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In a surprising and rather unconventional move, Roy Lee, the CEO of tech startup Cluely, has introduced a welfare initiative that’s grabbing national attention — and it’s not about bonuses, healthcare, or work-from-home flexibility. Lee recently announced on social media that Cluely employees can earn $500 for successfully setting up a coworker on a date. Under certain conditions, that incentive could even reach $1,000.
Yes, you read that right. Love — or at least the pursuit of it — is now part of Cluely’s workplace culture.
The policy, dubbed informally by some as “Cupid Cash,” is part of what the company is calling its expanded Welfare Policy. According to Lee’s post, the core idea is to promote happiness, emotional wellbeing, and stronger social bonds among employees — all while having a little fun in the process.
“Relationships matter, both at work and in life,” wrote Lee. “We support our team members’ career goals, health, and personal growth. Why not their happiness too?”
How It Works
The mechanics of the policy are as unusual as the idea itself. An employee who successfully arranges a date for another colleague is eligible for a $500 reward. If the date goes well — for instance, leads to a second date, or shows signs of genuine connection — the reward can go up to $1,000. There are no requirements for long-term outcomes like relationships or marriage, just that the date is sincere and consensual.
The initiative relies on mutual trust and HR oversight to ensure transparency and avoid any ethical pitfalls. Lee emphasized that participation is entirely voluntary and is meant to be light-hearted, inclusive, and respectful.
Going Viral
Lee’s announcement on social media quickly went viral. Screenshots of the policy post have been widely shared on platforms like X (formerly Twitter), LinkedIn, and Reddit. Many users praised the idea for its creativity and for prioritizing employee happiness in a novel way.
“It’s so out-of-the-box that it might just work,” wrote one commenter. “We always talk about work-life balance, but this is literally helping people with their life.”
Others have been more skeptical, raising questions about privacy, potential pressure to participate, and workplace boundaries. Lee responded to the feedback in a follow-up video, assuring viewers that the policy was implemented after thoughtful discussions with Cluely’s HR and legal teams.
“It’s meant to be fun and safe,” he said. “We’re not trying to play matchmaker aggressively. We just want to add a spark of joy to our team’s lives.”
A New Era of Employee Welfare?
Roy Lee has become known in startup circles for his unorthodox approach to leadership. From hosting monthly “innovation sleepovers” at Cluely HQ to implementing a “No-Meetings Friday” rule, Lee has often prioritized culture as much as productivity.
This latest initiative, however, marks a new territory: blending emotional and social wellbeing into corporate policy. While some experts see it as a bold step toward holistic wellness, others caution that such personal initiatives require clear boundaries.
“It’s a fascinating experiment,” says Dr. Hannah Reed, a workplace culture consultant. “Done right, it can create bonding and trust. But companies must ensure it doesn’t blur professional lines or create unintended pressure.”
What’s Next?
According to Cluely’s HR department, several employees have already expressed interest, with a few early match-making attempts underway. The company plans to monitor the results and gather feedback to see if the policy should be extended or adapted.
Whether or not other companies will follow suit remains to be seen. But one thing is clear: in a time when workplace culture often feels sterile or overly formal, Roy Lee is injecting a bit of heart into the business world — quite literally.
As Lee put it in his closing remark, “If we can help someone find joy — and maybe even love — while building amazing products together, that’s a win-win in my book.”
