Meet the startup that grew from $0 to $40m ARR in just 3 years
Behind-the-scenes with Rilla
✨ Hey there this is a free edition of next play’s newsletter, where we share under-the-radar opportunities to help you figure out what’s next in your journey. Join our private Slack community here and access $1000s of dollars of product discounts here.
Try to imagine your dream job.
When you think of the culture of the organization you’d be joining, what do you picture?
Do you see it as fun and uplifting? Or do you see it as intense and hard-working?
“Founders often think these two ideas are opposite. Mutually exclusive. They're wrong.”
That’s what Sebastian Jimenez, the founder and CEO of Rilla, told us as he started describing their (very unique!) company culture.
Rilla has become the leading “conversation intelligence software” for in-person sales. Think HVAC, real estate, automobile, and windows. Rilla has grown from $0 to $40 million ARR in just 3 or so years, and is still growing at 15% month over month. That makes them one of the fastest growing startups of all time.
The main cause of their success?
The Rilla team would say it’s been their culture.
“The culture is the magic at Rilla.”
“We’re ruthlessly intense at Rilla (think 12-hour workdays, 6 days per week in the office). But we’re also insanely generous and devoted to fun.”
To dig into the details as to what that sort of high performance, high satisfaction environment looks like, we thought it would be interesting to go a bit deeper with Sebastian and the rest of the Rilla team. In this Next Play Spotlight, we find out what it’s like to work at Rilla.
(Also, they are hiring in NYC for roles in every department: engineering, growth, sales, operations, people. You can apply here.)
Major thanks to the Rilla team for sharing behind-the-scenes details and supporting Next Play.
You have probably heard the phrase “work hard, play hard”—but what does that really mean? And how does it translate into working productively at a startup? Productively being the key word. How do you actually get results? Great results?
Well we could start with the first part: “working hard.”
Some people think that cleverness or intelligence alone is enough to achieve success. And perhaps sometimes in certain domains it can be. But the team at Rilla, while they’ve got plenty of people with impressive resumes boasting backgrounds from Ivy League schools, makes no mistake about it: they see hard work as a pre-requisite to success. You obviously want to approach things in a smart way—but there’s no replacement for hard work. If you want your startup to win, you have to put in the hours.
And so, the Rilla team works hard. Very hard by most startup standards. It’s not your typical 9 to 5 that’s for sure.
“I get into the office between 9 and 9:30am. I usually leave between 9 and 10pm.”
“We expect people to work around 70 hours a week, and everybody is in person.”
But they are not trying to be like a bank that just works hard for the sake of it. They are not just trying to waste hours for no particular point.
“We’re not an investment bank or a sweatshop. Cultivating intensity is not a ‘grindset’ thing. We’re pursuing greatness, and greatness requires obsession.”
They’ve architected much of the company culture around helping their team unlock high performance productivity. Around helping people become the highest and best versions of themselves. And they’ve approached this in some rather unique ways (with aspects we have not really seen at many if any other companies).
For example, to encourage working more, they will cover $1500/month of your rent if you live within 10 to 15 minutes of the office. (Sebastian also lives right by the office and walks to work everyday!)
This sort of hard work mentality is a big aspect of what they look for in candidates.
And they’ve found a good way to identify this is to find people who like to work hard in multiple areas of their life, not just in the office.
Like for instance the personal health and fitness domain. 25% of their team are former division 1 college athletes.
“If the athlete in you is desperate to stay alive, you know where to find us.”
“If you were the best rower on your team, the fastest sprinter on the track, the captain who pulled your team through hell and back…this is where your fire keeps burning.”
They have a gym in the office and also cover a $300/month gym membership (or personal trainer).
This is all because they are trying to build the perfect environment for high achievers. For people who really approach life with a growth mindset.
But hard work alone is only half of Sebastian’s culture equation—they also invest a lot in the “fun” aspect of work.
They also do a bunch of activities together. One popular one is they have a Saturday run club and also several intramural teams. They’re also in the process of installing a Sauna and cold plunge in their office.
Rilla is probably not a good fit for people who want a huge separation between work and personal life.
“People that have strict boundaries between work and personal life, and are unwilling to compromise, are probably not a fit.”
That’s because the Rilla team spends a lot of time together.
“We work from 8am to 8pm and play Smash from 9pm to 2am. We work for 10 hours, go to the gym (we give all of our employees a gym stipend), then work again until midnight. We work 6-day weeks at an office with an arcade, unlimited snacks, and cool people.”
This has led to strong bonds forming across the company. The types of relationships that are high trust in nature.
