Feb 14, 2025 · 42m · saastr
Going Long: How Procore’s Founder Tooey Courtemanche Built a Billon-Dollar SaaS Empire Over 23 Years
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this SaaStr interview, Procore founder and CEO Tooey Courtemanche reflects on his 23-year journey scaling a vertical SaaS empire, navigating economic downturns, expanding into enterprise markets, and integrating AI to transform the global construction industry.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 32.9% of the talking time here. How this is scored →
Jason as informed peer 6.0 Guest teaching 5.1 Guest disagreement 1.3 Jason pushing back 2.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 22:18 Rejection of big tech sales aggression
Tooey forcefully rejects the idea that aggressive enterprise reps can bulldoze construction prospects, recounting how buyers kick arrogant sellers out of their offices.
Hardest push from Jason ▶ 21:03 Questioning generalist sales rep valueJason pushes back on whether standard B2B sales reps provide any real value in complex vertical sales conversations without deep domain knowledge.
Biggest teaching moment ▶ 16:00 Debunking construction industry stereotypesTooey corrects conventional misconceptions about construction, explaining that it is a highly sophisticated, data-intensive, low-margin industry rather than simple manual labor.
Jason holds their own ▶ 26:20 Comparing vertical TAM strategies to KlaviyoJason demonstrates SaaS expertise by contrasting market concentration in ecosystem verticals like Klaviyo on Shopify against Procore's multi-trillion global construction TAM.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Procore's Early Architecture and Capital Efficient Foundations | 5 | 5 | 1 | 2 | Jason probes Procore's early unit economics and customer profile, comparing early SaaS pricing models. Tooey details how serving custom home builders with absentee high-net-worth owners laid the foundation for project management workflows across all construction verticals. | |
| Navigating the 2008 Financial Crisis and Near-Death Survival | 6 | 4 | 1 | 1 | Jason compares his own 2008 experience at EchoSign with Procore's near-total market wipeout in residential construction. Tooey shares how pivoting to mixed-use commercial projects and surviving with an angel bridge loan eliminated their competitive field. | |
| Breaking into Enterprise and Leveraging Construction Word-of-Mouth | 6 | 5 | 1 | 2 | Jason asks about customer retention pressures versus word-of-mouth expansion in modern SaaS. Tooey explains the hyper-local nature of construction and how transient project managers naturally champion the platform across firms. | |
| Managing Multi-Stakeholder Workflows and Sales Enablement | 6 | 6 | 2 | 3 | Jason questions whether sales reps need deep domain expertise or if generalist B2B reps suffice. Tooey clarifies that generalist reps fail without structured enablement and pairing with former field project managers acting as sales engineers. | |
| Multi-Trillion TAM, Disciplined Capital Allocation, and Coding | 7 | 5 | 2 | 2 | Jason contrasts Procore's multi-trillion TAM dynamics with Klaviyo's 80% market share in Shopify. Tooey reframes the goal from obsessing over market share percentages to solving customer problems and managing capital allocation across massive R&D budgets. | |
| Transitioning from Point Solutions to an Integrated Data Platform | 6 | 5 | 1 | 2 | Jason notes that modern vertical SaaS companies go multi-product far earlier than Procore did. Tooey agrees that the era of point solutions is over because construction requires a unified data corpus rather than fragmented siloed apps. | |
| Artificial Intelligence, Labor Shortages, and Value-Driven Pricing | 6 | 6 | 1 | 2 | Jason asks whether AI features justify additional monetization or should be bundled to drive 10x customer value. Tooey outlines severe industry labor shortages and explains how autonomous agents and reasoning models eliminate costly construction mistakes. |
Statements from this episode (15)
Lemkin: 90% of SaaS companies that IPO have a founder CEO
“I did this analysis a little while ago that of the SaaS companies that IPO, 90% of a founder CEO.”
Courtemanche: Procore initially priced its software at $95 and $195 monthly
“We had two versions of our product. We had a full version for 195 dollars a month and a truncated version for 95 dollars a month.”
Courtemanche: Procore raised only $5M across its first nine years
“I think in the first Nine years of Procore's existence, we raised five million dollars, right?”
Courtemanche: Construction managers face identical problems at every scale
“If you're a project manager on a Eddie Murphy's house or A nuclear power plant or a Whatever, a waste treatment plant or a wind farm. You basically are dealing with the same set of problems. They just are different scales and they might have different terminol…”
Courtemanche: 2008 crisis wiped out Procore's custom home builder customer base
“By the way, during the great financial crisis, which is when everything changed to Procore, was all of our custom home builders went out of business. Like literally every customer we had, and the world stopped for eight months.”
Courtemanche: Procore was the sole survivor among 30 construction competitors
“Cause when we duck dove that way with 30 other surfers, we're the only ones who came up the other side. Everybody did. ... Yeah, it was an extinction level event, which gave us this huge advantage too, of buying us more time to capture the market share.”
Courtemanche: A $300k check from DoubleClick founder Kevin O'Connor saved Procore
“And so he basically wrote us a check for like, 300,000 bucks and basically to keep us alive. And that check alone saved Procore. In fact, he's been on our board for 20 years.”
Courtemanche: Procore's main competition has always been pen, paper, and Office
“The incumbent software for our entire history, whenever we go into an account has always been pen and paper or really Microsoft office.”
Courtemanche: Vertical SaaS Companies Only Get One Chance on Brand Impression
“And the vertical market like Procore is you have one chance to make a good impression with your brand. And if you make a bad impression, you're essentially doomed in that market.”
Courtemanche: Hire Trained Salespeople and Teach Them Domain, Not Vice Versa
“So there's a lot of nuances to all of this, but we do find you got to hire sales people that understand sales and teach them construction.”
Lemkin: Don't hire engineering leaders unless their bio leads with 'hacker'
“And what I learned for him is don't hire anyone where the first line in their bio, whatever, wherever it is, isn't hacker.”
Lemkin: Modern Vertical SaaS Startups Go Multi-Product by $10M ARR
“The vertical SaaS companies that I'm closest with, whether it's in restaurants or salon software, others, they're all multi-product by ten million or earlier.”
Courtemanche: Customers handle 50% more construction volume using Procore
“Our customers tell us that they can run 50% more construction volume on through their business if they're running on the Procore platform than if they're not.”
Courtemanche: Construction is a 2% to 3% gross margin business
“In the construction industry, it's a very low margin business, like two to three percent gross margin business.”
Courtemanche: Procore will not separately monetize AI for now
“For now, we're not looking to create a product line around this. That's going to be separately monetized. Now that's always open for debate. We really want to get more feedback from our customers before we make any sort of decision on that.”