Tooey Courtemanche on Procore's Long Road to Growth and the Work of Leading

Procore founder and CEO Tooey Courtemanche says entering a market requires patience. When he started the construction software company in 2002, internet access and mobile devices were not yet common on building sites. He believed the industry would eventually digitize, but the company had to survive until it did.

Courtemanche traces Procore's origin to a move from the Bay Area to Santa Barbara. His wife Hillary wanted the family together rather than waiting for him to return from frequent business travel. While they built a house, she grew tired of hearing about construction problems and suggested he solve them himself.

He began working alone in a guest room. When Hillary repeatedly interrupted a customer call because she needed an ingredient from the store, he decided to rent an office. He credits her with pushing both the original idea and the move into a dedicated workspace.

Before the global financial crisis, Procore sold mainly to custom home builders. When that market collapsed, the company shifted toward commercial construction. The transition took roughly two years; Courtemanche and co-founder Steve Zahm went without pay, sold assets and borrowed from friends and family to get by.

Courtemanche says he remained convinced construction would digitize and that Procore's approach could work if given enough time. Asked when a founder should stop, he says founders may sense when an idea truly will not work, although Procore itself struggled for years. This is his personal judgment, not a reliable test for every venture.

He says he struggled in school, left college and worked as a carpenter. He wanted to overcome other people's low expectations and his own. In hindsight he suspects he has dyslexia, but presents that as his belief, not a diagnosis; he says he learns intensely when a subject engages him.

Courtemanche says his love of the mission helped him endure the long difficult period. He wants to connect people across the construction industry on a global platform, while recognizing that a founder's imagined final state of perfection may never arrive.

Procore's early growth was constrained by market readiness: it sold cloud software to an industry without internet on many job sites. Courtemanche and Zahm even traveled to a customer, bought networking equipment and installed access so the customer could use a $95-a-month service.

He says an early investor would have needed several things to go right: construction digitization, workers' ability to use the tools, job-site connectivity, mobile devices and recognition that software could improve productivity. Each dependency added risk, even though a successful outcome could be valuable.

Courtemanche recalls many competitors disappearing after the financial crisis, while an investor helped Procore survive. He dates the adoption inflection to around 2015: the company had grown from zero to $9.6 million in revenue over 13 years, then growth accelerated. These are his retrospective figures.

A memorable signal came when Zahm no longer needed to check the mailbox daily for customer payments to cover payroll. The founders believed they had enough product-market fit to raise capital and accelerate. Courtemanche attributes the change primarily to the market catching up, rather than a sudden new product.

The company had not simply waited through the lean years. It accepted custom software work unrelated to Procore when the revenue could keep the lights on. Courtemanche advises founders in a cash crunch to find revenue and preserve the ability to continue, while acknowledging that such side work was not necessarily ideal.

Zahm's business background complemented Courtemanche's product and customer focus. When they considered institutional capital, Zahm argued the company had reached sufficient traction. Courtemanche was interested but intimidated by meetings with established venture investors.

An earlier 2008 fundraising trip had gone badly. Courtemanche recalls an investor saying the idea would be more attractive if it were more like Facebook, and others questioning software for an industry that could not yet use it. Years later, when the market changed, he found some people treated the same founders as unusually insightful.

When they returned to raise money, Courtemanche focused on the individual partner rather than the firm's brand. He spent time getting to know Brian Feinstein and Will Griffith, looking for shared values and investors committed to the mission. He says both remained on Procore's board at the time of the interview.

He recalls raising approximately $30 million in the first institutional round and says Bessemer's internal upside scenario had valued Procore at around $300 million. He later learned more about that assessment from Paul Landers, who had worked on the investment and joined Procore as CFO. The numbers are his recollection.

Courtemanche says relationships can make fundraising emotionally difficult. He recalls investors he did not choose trying to make him feel guilty, and wishes he had run a more structured process. He praises his eventual investors for being straightforward; those investors' continuing board relationship is relevant to his account.

After the financing, he says revenue doubled repeatedly and the business was moving rapidly by around 2017. He compares the period to jumping off a skateboard going downhill: the team was running hard to avoid falling, with little time to reflect. A later private valuation of $1 billion surprised the leadership team.

Courtemanche thinks some naivety helped the founders stay focused on solving a customer problem instead of obsessing over every obstacle. Stebbings then asks how Procore expanded its product line without losing focus.

Until 2017, Procore had one main project-management product. Customers wanted fewer disconnected point solutions, so the company ranked their needs and expanded toward areas such as finance, quality and safety. Courtemanche emphasizes prioritizing the biggest needs rather than building everything at once.

One newer financial product grew quickly but was not ready for enterprise scale. Around 2019, Procore paused new feature development for a year to re-architect it. Courtemanche says it was hard to tell customers to wait, but that the subsequent feedback validated the decision; the established project-management product was a separate, more mature offering.

He recalls demand from Australian and New Zealand customers for quality and safety software, driven in part by concerns about local safety obligations. Procore built for that need and found customers elsewhere also valued the product. His account of the legal context is a business recollection, not legal advice.

International expansion taught Courtemanche that a US playbook does not automatically transfer. He recommends first building local brand recognition and referenceable customers, then scaling sales. In hindsight, Procore entered some early markets too aggressively and learned that building trust takes time.

Because customers could already buy internet software remotely, he suggests deploying customer-success and field or product-marketing people first, followed by a go-to-market team. He estimates that Procore's core product fit many new construction markets reasonably well, while still requiring local work.

