Tomas
Barreto

The Engineer Who Stayed Long Enough to See the Whole Story

Most people arrive at a startup after it has already worked out. Tomas Barreto showed up when Box was still an open question - employee number 14, the fifth engineer to walk through the door. There was no guarantee of a next year, let alone an IPO. He stayed anyway. And when he finally left, more than nine years later, Box was publicly traded, generating over half a billion dollars in revenue, and Barreto had built and led the engineering organization through all of it.

That's the kind of career that sounds tidy in retrospect. At the time, it was a sequence of bets - each one larger than the last, each one requiring someone willing to figure it out as they went. Barreto had joined Box from early roles at IBM and Microsoft, two institutions that teach you process, scale, and what happens when software interacts with the real world. Box taught him something different: what it feels like to build a company's backbone from scratch, with the whole thing riding on whether you get it right.

Before the Bay Area, before Duke, before any of it, there was Caracas. Tomas Barreto grew up in Venezuela, made his way to North Carolina for a degree in Computer Science and Economics at Duke University, and got his first taste of engineering at Shodor - a math and science education non-profit where he interned while still a student. It's not the most glamorous origin story for someone who would eventually sell a startup to Stripe, but it says something about how he moves through the world: drawn to problems that matter, not just problems that pay.

He speaks English and Spanish. He has lived in Caracas, Boston, Raleigh, and the Bay Area. You get the sense that the geographic restlessness mirrors something intellectual - a person always looking for the next version of the problem worth solving.

Nine years is a long time to stay anywhere, especially in Silicon Valley, where two years at a company counts as tenure. But Box was the kind of place that kept changing shape fast enough to stay interesting. When Barreto joined as the 14th employee, the company was still figuring out what enterprise cloud storage even meant. When he left, it had helped invent the category.

He built and led engineering functions across backend, application, and web frontend. He climbed to VP of Engineering, leading teams of 150+ people. He joined Splunk's CIO Advisory Council in 2011, a signal that his thinking was already extending beyond the four walls of Box. And along the way, he contributed to five patents in enterprise cloud collaboration technology - the kind of foundational work that doesn't get headlines but quietly shapes an industry.

The Box IPO in 2015 was the moment that validated years of hard work. Revenue crossing $500 million was proof that the thing he helped build had become real infrastructure for the world's biggest companies. Most engineers would have stopped there - taken the equity, taken the credit, called it a career. Barreto kept moving.

In 2017, Barreto joined Checkr as its first VP of Engineering. The company runs background check infrastructure for employers - a product that intersects with the employment opportunities of more than 70 million Americans with records. It's not the sexiest pitch in Silicon Valley. But Barreto was drawn to the mission: making the process faster, fairer, less of a black box.

He arrived when the engineering, product, and design org was 25 people. He left when it was over 100. That kind of growth - quadrupling a technical organization without losing coherence, culture, or quality - is precisely the work that most companies underestimate until they need it done. Checkr's CEO Daniel Yanisse put it plainly at the time: Barreto "knows what's required in growing and scaling an engineering team."

After years of running engineering organizations, Barreto had a theory: the biggest constraint on software teams wasn't headcount, or tooling, or even technical debt. It was uninterrupted time. Developers do their best work in long, focused blocks - what researchers call "maker time." The typical engineering organization, full of standups and Slack pings and ad hoc interruptions, systematically destroys it.

In 2019, he co-founded Okay with Antoine Boulanger - his former colleague from Box, who had gone on to lead engineering at Google before the two reconnected on this idea. Okay built low-code analytics dashboards for engineering leaders, pulling data from GitHub, Jira, and calendar tools to give teams visibility into where time was actually going. Customers included Brex, Plaid, Intercom, Sourcegraph, and mParticle. Sequoia and Kleiner Perkins both backed the company with $6.6 million in funding.

Then, in May 2023, Stripe acquired Okay. The financial terms were undisclosed, but the strategic logic was clear: Stripe, one of the most engineering-intensive companies in fintech, wanted this capability built into its own operations. It was Stripe's first acquisition since purchasing BBPOS in January 2022 - a rare signal about how seriously the company takes engineering effectiveness as a competitive advantage.