Compass; Properly's own founders/execs (CEO Anshul Ruparell, Sheldon McCormick, Craig Dunk) did not join Pine, though some of Properly's team did. Pine's stated rationale was to move "upstream" in the home-buying journey and build what it hoped could become Canada's leading real-estate information/listings destination (unlike the U.S., no single site like Zillow dominates the Canadian market).

Pine continued raising smaller, largely un-trumpeted tranches of capital to fund this expansion: $5 million CAD in venture debt from Silicon Valley Bank in early 2023, and (per BetaKit's June 2025 reporting) a further ~$23 million CAD in combined equity and SAFE financing from existing investors -- reported as including roughly $6.8 million in 2022-vintage equity (at Series A terms) and $13.7 million in SAFEs raised in fall 2024 -- led by Inovia Capital, Intact Ventures, and Greylock, with new participation from Wischoff Ventures, Position Ventures, and MetaProp. (Note: BetaKit's own disclosed figures for this SAFE/equity extension have some internal inconsistency/overlap between its October 2023 and June 2025 articles -- e.g., whether the $6.8M-$13M 2022 extension is counted once or twice across reports -- so the exact cumulative total should be treated as approximate; publicly confirmed, non-overlapping tranches sum to roughly $58-59 million CAD (~$43M USD) across seed, Series A, Series A extension, venture debt, and SAFE financing.) Pine has said this capital was raised largely to hit growth milestones ahead of a planned, larger Series B, which as of mid-2025 had not yet been raised; Herlick said Pine was not actively fundraising and had multiple years of runway.

Business model

Direct-to-consumer fintech that operates as a licensed digital mortgage lender/broker and, since 2023, also as a real estate search/brokerage platform (Pine Homes, built on the acquired Properly technology). Also powers a co-branded, white-label mortgage product for partner Wealthsimple (B2B2C).

Revenue from mortgage origination (interest rate spread/lender economics as a direct lender, and broker commissions where it places loans with partner lenders), plus real estate brokerage-related revenue from its Properly/Pine Homes business; CEO Justin Herlick said in 2023 that direct lending roughly doubled Pine's revenue per customer.