Procore chose construction volume rather than per-seat pricing. Courtemanche wanted everyone on a project, including subcontractors, to be able to collaborate without a seat-by-seat decision. A customer explained that construction insurance was purchased against project volume, giving him a familiar measure that could scale with the customer's business.

He says the pricing model was initially unpopular and some customers still dislike it. But customers could involve their collaborators, and subcontractors using the platform could introduce it to other contractors. Courtemanche sees the model as supporting the network the company was trying to build.

Although he speaks with customers almost every day, Courtemanche says he stopped negotiating commercial terms five or six years before the interview. He wants his relationship with customers to support a long-term strategy rather than become transactional. In his view, direct customer contact remains central to the CEO role.

As a company grows, founders have to shift from doing everything themselves to enabling others. Courtemanche says this is especially difficult for newly promoted managers accustomed to solving each problem personally. Delegation requires allowing people to learn through mistakes while limiting the possible damage.

He has become more comfortable delegating by identifying his weaknesses and hiring people whose strengths complement them. He focuses on vision, priorities, resources and customer needs, while relying on skilled finance, legal, people and operations leaders. He doubts that becoming merely adequate at every weakness would serve Procore at its scale.

The public image of a CEO can hide the job's complexity. Courtemanche describes the role as constant and says responsibility grows as the company grows: at the time, he cited roughly 4,000 employees and more than 16,000 customers. Stebbings notes that financial security also makes life easier; Courtemanche agrees, while saying the stress has changed rather than disappeared.

Procore deliberately hires for its values, he says, once candidates have shown the skills for the role. His shorthand is 'hungry, humble, smart.' He recalls hiring highly capable but insufficiently humble people and regretting the effect on collaboration and culture; this is his assessment of those experiences.

Courtemanche says employees seeking promotion should demonstrate the broader work before receiving the title, while supporting their manager rather than neglecting their current responsibilities. He prefers people who bring potential solutions to problems, not just a list of problems.

He credits Shopify's Tobi Lütke with advice that leadership skills must grow as fast as, or faster than, the company. When a loyal employee is not keeping pace, he tries coaching and, where possible, finding a role in which they can succeed. If that fails, he says the company should part ways empathetically and help with the next move.

Courtemanche remembers feeling out of place at investor conferences as a college dropout and carpenter among CEOs with more conventional credentials. After a difficult period of trying to resemble others, Hillary told him to be himself. He says choosing authenticity and vulnerability brought relief and a supportive response.

On difficult days, he calls a customer to reconnect with the work he loves. He also considers capital allocation one of the CEO's central responsibilities. His preference is to make decisions quickly when the potential downside is contained, learn from the results and avoid allowing indecision to become the default.

Asked about money, Courtemanche says he thinks more about pursuing a mission than becoming an entrepreneur for its own sake, while recognizing that not having to worry about money is a privilege. He also says success can reduce the amount of candid feedback a leader receives.

He relies on a small personal 'cabinet'—including Hillary and former CFO Paul—to challenge his ideas and keep him grounded. Without people willing to disagree, he worries that a leader's weakest ideas can be treated as brilliant and acted on.

Courtemanche says he and Hillary tried to raise their son Henry with responsibility and freedom inside clear boundaries rather than pretend the family's circumstances were different. He is proud of the adult Henry has become. He describes their approach as a personal experience, not a general parenting rule.

His biggest regret, he says, is missing stretches of Henry's life while consumed by Procore. He describes recently turning down an invitation to a football game because of an earnings week. Stebbings challenges the choice, and Courtemanche acknowledges he might have made a different decision while explaining his need for rest before a demanding week.

When overwhelmed, Courtemanche needs time alone. He builds intricate Lego sets because they demand focus and give him a break from thinking about Procore. He also says his wife makes space for him and maintains a boundary between the company and their family life.

He cautions that he has not figured out universal rules for marriage. What works for him and Hillary includes giving each other room for separate interests and returning attention to family when he comes home. He compares marriage and company building as continuing work rather than a destination where every problem disappears.

Asked whether younger people are too delicate, Courtemanche hesitates to generalize and questions whether he risks sounding like an older person criticizing the next generation. He nevertheless believes adversity can develop resilience, and offers his opinion about economic cycles and changing expectations of work.

In quick-fire questions, Courtemanche credits persistence and luck for success. A family friend once knocked on his door after he had left construction and offered to mentor him in technology; he sees accepting that offer as a pivotal chance event.

He recalls disagreements with Zahm over spending, including $100 on branded hats when Procore had little money. Courtemanche wanted to build and spend; Zahm protected scarce resources. In hindsight, Courtemanche says the financial discipline helped keep the company alive.

If he could lead another company for a day, he would choose Microsoft, intrigued by the complexity that mentor Satya Nadella manages. On competition, he prefers to focus on customers and the finish line rather than constantly looking at rivals.

Courtemanche wishes he could speak with his late grandfather, a bank CEO who took his company public and treated people with dignity regardless of their position. He says his father, who saw him struggle at school and work in construction, remains surprised by his later success.

A professor once advised him to use five spare minutes to complete a five-minute task. Courtemanche says that lesson shaped his productivity. He never expected Procore's eventual scale, but believed that, if the venture failed, he could return to carpentry and earn a living.

His indulgences reflect his love of construction: he bought a bulldozer for his ranch and enjoys building roads. He describes driving an old pickup and recently buying a watch, framing those choices as personal preferences rather than a performance for others.

Looking ten years ahead, Courtemanche imagines possibly preparing for retirement and spending time building at his ranch. He describes projects including a barn, deck and a small western-style town, and expects to keep working with his hands.