What does it take to build and scale a vertical SaaS giant over two decades? According to Tooey Courtemanche, CEO and Founder of Procore, it’s about focus, perseverance, and a relentless commitment to customer success.
In a recent conversation with SaaStr CEO and Founder Jason Lemkin, Tooey shared insights into his 23-year journey as CEO of Procore, the leading SaaS platform for construction management. From surviving economic downturns to scaling into a multi-product enterprise serving millions, Procore’s story is a masterclass in vertical SaaS excellence.
5 Unexpected Learnings from Procore’s 23-Year Journey to $1B+ in ARR:
The Great Financial Crisis Was Actually a Massive Competitive Advantage. Most SaaS founders think economic downturns are purely negative, but for Procore, the 2008 crisis was an “extinction level event” that wiped out 20+ competitors. While painful (the founders went without salary for 2 years), emerging as one of the few survivors gave them an almost unbeatable market position. Sometimes survival = massive opportunity.
Industry Veterans Often Make Terrible Sales Hires. Surprisingly, Procore learned that hiring people directly from construction to do sales usually fails. Instead, they found success doing the opposite: hiring great salespeople and teaching them construction. The domain experts are brought in as sales engineers instead. A key insight for vertical SaaS companies trying to crack industry-specific sales.
Brand Building Has to Start from Zero in Every New Market. Even at $1.2B+ ARR. Procore discovered that their dominant U.S. brand meant nothing when entering new markets like the UK or UAE. There are no shortcuts – they have to rebuild their brand from scratch in each new region, even with huge resources behind them. A humbling lesson in global expansion.
The Multi-Product Journey Took Way Longer Than You’d Think. While multi-product is all the rage in SaaS today, Procore didn’t start seriously implementing their multi-product strategy until years 14-15. And this was intentional – they waited until customers specifically asked for new products. Today their average customer uses 3-4 products, but it was a 15-year journey to get there.
Enterprise Features Don’t Drive Out The Small Features Even at $1.2B+ ARR. and hundreds of millions in R&D spend, Procore still ships 3-4 “lighthouse features” in every release – just like they did as a small startup. They didn’t abandon small, focused improvements even while building massive enterprise functionality. A surprising insight into how to maintain product momentum at scale.
AI & The Future of Construction SaaS
The construction industry is infamous for being labor-constrained. With AI, Procore is poised to help its customers do more with fewer resources. “There just aren’t enough people who know how to build data centers, bridges, and skyscrapers,” Tooey explains. AI can help by automating repetitive tasks and improving decision-making through predictive analytics.
Procore isn’t looking to monetize AI separately—at least, not yet. “Our industry will unlock more budget for AI-driven insights once they see the impact on their bottom line.”
The company’s vision for the future centers on the strategic application of AI and automation. They’re focusing particularly on automating repetitive tasks through AI agents, freeing up human resources for more complex and valuable work. Their massive dataset, accumulated over years of industry leadership, provides a unique foundation for improving decision-making across all aspects of construction management. This data advantage could prove particularly valuable in mega-projects, where the potential to reduce errors through AI-driven insights could save millions of dollars and months of delays. The combination of their deep industry knowledge with cutting-edge AI capabilities positions Procore to potentially transform how construction projects are planned, executed, and managed in the coming years.
A SaaS Marathon
Tooey has been the founder and the helm of Procore for over two decades, a rare feat in an industry where leadership transitions are common. What’s kept him going? “When the thing that you do is part of who you are, it’s different,” he says. But balance is key: “When I get home, I’m not the CEO of Procore—I’m just Tooey.”
“ I will say this to all of the founders out there too, that as much as you want to be the face of the business, you don’t want to be the totality of the business. You can’t scale to a billion dollars in revenue without having an amazing team under you that is doing just that. Some founders conflate themselves as being the business and Procore has gotten so much bigger than me over the years that I’m just the I’m just the conductor.”
‘Duck Diving’ the Global Financial Crisis
Procore first started as a niche tool for high-net-worth residential builders in places like Aspen and Beverly Hills. “Our first customers were building homes for Eddie Murphy, Barbara Streisand, and Ben Stiller,” Tooey recalls. For Procore’s early customers, it was a combination of a homeowner who was on the road a lot and a distributed builder team. There was complexity around each home project as most of these homes were built like commercial buildings.
Procore quickly found early product-market fit by being narrowly focused and doubling down on its customer profile of custom home builders serving high-net-worth individuals. And with a pricing model of $195 per month, Procore was capital-efficient but not yet an established industry giant. Over its first decade, Procore grew and expanded from serving the construction project manager to serving multiple stakeholders, multiple products and multiple geos.
Then came the 2008 financial crisis. Almost overnight, residential construction came to a stop, forcing Procore to pivot toward commercial projects. “We lost nearly every customer,” Tooey admits. But the companies that survived the recession—mixed-use and commercial builders—became Procore’s new focus.
That pivot paid off. By 2016, Procore was a multi-product, multi-stakeholder platform expanding into enterprise and mixed-use construction firms.
