Sebastian Jimenez, CEO and cofounder of the AI startup Rilla, is giving employees an $18,000 annual housing stipend if they live within a short bike ride of the company's Williamsburg, Brooklyn office. The firm, which builds speech analytics software for in-person sales teams, relocated to the neighborhood in 2026. Jimenez described the stipend as a way to remove friction and help workers spend more time in a creative flow.
The perk comes with intense demands: Rilla employees typically work 12-hour days, six days a week. Jimenez said the startup is also planning to add a gym, sauna, and cold plunge in the office. The CEO, a former stand-up comedian, framed the intense schedule as part of a culture of rapid iteration and improvement.
Jimenez said the investment is worth it for the fastest-growing AI startup, though he did not disclose the company's revenue or valuation. The stipend is intended to offset high New York City living costs while ensuring a deeply committed, on-site workforce. Rilla currently builds tools that analyze conversations to coach sales reps.
The approach raises questions about work-life balance, especially given the grueling hours. Some talent experts argue that such policies can exacerbate burnout rather than boost long-term productivity. The model also risks limiting the talent pool to those willing to live near the office in an expensive market.