Sebastian Jimenez is making physical proximity a line item at Rilla: the CEO and cofounder told Business Insider that Rilla offers employees $18,000 a year if they live within roughly a 10-minute bike ride of Rilla's Williamsburg, Brooklyn office.
The stipend is optional, according to Jimenez, and about 80% of Rilla employees take it. Rilla also pays for three meals a day and is building a gym, sauna and cold plunge in its office building. Jimenez told Business Insider the package costs roughly $37,000 per employee each year before health care, retirement benefits or equity.
That math only makes sense because Rilla is built around an unusually demanding operating model. Jimenez said employees typically work 12-hour days and come into the office six days a week. Rilla does not clock workers in or out, he said, and hires people who choose that environment. The housing stipend turns that culture from a slogan into a system: if Rilla is going to ask employees to spend most waking hours at work, Jimenez wants to eliminate the commute.
Jimenez started Rilla in 2019 after becoming interested in the creative loop he saw while doing stand-up comedy in college: try, fail, get feedback, improve. That same loop sits at the center of Rilla's product. Rilla records in-person sales conversations, transcribes them and gives managers a way to coach reps without physically riding along on every customer visit. The company describes its software as AI coaching for in-person sales teams across offline industries.
A benefits policy built for a 72-hour week
Jimenez frames the housing stipend as infrastructure for his preferred work system, not as a perk.
Jimenez told Business Insider that Rilla optimizes for flow, drawing from Mihaly Csikszentmihalyi's book "Flow: The Psychology of Optimal Experience." Rilla's internal version of that idea is physical: put employees near the office, feed them, build fitness into the building and reduce the number of hours lost to subway rides or errands.
Rilla's policy also works as a sorting mechanism. A candidate who wants remote flexibility or a conventional five-day schedule will screen out. A candidate who wants a high-hours, high-contact environment may see the stipend as part of the compensation package. For Rilla, that is the point. Jimenez is not trying to make office work look casual. He is making a specific promise: Rilla will remove daily friction for employees who accept Rilla's pace.
The trade is explicit. Workers who take the stipend get cash toward rent and more time near the office. Rilla gets a workforce clustered around Williamsburg and available for the kind of in-person tempo Jimenez believes improves execution. The unanswered question is durability. A culture optimized for short feedback loops can compound quickly, and it can also burn through people if the work model becomes the product rather than the way to build it.
Rilla's office move is part of the same bet
Rilla relocated to Williamsburg in 2026 and signed a 10-year lease for the entire penthouse floor at 25 Kent, according to Business Insider. Commercial Observer put the lease at about 57,350 square feet, noting Rilla took the eighth-floor penthouse and nearly 4,000 square feet of private outdoor space. The Real Deal reported in January 2026 that the asking rent was $76 per square foot.
Jimenez's explanation for the move is unusually operational. He told Business Insider that Rilla hired Dr. Joe Allen from Harvard to advise on healthy buildings and toured about 20 offices in search of better ventilation. Jimenez said Rilla chose 25 Kent because Allen told Rilla it had the best ventilation system he had seen in New York City.
The ventilation argument matters because it shows how far Jimenez is willing to take the premise. He is treating the office as a production environment, closer to a training facility than a leased workplace. Air quality, commute time, meals and fitness are inputs in the same model.
The office reports also show the real estate side of the AI boom. A high-hours AI company willing to sign 10 years in Brooklyn is valuable to landlords trying to fill premium space. Rilla's culture gives Global Holdings, 25 Kent's manager, a tenant story that fits the building: AI, growth, in-office work and a workforce willing to move with the company.
The product explains the founder's obsession with proximity
Rilla sells AI coaching for sales conversations that happen offline, where older conversation-intelligence software had less visibility. TechCrunch reported in 2022 that Rilla, then called Rillavoice, raised a $3.7 million seed round led by Crew Capital, the venture firm co-founded by UiPath co-founder Daniel Dines and Brandon Deer. At the time, Jimenez described the opportunity as a gap in sales software: most sales tools were built for Zoom, phones and digital workflows, while many reps still sold face to face.
That wedge has become more crowded. Siro pitches AI coaching for in-person sales teams and advertises live coaching during sales calls. Listel positions itself around enterprise in-person conversation capture and compares itself against Rilla, Siro, Gong, Chorus and Salesloft. Balto serves the adjacent contact-center market with agent assist, QA automation, coaching and insights.
Rilla's cultural design tracks the product category. Jimenez is building software for managers who believe performance improves when real conversations are captured, reviewed and coached. Internally, he is applying the same belief to employees: reduce noise, increase repetition, make feedback constant and keep the team close enough to move fast.
Jimenez told Business Insider Rilla can afford the benefits because each engineer generates roughly $4 million to $5 million in annual recurring revenue. That is a company-supplied figure, and Rilla has not disclosed enough financial detail to independently test the denominator behind it. Taken as Jimenez's own benchmark, it explains why he sees housing, food and fitness as investments rather than perks. If an engineer is producing that much ARR, a five-figure housing stipend is a small retention and productivity expense.
The risk is that a benefits package designed to sustain extreme work can also normalize extreme work. Rilla's housing stipend is generous cash compensation for employees who already want the model. It is also a reminder that the AI startup labor market is splitting: some founders are using flexibility as a recruiting edge, while Jimenez is using proximity, intensity and a dense office culture as his edge. Rilla's bet is that the right employees will choose the second path, and that the company can keep them long enough for the work to compound.