Richy Nelson

Who is Richy Nelson

Twelve years old. First roof. Still going up.

Richy Nelson got on his first roof when he was twelve. His grandfather had built a roofing business. His uncle had expanded it. His father had worked it. And Richy spent his summers on job sites, watching a trade that ran on handshakes, paper estimates, and hard-won relationships - all of it vulnerable to a single bad hire or a homeowner who got three wildly different quotes and picked the wrong one.

That childhood on rooftops didn't feel like a business thesis at the time. It felt like a summer job. But two decades later, it's the reason Richy Nelson is CEO of Roofr - a San Francisco-based SaaS company serving over 12,000 roofing contractors across North America, backed by TCV and the largest roofing supplier on the continent. He didn't find his market. He grew up in it.

The founding bet

He quit. He sold the house. He moved to San Francisco.

Richy didn't stumble into tech. He spent nearly twelve years working in his family's roofing business before moving into sales at one of the largest roofing contractors in Toronto. Inside that company, he had a front-row seat to everything broken about how the industry worked. Homeowners couldn't find reliable contractors. Contractors were drowning in paper. Nobody had tools designed for how roofing businesses actually ran - seasonal, local, relationship-driven, quote-heavy.

In 2016, he partnered with Kevin Redman as CTO and Zachary Melo, quit his job, sold his house, and put everything he had into a company called Roofr. Not a pivot. Not a side project. A bet-the-farm founding moment that most first-time founders read about but don't actually make.

The accelerator years

Rejected in Montreal. Accepted into Y Combinator. Same month.

Roofr's early path wasn't a straight line north. The team applied to FounderFuel in Montreal and got turned down. But the Toronto accelerator scene was more forgiving - the DMZ at Ryerson University accepted them and gave them something money couldn't: an investor liaison named Laith who made introductions that kept the company alive in its earliest months. Nelson credits that relationship directly. Before the DMZ, he couldn't get a meeting with a venture capitalist.

Then came Y Combinator. The Summer 2017 cohort. Nelson, Redman, and the team packed up and moved from Toronto to San Francisco. Three months of near-24/7 work, YC mentor scrutiny, and the slow realization that building software for roofers was genuinely category-defining. At Demo Day, Nelson stood on a stage in front of hundreds of investors and pitched a company whose DNA was laid in a Toronto family trade. Crosslink Capital led the $4M seed round that followed.

Early proof came fast. In Roofr's first four weeks operating in California, one contractor - Geo - increased his sales by $160,000. That wasn't a case study. That was a signal about what happens when a trade professional gets real tools for the first time.

From marketplace to platform

Roofr started as a marketplace. It became an operating system.

Roofr's original model connected homeowners to vetted contractors - a consumer-facing marketplace with free estimates powered by satellite imagery. It worked. Homeowners saved an average of $1,500. Contractors got qualified leads. The company hit $200,000 in gross merchandising volume and 50% month-over-month growth in early phases.

But Nelson kept watching what happened after the lead. The contractor would get a job, then switch to spreadsheets, then a separate tool for proposals, then another for invoicing, then call a supplier manually to get pricing. The workflow was fragmented by design - or rather, by the absence of design. Nobody had built a single platform for how a roofing business actually operates from first contact to final payment.

Roofr became that platform. Satellite roof measurements. Digital proposals. Instant estimator. CRM. Invoicing. Payment processing. Supplier integration for real-time material pricing. The company launched its CRM in 2023, knitting together every tool a roofing contractor needs into one system. By 2025, over 12,000 roofing companies relied on Roofr - and many of them were generating millions in revenue through it.

Series B and what comes next

TCV didn't find Roofr. Roofr wasn't looking.

In January 2025, Roofr announced a Series B led by TCV - a firm whose portfolio includes names like Netflix, Spotify, and Airbnb. ABC Supply, the largest roofing materials distributor in North America, joined as a strategic investor for the second time. The deal confirmed what the numbers were already saying: Roofr is becoming the default infrastructure for the roofing industry.

Nelson's response to closing the round was characteristically unromantic. He wasn't in active fundraising mode. He took the capital because the timing and the partners were right - and because pulling back when others are building is the kind of move that costs market position. The roadmap for the new capital: canvassing tools, marketing automation, document builder, job costing, work orders, and deeper supplier integrations. The vision is a roofing business that runs entirely inside Roofr from first knock on the door to final payment.

Leadership & company values

Positive discontent as a company value.

Roofr's six core values aren't the usual corporate wallpaper. Unconventional thinking. Positive discontent. Collaboration. High performance. Customer obsession. Resiliency. The phrase "positive discontent" is particularly Nelson - it names the instinct to keep improving even when things are going well, the refusal to settle for the current version of the product when a better one is possible.

The company operates fully remote, with 150+ employees spread across North America. Nelson is known to personally reach out to customers - Roofr's Facebook page noted that he "loves chatting with customers" and that contractors shouldn't be surprised if they hear directly from him. In a company serving 12,000+ businesses, that's either extremely difficult to sustain or evidence of a culture that genuinely puts the customer at the center.

He also gives back to the ecosystem that helped him. Nelson serves as Alumni-in-Residence at the DMZ - the Toronto accelerator that first gave him access to investors before Y Combinator changed the company's trajectory. He's now the person making introductions for the next generation of founders in the same position he was in 2016.

What makes Richy Nelson tick

Career Timeline

From first roof to Series B.