This as-told-to essay is based on a conversation with Sebastian Jimenez, the CEO and cofounder of Rilla, an AI startup based in New York City that builds speech analytics software for in-person sales teams. Rilla relocated to Williamsburg, Brooklyn, in 2026. The essay has been edited for length and clarity.
I started Rilla in 2019 because I became fascinated with the creative process.
I used to do stand-up comedy in college, and I loved the idea of trying something, failing, getting feedback, and improving. That’s what building a startup feels like.
That same mindset is part of why we now offer employees an $18,000 annual housing stipend if they live within about a 10-minute bike ride of our Williamsburg office. We want to remove friction from people’s lives so they can spend more time in the flow.
We’re one of the fastest-growing AI startups, but we’re not trying to replace people. We’re building what I like to call an Iron Man suit for salespeople.
That same philosophy shapes how we think about our own employees.
The flow state
Rilla has what many people would call an insanely hardcore culture.
I was deeply influenced by the book “Flow: The Psychology of Optimal Experience.” The central idea is that one of life’s purposes is to spend as much time as possible in a state of complete focus and immersion. That’s what we optimize for.
We believe at Rilla that we need to create an environment where our employees are in the flow almost 100% of the time.
Our employees typically work 12-hour days and come into the office six days a week. We don’t clock people in or out, and we don’t force anyone to work here. We select people who want this kind of environment. Many of them are former Division I athletes, entrepreneurs, or people who have always pushed themselves to perform at a very high level.
I think those hours help cut out a lot of the extra fat in life. When you spend that much time working, you become much more intentional about how you use the rest of your day.
The new office space
As we grew to around 120 employees, we realized something was working against us: our office.
Most commercial buildings have sealed windows, which means CO₂ builds up throughout the day. Once CO₂ levels climb high enough, studies have shown cognitive performance can fall significantly. People think they’re tired at 3 p.m., but often it’s because they’re breathing stale air.
That realization led us to hire Dr. Joe Allen from Harvard, one of the world’s leading experts on healthy buildings. We toured around 20 offices looking for one with exceptional ventilation.
We eventually signed a 10-year lease for the entire penthouse floor at 25 Kent in Williamsburg because it has what Dr. Allen told us is the best ventilation system he’d seen in New York City. Clean air may sound boring, but if your business depends on creativity and focus, it matters.
Our benefits pay off
Every benefit we offer has one purpose: helping people stay healthy and spend more time doing meaningful work.
We’re not trying to coddle people. A lot of companies offer perks that end up distracting employees. We ask ourselves, “Can this help someone get into the flow?”
That’s why we pay for three meals a day. It’s why we’re building a gym with a sauna and cold plunge. And it’s why we offer employees an $18,000 annual housing stipend if they choose to live within about a 10-minute bike ride of the office.
Commuting is one of the most annoying parts of people’s day. If someone works 12 hours, sleeps eight hours, and works out for an hour, they don’t have much free time left. I’d rather they spend that time with family, reading, or doing something meaningful than sitting on a subway.
Altogether, we spend roughly $37,000 per employee each year on housing, meals, and fitness benefits before you even include healthcare, retirement benefits, or equity.
We’re fortunate that we can afford to invest that much because we’re an extremely capital-efficient business. Each engineer generates roughly $4 million to $5 million in annual recurring revenue.
The housing stipend is optional, but about 80% of our employees take it.
Our goal isn’t simply to get people into the office. It’s to build an environment where they can do the best work of their lives. And if they stay at Rilla long enough, they usually end up pretty ripped, because they’re eating well, working out, and spending their days in a culture that takes performance seriously.
Read the full article here