Tooey explains: “Once everything came out of the great financial crisis, around 2011-12 in our industry, it was really interesting. I don’t know if you surf, but if you duck dive under a wave and on a surfboard and you go underwater, you come up the other side. I always think of that as the great financial crisis. Because when we duck dove that wave with 30 others, we were the only ones who came up the other side.
It was an extinction-level event, which gave us this huge advantage of buying us more time to capture the market share.”
The Multi-Product Journey: Patience and Precision
Procore’s multi-product evolution is a masterclass in timing and execution. While they started thinking about becoming a multi-product company around year five, they didn’t seriously implement this strategy until 2016-2017 – about 14-15 years after founding. This patient approach allowed them to build a strong foundation before expanding their product line.
The company’s multi-product strategy was firmly rooted in customer demand. Rather than rushing to build new products, Procore only developed solutions that customers explicitly requested. This disciplined approach was particularly effective in the construction industry, which was largely non-digitized and had obvious problems to solve. By letting customer needs drive their roadmap, they ensured each new product would find immediate market acceptance.
The transition from a single-product to a multi-product company proved to be one of Procore’s biggest challenges. It required careful resource allocation and strategic decision-making about where to invest their limited resources. The company had to maintain quality across all products while scaling, a balancing act that many companies struggle with. This transition was made easier by their patient approach and strong understanding of customer needs.
Today, integration across products has become a key differentiator for Procore. The average customer uses three to four products, while larger customers typically use five to six. This integration strategy has proven prescient as the era of point solutions has largely ended, with customers demanding comprehensive, integrated solutions rather than standalone products.
Perhaps most importantly, Procore’s multi-product approach has created a valuable data advantage. By collecting data across multiple products and workflows, they’ve built a comprehensive data corpus that enables better pattern recognition and insights. This has positioned them particularly well for the AI era, as they can leverage this data to provide increasingly sophisticated solutions to their customers.
Brute-Forcing Enterprise Adoption & Market Expansion
Moving upmarket wasn’t easy. Procore had to prove its value to large enterprises that had relied on pen and paper for decades. “We picked the Boston market, knocked on doors, and got one big name to trust us. That led to a FOMO effect, and soon, everyone wanted to meet with us,” Tooey explains.
That hyperlocal approach worked because Procore’s customers—project managers—moved between companies, bringing the software with them. “Our best salespeople have always been our customers,” he says.
Over the years, Procore also picked up on how to capitalize on what they call the triple TAM. Tooey explains, “if you think about it this way, an average commercial construction project probably has 30 different trade groups on it. And all of those folks are people that we sell to. We call it the triple TAM because one project, we can have three different cohorts of stakeholders that are customers which is really good for Procore because the nature of construction is very collaborative, and all teams. While all of these stakeholders work for different companies, they all share the same workflows. And so to be able to tie all that together and to de-risk it for everybody is really advantageous.”
The second secret that led to Procore’s success in going up-market was turning their best customers and users into in-house employees and resources. Field experience across sales engineering, and success – essentially doubling down on domain expertise has continued to help Procore thrive.
Today, the average Procore customer uses three to four products, with large enterprises using five to six. “The era of point solutions is over,” Tooey states. Customers expect an all-in-one platform and vertical SaaS founders must deliver from day one.
One challenge Procore faced in expansion was assuming brand awareness. “In the U.S., everyone in construction knows Procore. But when we enter a new country, we have to start from scratch.” The playbook shifts: heavy investment in domain experts to build the brand in a trusted way, and local market adaptation is key.
The Power of Domain Expertise in Vertical SaaS
Procore’s success hinges on their deep understanding of construction’s complexity. The construction industry presents unique challenges, operating on remarkably thin margins of just 2-3% while dealing with high liability and complex stakeholder relationships. These stakeholders include owners, general contractors, and subcontractors, all generating intensive data flows that need to be managed and coordinated effectively.
To address these challenges, Procore developed a multi-faceted approach that leverages deep domain expertise at every level of the organization. They made the strategic decision to hire industry experts as sales engineers, ensuring that their sales team could speak the language of construction and truly understand customer needs. They built specialized teams focused on different stakeholder groups, recognizing that owners, contractors, and subcontractors each have distinct needs and priorities. Perhaps most importantly, they created a platform robust enough to handle the complexity of construction projects at scale, something that could only be achieved through their thorough understanding of the industry’s nuances.
Final Takeaways
Tooey’s journey underscores key lessons for SaaS founders:
Customer obsession wins – Focus on solving real problems, not chasing market share.
Adapt or die – The best SaaS companies pivot when faced with existential threats.
Multi-product is the future – Customers want an ecosystem, not a single tool.
AI will redefine workflows – In industries with labor shortages, AI isn’t just useful—it’s essential.
For founders navigating the fast-moving SaaS landscape, Procore’s story is a testament to the power of long-term thinking and relentless execution. The industry is changing fast—but for Procore, that’s just another opportunity to build.
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