Gonzalo Enei and the problem with standing still

Gonzalo Enei has an opinion about the construction of a Chilean hot dog. The avocado, tomato and mayonnaise should go underneath the sausage. Fewer toppings fall out. Less ends up on your clothes. This is a small rebellion, admittedly, but it has the advantage of being testable over lunch.

He tucked that argument into an essay about buying versus renting a home. A cherished convention deserved a second look, whether it involved property or condiments. He enlisted mathematically minded colleagues to examine the housing question. The hot dog had to make do with his own reasoning.

That habit of reconsidering the arrangement of familiar things offers a useful way into his career. Enei trained as a lawyer, worked in digital media and financial technology, and co-founded Perhaps, the company behind Faces. Along the way, he learned to program. He has kept returning to questions about how work is organized, what people assume they need, and what software might let them do differently.

In May 2026, the arrangement changed again. Enei announced that he was stepping away from Perhaps/Faces. Ignacio Soffia would become CEO; Joaquín Ossandón Stanke would remain CTO. Enei said the founders had made the decision together. The next item on his own agenda was time to decide what came next.

A legal education, then a different brief

Enei studied at Pontificia Universidad Católica de Chile from 2006 to 2012, graduating magna cum laude. His early working life included the law firm Carey. A legal career offered a recognizable sequence of steps. His subsequent choices became rather harder to put on a conventional ladder.

He spent roughly two years at Carey before leaving to build El vaso medio lleno with his sister Paula. The digital media venture concentrated on positive content. It went through Start-Up Chile and reached an interview with Y Combinator. It eventually closed. For a founder interested in reaching people, media supplied a direct education in getting their attention.

Fintual supplied the next opening. After learning that the Chilean investment company had been selected by Y Combinator, Enei contacted its CEO, Pedro Pineda, on LinkedIn. He brought a growth plan to the interview and became employee number 11, working as head of growth. That is a wonderfully practical use of a professional network: write to someone, bring something useful, and see what happens.

The colleague who became a co-founder

Pineda asked Enei to find a designer. Enei contacted a professor he knew at the university’s design faculty. The recommendation was Ignacio Soffia. Years before they would build their own company, a hiring task put the two in the same room.

Their collaboration is visible in a 2021 article they wrote together about Fintual’s investment categories and the behavioral science behind them. The subject was how an interface can help people make decisions. Giving money a purpose changes how people think about it; making a balance especially prominent also changes what attracts attention.

It is an early example of a concern that would reappear at Faces: the container affects the experience. A screen has a point of view. Its labels, hierarchy and defaults make some actions feel natural and others awkward. Enei and Soffia were already thinking about those choices while working on a product people used to manage savings.

The third future co-founder, Ossandón, also came from Fintual. The eventual founding team brought together growth and product experience, design, and software engineering. Platanus lists Perhaps in its 2023 first cohort. The founders were leaving a shared workplace with different skills and considerable familiarity with one another.

Nine weeks on the other side of the screen

In 2021, Enei wrote about taking a nine-week programming bootcamp at Le Wagon. He had been skeptical. A colleague who learned to code and then passed Fintual’s technical interview made the possibility harder to dismiss. Enei enrolled and arranged time away from work to do it.

His account is unusually useful because it resists the instant-transformation ending. Learning enough to build something did not make him an accomplished developer. It gave him a more concrete understanding of the tools and of the limits of his knowledge. For someone working in product and growth, those limits mattered: understanding a technical conversation is different from imagining that you could do everyone’s job.

There was also the pleasure of making an idea behave. The course gave him a chance to work with others on an application. He emerged with a clearer sense of what building software involved, including the friction that a tidy product screen politely conceals. A new skill could change the quality of the questions he asked, even when it did not change his job title.

“I’m a founder and product person.”

Gonzalo Enei · LinkedIn profile

Before the agents, the standing orders

A year earlier, Enei had described a personal finance system intended to take only a couple of hours a month to maintain. He divided the work into categories, scheduled transfers and periodic reviews. The aim was to spend less time repeatedly deciding what should happen to the money.

