Tooey Courtemanche and the business of being early

Before there could be a software subscription, someone had to install the internet. In Procore’s early years, Craig “Tooey” Courtemanche and Steve Zahm went to construction sites with Wi-Fi access points and routers. The service they were making possible cost $95 a month. There is something wonderfully unglamorous about this beginning: a cloud-software founder attending to the small matter of getting his customers into the cloud.

Courtemanche had founded Procore in 2002. Construction teams needed to coordinate drawings, decisions and people, and he believed a shared online platform could help. The difficulty was that his idea arrived before the necessary equipment had become ordinary on a building site. Being early is flattering in retrospect. At the time, it can look remarkably like standing outside a locked door.

Today he is Procore’s founder and chairman of the board. Ajei Gopal took over as CEO on November 10, 2025. The change gives this unusually long founding story a useful vantage point. Courtemanche spent more than twenty-three years as chief executive, enough time for his original customers’ working tools to change around him. He stayed attached to the problem while the means of solving it changed.

Sawdust before software

His first workplace was a cabinetry shop. In eighth grade, he swept up sawdust; his father was a builder. He later worked as a carpenter and tried real estate development. “I am a builder at heart,” he has said. For him, the word covers both the physical craft and the less tangible work of writing software or assembling a company.

That early apprenticeship matters because construction was familiar territory. He had worked in it before he became an executive trying to sell technology to it. His affection for the trades runs through the way he talks about the business. The people doing the building appear as capable professionals with difficult coordination problems, rather than as characters waiting for a visiting programmer to explain the future.

The move into software came during the Silicon Valley boom of the 1990s. From 1993 to 1996, he worked as a software engineer at Skip Stevely & Associates. From 1996 to 2001, he ran Webcage, the software consulting company he founded. It helped large companies move from analog call centers toward web-based self-service. He had seen businesses change their working habits when information became easier to reach.

Even his nickname has a workaday origin. He shares his first name with his father: “Craig, too” became Tooey. The result is an unusually informal name on a public-company board roster. It suits a career that began with a broom better than any carefully devised corporate persona could.

A house with too many messages

Procore grew out of building his own home in Santa Barbara. Courtemanche had already worked in construction and software, but the project brought those experiences together. The communication still depended on fax, phone and paper. Here was an industry producing complicated physical things while relying on scattered information to keep the work moving.

His wife, Hilary, belongs in the origin story. In his telling, she wanted the family to move from the Bay Area to Santa Barbara because his work kept him traveling. Once they were building the house, she tired of hearing him complain about the process and suggested that he solve the problem. He gives her the credit for the idea. Domestic exasperation has rarely received such an elaborate software response.

The name Procore also came from a practical ambition. Courtemanche wanted the technology to let people concentrate on their professional core competencies: their craft. The premise was that a builder should spend less time chasing information and more time building. A house creates a particularly good test of that premise. The information may be intangible, but the consequences of a misunderstood instruction are quite solid.

His earlier software work supplied the technical approach. A shared service could connect people without requiring every customer to maintain a separate server. In 2020, he described Procore’s beginning in five words: “born in the cloud in 2002.” The architecture was ready. Getting that architecture into the hands of people working outside an office would take longer.

“I am a builder at heart.”

Tooey Courtemanche

The future needed a router

Courtemanche bristles at the familiar description of construction workers as slow to adopt technology. He remembers entering job-site trailers where people were doing sophisticated work in Excel. They were already using the tools they could get. Their capacity to handle complexity was visible on the screen; the missing piece was useful connectivity and software suited to their circumstances.

This distinction changes the story. A reluctant customer and an unequipped customer present different problems. Courtemanche’s early visits with networking hardware are a literal illustration of the second. A product can be available for purchase while remaining awkward to use where the work happens. In construction, that distance between an office and a site was consequential.

As smartphones and tablets became commonplace, the distance narrowed. The people handling construction information could carry access to it. Procore’s opportunity became easier to act on. Courtemanche’s patience had a technological condition attached to it: the industry needed a workable route to the service. The eventual arrival of that route makes the early years look obvious, which is an easy mistake to make after the cables are connected.

When the customers disappeared

The 2008 financial crisis brought a more immediate problem. Procore had been selling largely to custom home builders. That market faltered, and the company shifted toward commercial construction. Courtemanche and Zahm went without pay for about two years while making the change. Courtemanche has described taking two mortgages on his house and selling his car to help keep payroll going.

