Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090
Tooey Courtemanche Jr. (guest), Harry Stebbings (host)
In this episode of The Twenty Minute VC, featuring Tooey Courtemanche Jr. and Harry Stebbings, Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 explores from Dyslexic Carpenter To Procore’s Patient, Billionaire SaaS Visionary CEO Tooey Courtemanche, founder and CEO of Procore, recounts his 21-year journey digitizing the construction industry, beginning as a struggling carpenter and college dropout and evolving into a public company leader.
From Dyslexic Carpenter To Procore’s Patient, Billionaire SaaS Visionary CEO
Tooey Courtemanche, founder and CEO of Procore, recounts his 21-year journey digitizing the construction industry, beginning as a struggling carpenter and college dropout and evolving into a public company leader.
He explains how extreme market-timing risk, a 13‑year slog to real product‑market fit, and nearly going bust during the GFC forged Procore’s persistence, discipline, and customer-centric culture.
The conversation dives into lessons on fundraising, pricing strategy, product line expansion, international growth, leadership evolution, and capital allocation.
Courtemanche also reflects on identity, imposter syndrome, marriage, parenting, and how to stay grounded while building a multi‑billion‑dollar business.
Key Takeaways
Persistence over years can trump perfect timing—if you can survive.
Procore grew from $0 to only $9. ...
Get the full analysis with uListen AI
Founders must distinguish between doing and leading—and be willing to let others fail safely.
Courtemanche emphasizes that early-stage founders do everything, but at scale the job is to empower and coach; this requires deliberately delegating, tolerating small failures (with limited blast radius), and resisting the urge to jump back in.
Get the full analysis with uListen AI
Hire and promote on values and behavior, not just pedigree or performance spikes.
Procore screens hard for “hungry, humble, smart” and has repeatedly regretted hiring brilliant but non‑humble “luminaries” who damaged culture; once culture is strong, the organization itself ejects people who don’t fit.
Get the full analysis with uListen AI
In new geographies, build brand and reference customers before you build a sales machine.
Their international playbook now starts with customer success, field, and product marketing to create local advocates and trust, only later layering in heavy go‑to‑market investment, rather than assuming the U. ...
Get the full analysis with uListen AI
Pricing should align with how value is created and how work actually happens.
Despite customer resistance, Procore chose a volume‑based model (construction volume) instead of per-seat, because construction is a team sport and seat-based pricing would limit collaboration and undermine their mission to connect everyone on a project.
Get the full analysis with uListen AI
Capital allocation is a core CEO skill—sometimes you must halt visible progress to fix foundations.
Courtemanche describes pausing new features on a fast-growing financials product for a full year to re‑architect it for enterprise scale; customers initially resisted but later praised the decision, illustrating disciplined, long-term capital allocation.
Get the full analysis with uListen AI
Authenticity beats cosplay leadership; trying to fit the stereotype breeds misery.
Struggling with imposter syndrome among elite, Patagonia-vest SaaS CEOs, Courtemanche’s turning point was his wife urging him to stop pretending; once he leaned into his authentic carpenter‑founder identity, people responded more positively and he led better.
Get the full analysis with uListen AI
Notable Quotes
“The way you enter markets matters, and you have to be patient. Nothing's gonna happen overnight.”
— Tooey Courtemanche
“Founders are usually cut from a different cloth. I'm a dog on a bone—no one was ever gonna take this vision away from me.”
— Tooey Courtemanche
“Between 2002 and 2015 we grew from $0 to $9.6 million. From 2015 on, it started to accelerate.”
— Tooey Courtemanche
“If you walked onto any construction site in 2002, there was no internet at the job site—yet I’d built a SaaS solution for them.”
— Tooey Courtemanche
“In the early days you do everything. At a certain point you have to learn how to stop doing and start leading.”
— Tooey Courtemanche
Questions Answered in This Episode
How do you know if your belief in a market is justified persistence versus delusional stubbornness when traction is slow for years?
Tooey Courtemanche, founder and CEO of Procore, recounts his 21-year journey digitizing the construction industry, beginning as a struggling carpenter and college dropout and evolving into a public company leader.
Get the full analysis with uListen AI
If you’re pre–product-market fit in a timing‑risk market, what concrete steps can you take to generate survival revenue without derailing the core vision?
He explains how extreme market-timing risk, a 13‑year slog to real product‑market fit, and nearly going bust during the GFC forged Procore’s persistence, discipline, and customer-centric culture.
Get the full analysis with uListen AI
How would Procore’s growth and adoption have differed if they had chosen a standard per-seat SaaS model instead of construction-volume pricing?
The conversation dives into lessons on fundraising, pricing strategy, product line expansion, international growth, leadership evolution, and capital allocation.
Get the full analysis with uListen AI
What specific signals should a founder watch for to know it’s time to shift from being the main doer to being primarily a leader and capital allocator?
Courtemanche also reflects on identity, imposter syndrome, marriage, parenting, and how to stay grounded while building a multi‑billion‑dollar business.
Get the full analysis with uListen AI
In international expansion, how can a smaller company without Procore’s resources practically build brand and reference customers before deploying a full sales force?
Get the full analysis with uListen AI
Transcript Preview
(instrumental music plays) The way you enter markets matter, and you have to be patient. Nothing's gonna happen overnight. You know, if you were to invest in Procore in 2002, the internet was not at the job site. There was no such thing as mobile technology at all. We just were super early. I knew it was gonna happen. I'd seen all these other industries digitize, and I'm like, "It's just a matter of time." We just have to be patient.
What have been the biggest lessons from international expansion?
You know, it's really tempting to say what worked in the US market is gonna work in another market. I would say some of the biggest lessons learned was...
Tuy, I am so excited for this. You very kindly said you listened to the show before. I've been a fan of the Procore business from afar for a while, so I'm very excited, and thank you for joining me.
I think I'm equally as excited, Harry. This is- I'm a huge fan of what you do, and so this is, uh, quite an honor to get to join you today.
Oh, that's not at all, but Procore has been an epic 21-year journey, and I heard from a little birdie that actually this is, uh, down to your wife, Hillary, who came up with the idea wanting to move to Santa Barbara, but that was all I got. So how did Hillary, Santa Barbara move lead to Procore?
So yeah, so I was- I was running a small tech company up in the Bay Area, in the heart of Silicon Valley. And by the way, I was flying all over the United States, uh, servicing clients in a completely different industry. And my wife said to me one day, "Hey, guess what? We're moving to Santa Barbara." And I'm- and I said, "No we're not. You- we live in the Bay Area and I run a business up here." She goes, "No, your son and I are moving to Santa Barbara. We haven't seen you in months 'cause you- all you do is travel, and if you're not, we're not gonna see you. We'd rather not see you in Santa Barbara than San Francisco." And so I, uh, vi- just very much against my best judgment, I'm- I came down here kind of kicking and screaming and, uh, and lo and behold, you know, we started building a house, and, you know, she got sick of me complaining about the challenges with building the house. And so she said to me, like, "Hey, why don't you just go out and solve this problem and stop complaining about it?" And that was the, uh, origin story of Procore. So, uh, yeah, sh- it's all her, it's all her idea.
Uh, tell me, have you given her due credit along the way, Tuy?
No, I- I take all the credit. (laughs) No, I'm just kidding.
Install uListen to search the full transcript and get AI-powered insights
Get Full TranscriptGet more from every podcast
AI summaries, searchable transcripts, and fact-checking. Free forever.
Add to Chrome