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This AI startup CEO gives his employees rent stipends—but he warns the benefit isn’t for everyone

Brit Morse
By
Brit Morse
Brit Morse
Leadership Reporter
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Brit Morse
By
Brit Morse
Brit Morse
Leadership Reporter
Down Arrow Button Icon
July 11, 2025, 8:45 AM ET
Rilla employees working at their office in Long Island City, New York
Rilla employees working at their office in Long Island City, New York.Rilla

Good morning!

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Earlier this week I had an interview with one of the most hustle culture-driven founders I’ve talked to in a long time. 

Sebastian Jimenez is the CEO and cofounder of Rilla, a software company that provides transcription solutions for sales and service teams. He doesn’t believe in work-life balance and expects his roughly 80 employees to put in at least 70 hours per week in-person at the office. That’s a big ask, but the company offers competitive compensation and some niche benefits to sweeten the deal.

In addition to traditional benefits like medical, the company expenses gym memberships, covers at least two meals per day and pays for Ubers should employees stay late. But there’s one benefit in particular that stands out from the rest: If an employee chooses to live within a five to 10 minute commute from the office, they get $1,500 a month towards rent. 

That’s certainly a tempting proposal given the high costs of New York City rent. But Jimenez says that’s not the point. The real aim is to get employees into the office for as much time as humanly possible. So far, around a dozen workers have taken Rilla up on the rent offer.

“If you live 30 minutes away from the office, that’s an hour a day that you could be working,” says Jimenez, who also lives within a short walk to the office.    

That kind of live-to-work ethos isn’t for everyone, and Rilla is also very clear with prospective employees about what’s expected of them. But it is an example of a company with a particular world view that created benefits to reflect that. 

“This is by no means the way to run every startup,” says Jimenez. “This is just the way it works for us.”

You can read more about Rilla’s rent stipend here.

Brit Morse
[email protected]

Around the Table

A round-up of the most important HR headlines.

After years of leaning into their corporate careers, many highly successful women are opting out of the workplace, on their own terms. New York Times

In a change from its previous stance, the EEOC plans to process complaints filed by transgender workers, though they will be under heightened review. Washington Post

In the frenzied world of private-equity recruiting, recent graduates who have barely started their first gigs as analysts at big banks are already competing offers for years down the line. Wall Street Journal

Watercooler

Everything you need to know from Coins2Day .

The office crunch. This year will likely bring further pain for office values across all major metros, but a sharp regional divide is set to emerge. —Ashley Lutz and Coins2Day Intelligence

New slang. Here’s the list of some terms Gen Z says they’re currently using that older generations ought to know, if they don’t already. —Orianna Rosa Royle 

The future of tech. During a recent demonstration, Elon Musk said that in the near future, humans will no longer be managing the economy. —Christiaan Hetzner

This is the web version of Coins2Day CHRO, a newsletter focusing on helping HR executives navigate the needs of the workplace. Sign up to get it delivered free to your inbox.
About the Author
Brit Morse
By Brit MorseLeadership Reporter
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Brit Morse is a former Leadership reporter at Coins2Day, covering workplace trends and the C-suite. She also writes CHRO Daily, Coins2Day’s flagship newsletter for HR professionals and corporate leaders.

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