The Twenty Minute VCTooey Courtemanche: From Construction Worker to Billionaire CEO | E1090
At a glance
WHAT IT’S REALLY ABOUT
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.
IDEAS WORTH REMEMBERING
5 ideasPersistence over years can trump perfect timing—if you can survive.
Procore grew from $0 to only $9.6M in revenue in its first 13 years while the market and infrastructure caught up, then inflected after 2015; the only reason it worked was relentless persistence plus enough cash and scrappy side-revenue to stay alive.
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.
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.
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.S. model ports instantly.
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.
WORDS WORTH SAVING
5 quotesThe 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
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