The circumstances give the story a scale that a revenue chart cannot supply. A founder’s confidence has different consequences when a company’s survival reaches into the family finances. Hilary supported the decision to keep going. Friends and family helped them get by. The company survived through a combination of conviction, personal sacrifice and a change in the customers it served.

That last part deserves attention. His dedication to construction did not require him to keep selling to precisely the same builders. Commercial work became the route forward. The commitment was broad enough to accommodate a practical change. It is a less tidy story than the version in which someone simply believes hard enough and is eventually rewarded.

A handshake, then a larger company

In 2014, Bessemer partner Brian Feinstein met Courtemanche. Procore was already more than a decade old. Feinstein saw a founder whose enthusiasm for construction matched Bessemer’s interest in software built for particular industries. The firm led Procore’s first institutional investment round. Earlier supporters included Kevin O’Connor, who had backed the company personally.

Capital gave the team room to build a more systematic sales organization. It also brought connections to other software businesses whose experience could help. The company’s growth now involved learning how to sell and support the product at scale, alongside the engineering that had started it. Courtemanche’s own background had crossed trades; the organization was learning to cross disciplines.

The photograph from that year is a pleasing antidote to the solemnity of funding announcements. Four people link hands in front of a screen, Courtemanche on the right. A financial transaction has become a slightly awkward group exercise. For a company built around collaboration, the picture is almost excessively literal.

He also sent engineers into job-site trailers to understand the people using their work. That habit ties the larger business back to its beginning. The initial insight came from encountering an everyday construction problem. Returning to the site gave the product team a way to encounter more of them, without depending entirely on the founder’s memory.

The bell was nineteen years away

Procore began trading on the New York Stock Exchange on May 20, 2021, under the symbol PCOR. Its offering was priced at $67 a share. The distance from 2002 is nineteen years. It is a striking interval in a business culture that often compresses company histories into a brisk sequence of funding rounds and a celebratory photograph.

The exchange photograph does deliver the celebration: raised hands, smiles, a large bell. Courtemanche described the occasion as a gathering for the construction industry, with employees, customers and partners present. His company had reached a public market; the people whose work gave the software its purpose were part of the occasion.

Going public also brought quarterly earnings calls and additional regulatory obligations. Courtemanche said the global recognition of a stock-exchange listing helped conversations with prospective customers. The company had gained another credential. The work of explaining how its tools could help a particular project still remained.

A customer at the other end of the line

For all the scale, one of Courtemanche’s more revealing habits is small. When a difficult day piles up, he calls a customer. Speaking to someone using the product restores his enthusiasm for the work. There is no elaborate ritual involved. A conversation puts the company’s purpose back within earshot.

His public advice also makes room for uncertainty. He favors asking questions over pressing a position, and urges founders to examine their strengths and weaknesses honestly. Receiving UC Santa Barbara’s 2020 Venky entrepreneurial leadership award was particularly meaningful to someone who had left college without graduating. The honor recognized his contribution to the region’s technology community.

As Procore expanded its product range, customer requests remained a guide. Courtemanche has described the move into multiple products as a long process, with serious implementation arriving around 2016 and 2017. He also learned that recognition in the United States did not automatically produce recognition in another country. Each market required the team to earn familiarity again.

These are useful admissions from a founder whose company had acquired considerable size. A larger organization still has to listen, choose where to invest and introduce itself. His account leaves room for the ordinary labor hidden beneath the word growth. New markets contain actual people who have perfectly good reasons to ask what a company can do for them.

Keeping the problem, handing over the job

Courtemanche announced a CEO succession process in March 2025. In September, he introduced Gopal, previously chief executive of engineering-simulation company Ansys. He emphasized Gopal’s experience connecting the digital and physical worlds, along with his character and commitment to customers. The handoff took effect in November, when Courtemanche stepped away from operational responsibilities to focus on the board.

A founder who has worked on the same business since 2002 is handing over more than a calendar full of meetings. Procore contains years of decisions, relationships and habits. Courtemanche’s stated ambition as chair is to keep championing its mission and support the incoming leader. The title changes his responsibilities while preserving a connection to the work that started at his own house.

On his personal website, the future goal remains plain: give construction people tools that make their lives easier. It is an ambition with a useful built-in demand for proof. A tool has to help somebody do something. After the stock-exchange bell, the larger organization and the change of CEO, there is still a person on a site who needs the right information. Courtemanche has spent a substantial part of his life trying to get it there.