The essay also contained a wish: he wanted an intelligent being to take the problem off his hands. In 2020, he treated that as a reason to automate what he could with the tools available. Read alongside his later work, it makes a pleasingly ordinary origin for an interest in AI assistance. First there is a recurring chore. Then there is the question of whether you really need to keep doing it yourself.

This is one thread connecting his writing with his startup work. Enei often approaches software through a specific irritation. Repeated transfers, confusing interfaces, static documents and support questions are small enough to describe clearly. Each gives a product a job to do. The difficulty comes when the proposed solution has to fit into someone else’s day.

Perhaps becomes something you can send

Perhaps initially pursued a workspace for collaboration between people and AI. In July 2024, it announced $1.75 million in pre-seed financing from Hi Ventures and Bessemer Venture Partners. The plan included more engineering capacity, model costs and an operation in San Francisco.

The geographical choice mattered to Enei. In a November 2024 conversation about moving from Latin America to the Bay Area, he discussed the attraction of being close to AI talent, collaborators and other founders. His international experience had included childhood time in Tokyo. By February 2026, his interviews were examining both the product and the realities of competing from San Francisco.

Faces gave the company’s work a more concrete object: a piece of content someone could make and share. At its initial rollout, Enei described turning material normally sent as a document, PDF or deck into a visual site. Users could choose a style, supply content and share the result. The proposition began with an everyday business action: sending someone your idea.

Explaining that object became part of the work. In November 2025, Enei wrote that calling Faces “sites” had made people think mainly about homepages and landing pages. “Docs” better conveyed the sharing purpose. The team redesigned the workspace around that understanding. A product name can open a door; a familiar category can quietly close several others.

By February 2026, the emphasis was interactive presentations. The slide could itself be software, with the flexibility that implies. Enei was arguing for a medium people could explore, rather than simply a quicker way to format a familiar deck. His task as a founder included helping users picture what such a presentation might actually be for.

Fifty questions for the new colleague

Enei’s account of installing an AI support agent at Faces offers a smaller, messier view of company building. He selected Intercom’s Fin, used previous conversations to prepare material and organized that knowledge into public articles, internal snippets and instructions about how the agent should respond.

Then came a test set of 50 questions that users had really asked, followed by a co-founder’s attempts to find gaps. The agent needed additions and adjustments. Enei also admitted that he had put it live before completing the full process. The confession makes the anecdote useful: a founder’s enthusiasm can get ahead of his own checklist.

His later observations about work were similarly concrete. In February 2026, he described an office pattern he called “hands-free”: dictate instructions to an agent, wait, review its work and repeat. People could delegate several pieces of work in parallel. The interesting question for him was how that might change the physical setup of a working day, including how much time people spent at a keyboard.

Even an AI company still has payroll, registrations and administration. In a customer account for operations provider Chore, Enei described wanting more time for product, users and investors. The promised relief was recognizable from his old personal finance essay. Work that has to happen can consume the time intended for work you set out to do.

A handover, and an unwritten next page

When Enei announced his departure, he described the company as having growing revenue, a San Francisco team and users who valued the product. Those were his assessments at the handover. He expressed confidence in Soffia and Ossandón and said the founders remained good friends.

Soffia’s own announcement acknowledged their shared decision to leave their jobs three years earlier and build something together. He accepted the CEO role with a sense of responsibility. For a company that had changed its product and its explanation of that product, the next change concerned who would lead it.

Enei’s career makes more sense as a series of working questions than as a march through job titles. How do you reach an audience? How do people understand a financial choice? What happens when you can build the thing you have been describing? What should a presentation let its reader do?

His latest announced plan was to take time before answering the next question. There is something fitting about that pause. A person who has repeatedly reconsidered the default arrangement is allowing himself another look at the options. Somewhere between the law office, the coding classroom and the interactive deck, he acquired the habit of asking whether the familiar order could be improved. Even lunch was fair game.