It feels very different from a typical work environment. You’ve probably worked at a company where people have more or less checked out. Where they clock in, do their work quickly, and leave. Where there is no real commitment to the cause.
You can just feel the stagnation in conversations with people. Do their eyes light up when they talk about the mission of the company? Do the vibes feel uniquely and highly productive? Or do things seem to be slowly dying as people no longer feel like they are making an impact?
The team at Rilla raves about Rilla. In a way that you can feel and see in their words. They really just love working on the company.
“I think a part of what makes working at Rilla so fun is that I genuinely found some of my good friends at the company - to the point where I want to hang out with them outside of work.”
It has also led to people forming a very strong commitment to the company, and to one another. In a long-term sort of way.
“One of the things I'm most impressed by at Rilla (and hope to emulate when I start my company one day) is the people we hire. They care so much about the company and each other, push me to grow, and overall are just fun, chill people who I would be friends with even without Rilla. We have a lot of fun - it often just feels like building cool stuff together with your buddies.”
And because there is huge buy-in from the team - leadership is great about delegation. They trust people to be responsible for their work. They treat their team as owners, and expect them to act like a founder when making decisions.
“Take full ownership over everything that is handed to you. Try your absolute best to have all the work that you produce be of the highest quality you can give.”
Much of the company has expressed interest in starting a company one day in the future. They see Rilla as a sort of training grounds for that. A place to test their skills and learn best practices that they could one day apply to a company of their own.
They see their team as people who are willing to go above and beyond the typical job description.
“My days are a fast-paced mix of customer calls, hands-on product building, quick pivots between high-level alignment meetings and deep coding sessions. Engineers here don’t just ship code—we drive full product ownership, from engineering design, to product direction. As the engineering lead for our realtime project, I spend each day relentlessly moving the project forward, balancing strategic vision with the grit of building and iterating at startup speed.”
“I visited a key customer to launch a product I’d built and gather live feedback. During the demo, they asked for a feature that would give them deeper insights. Driven by customer obsession, I immediately locked myself in a meeting room and worked late into the night to deliver the new feature—shipping it the same day. When I showed it to them the next morning, they were amazed by the speed and dedication. This hands-on approach helped us collect richer feedback and rapidly move the product forward.”
“There are no PMs here: you and your engineering peers will lead projects from discovery all the way through feature design and implementation. You’ll onboard customers to early prototypes, gather feedback, and iterate rapidly to build what truly matters.”
What makes this sort of culture work well is that they’ve also built an organization that embraces radical transparency and honesty.
“Everyone has access to everything, financials, customer data, etc. Get to learn so much more about what's going on in the company and feel confident.”
“If you notice something, have an idea on how to do things better, share it. The quicker you fail the quicker you learn.”
They even go as far as to host a weekly ritual where people transparently share their mistakes and lessons.
“We have a ritual “f*ckup friday,” where everyone goes around sharing how they messed up that week and we clap and celebrate them. This is part of moving fast + not being afraid of failure. We talk about the top f*ckups during all hands, and it's celebrated by the whole company.”
It’s not just transparency for the sake of it—the idea is that sharing things honestly leads to faster feedback loops and more productive learning. They want people to realize that what really matters is slope—it’s not about where you start but rather how quickly you can improve.
“Don't be scared to make mistakes, most are reversible and if not, don't matter much / learning is more valuable in the grand scheme of things.”
“Embrace imperfection, ship things as early as possible, getting feedback and iterating gets you to great faster”
This has created an environment where people learn and adapt quickly. Rilla has hit a revenue growth curve that really provides a lot of opportunities for people on the team to step up, take ownership, and try to make an impact. Because of that, and their focus on long-term outcomes, it seems like a great place to learn a lot, very quickly.
“I can't imagine a place where I could've learned more at these last 2.5 years. If you want to be a founder or just 10x your growth, this is one of the places that rewards you for that hunger and gives you learning opportunities - not limited to your domain.”
“Learning: lots of folks on the team have been hired for a certain role, and then following their curiosity they get to shape their own path. For me, it was from pure engineering to a hybrid of product / design / eng. For Will Gao, he went from an early engineer to now leading growth and marketing. For others, they went from sales to recruiting, etc.
If Rilla’s culture and work interests you, they are hiring in NYC for roles in every department: engineering, growth, sales, operations, people. You can apply here.
And if you are looking for additional job opportunities, you can check out Next Play here.
So, nobody with kids works there. Got it.
This is a horrible article. No room for adults with kids, are sleeping less than 5 hrs a night, and play Super Smash Brothers while working out.