🔎 Spotlight #7: Inside Pine
A mortgage experience so smooth, you might actually enjoy it
The origin story: Making mortgages make sense
Pine was founded by Justin Herlick and Jonathan Shih, two sharp minds who believed the mortgage experience didn’t need to be stuck in the past. They saw an industry that was overly complex, slow-moving, and built around lenders, not customers. So they flipped the script.
The result is Pine: a digital-first mortgage platform that simplifies everything from pre-approval to closing. Whether you're a first-time homebuyer or refinancing, Pine wraps the full experience into a clean, modern, and personalized platform.
Funny enough, I first heard about Pine through my alma mater. Justin went to Queen’s, and the campus buzz was real. It’s been exciting to watch that early momentum evolve into one of Canada’s fastest-growing fintechs.
What’s fresh in Pine’s forest 🌲
Pine recently crossed a big milestone: over $1 billion CAD in managed mortgages. And they’re not slowing down.
Just a little while ago in June, they launched a suite of new tools to help Canadians not only buy homes but manage the whole homeownership lifecycle. This includes:
Mortgage renewals and refinances, made simple
A new marketplace of real estate partners and resources
Smarter pre-approvals and real-time updates for buyers
It’s all about empowering the modern buyer. They’re building a full-stack experience around trust, speed, and ease. Check out the BetaKit article here to learn more.
Funding and team at a glance
💰 Raised over $27 million CAD across Seed and Series A
🧠 Backed by Greylock, iNovia, Intact Ventures, and others
🌱 Team of 70+ and growing
🏠 HQ in Toronto, with remote-friendly roles
🌐 Website: pine.ca
My experience with Pine
While I haven’t worked or chatted with anyone at Pine, I’ve followed their journey since day one and continue to be impressed. I’ve also spoken to a few folks who have worked with them or gone through the product as customers, and the consensus is clear: this team listens.
They’re close to the customer, iterate fast, and hold a high bar internally. That kind of culture tends to create great products. As someone who's been actively looking to buy a home in Toronto, I’ve felt the frustration firsthand. The mortgage process often feels like it was designed in a different era being full of paperwork, slow timelines, and limited transparency.
That’s why what Pine is building really resonates with me. They’re taking something traditionally stressful and confusing, and turning it into something streamlined, digital, and actually empowering. I can see how this kind of experience could completely reshape the space for the next generation of homebuyers. A common trend I’m seeing in the startup space is taking age-old industries (banking, maintenance, hospitality, etc.) and giving them a facelift, and Pine is no exception.
Who else is in the mortgage tech mix?
Pine isn’t the only Canadian startup trying to simplify mortgages, but they are carving out a strong position. Other players in the space include:
Perch – Helps Canadians plan, search, and apply for mortgages with tools that optimize based on their financial profile.
Nesto – Offers fully digital mortgage pre-approval and underwriting, with a focus on fast, low-rate offers.
Homewise – A brokerage that pairs users with personalized mortgage recommendations and handles lender negotiations.
Breezeful – Focuses on helping immigrants and first-time homebuyers access lending through a tech-enabled platform.
What sets Pine apart is how full-stack they’ve gone. They aren’t just matching you to lenders, they’re the lender themselves. That control over the experience, combined with their tech-driven workflow, allows them to compress timelines, improve transparency, and build something that feels genuinely modern. They're betting on a future where mortgages are as easy to manage as your favourite consumer app, and they’re pretty close to making it real.
Why this company and these roles stand out
The mortgage industry is massive, outdated, and notoriously frustrating. Pine is bringing a clear, clean solution to the table, and they’re doing it with both empathy and execution.
If you want to work at the intersection of real estate, fintech, and product-led growth, this is one of the most exciting Canadian startups to watch. They’re building for people who expect more from financial services, and they’re doing it really, really well.
🧭 Pine Roles — Now Hiring
Pine is hiring for a variety of roles, although not fully aligned with the ideals of LaunchPad but I still think they are worth checking out. As always, tune into our next LaunchPad post on Tuesday to see more featured jobs from Pine and other great tech companies in Toronto as soon as they are live 🚀
That’s a wrap on Spotlight #7
If you made it this far, thank you for reading. I hope these spotlights help you discover companies worth your time, and make the job hunt feel just a little bit less overwhelming. Keep an eye out for next Tuesday’s LaunchPad job drop, and if you know someone looking to break into tech or level up, feel free to share this with them too.
Here’s to building something cool, or better yet, joining something cool. 🚀
I just started as a BDR at Pine this week aha! Feel free to reach out with anything