This company is letting workers say ‘YOLO’ and work wherever they want for two months

“Biologically, are human beings designed to stay in the bedroom all day long? My view is not,” Besmertnik says about remote work. Whether employees at Conductor will be coaxed off their sofa by a return-to-office mandate or on a monthlong vacation depends on when you ask them.

While Conductor has a hybrid schedule (currently three days weekly in the office), the New York–based company continues to implement some of the workplace flexibility that the pandemic brought white-collar workers. Perhaps the most unique benefit at Conductor is YOLO months, an experimental program that lets employees work wherever they want.

There are currently two YOLO months, one from mid-March to mid-April and the other in August, when children are often out of school. During these months, workers can explore or attend to the areas of their life often ignored during the regular corporate workweek, i.e., family, mental health, and social life. Where employees work can change during YOLO months, but their work hours remain virtually the same to stay in sync with the headquarters’ timezone.

In the age of remote work, this benefit is less innovative or shiny than it once was, since fully virtual employees are technically able to make every month a YOLO month. But as companies navigate a polarizing return to office, this might be a way to appease workers while instituting a slightly new normal at the same time. 

Likening this program to the “icing on the cake” for employees, Conductor’s chief revenue officer Tom Martin explains that in order to stay competitive, companies must get creative. “We are a small company, we’re not paying like Google or Amazon, and we’re in a hot market. So we have to have a leading edge thinking around benefits and work-life balance,” Martin says. 

Flexible benefits are becoming an increasingly valuable tool for companies that want to attract new employees and retain existing ones. But what might create a problem for hybrid employers like Conductor is the most in-demand flexible benefit: remote work.

According to Besmertnik, he came up with the new benefit in early 2021 while on vacation in Costa Rica. 

“I can see why having an experience like this can be life-changing, and I didn’t want to deprive people of that. At the same time, you shouldn’t have to choose between ‘do I want to have this remote experience, but then never have a community’ and the benefits of being part of an office.” 

Not as many employees took advantage of their YOLO months as executives anticipated, according to Besmertnik. Though unsure if Conductor will keep this program or adjust it in the coming years, Besmertnik explains that the motive behind this initiative is to let workers do what fulfills them. And whether that means traveling or spending time with parents depends on the employee.  

Some of those who did travel were able to enjoy flexible hours and sometimes tacked on some vacation days to relax a bit more. And the employees came back with more insight about themselves. 

Sales insight analyst Trusha Patel called her monthlong trip to Portugal a “hard reset” that inspired her to more when she returned home. Spending time abroad pushed Patel out of her normal schedule and allowed her to read and work out more, something she did not do when on autopilot at home.

Tara Fitzgerald, a manager at Conductor, was busy during her YOLO month bouncing between Ireland, Copenhagen, Vienna, and multiple cities in Portugal. She didn’t have as much time to travel as she might have if she had been fully off the clock, but says that having a regular workweek gave her stability and made her more productive so she could have more free time

“Because it’s a set month, you are more likely to do it. Whereas if we were remote for the full year, you probably would never take the trip,” Fitzgerald says, “With millennials, with Gen Z, this will be the future of work. This is very much so going to be the way, flexibility is key. These are the sorts of perks and benefits that people are looking for in future employers.”

Jimmy Moser, corporate and customer success trainer, went to Australia to be with his family. Due to time difference Moser had more of a night shift, and says he was able to “take advantage of the entire daytime.”

Flexibility was the common word among all these employees who took their YOLO months to travel. “To have that freedom to do my work and also to experience a part of the world I’ve always wanted to go to, that was a huge benefit and something I’ll definitely be looking for in any future occupation I fill,” says market development representative Michael LaMarca, who visited Valencia and London.

And being malleable doesn’t cost the company anything. Conductor pays employees the same salaries and benefits while they’re on their YOLO month, points out Conductor spokeswoman Danielle Weiss. 

YOLO month is more of a gesture of sorts, a recognition of the need for employee autonomy while still embracing office culture. “It’s just a great way to show people that you are flexible and you care about their lives outside of work,” says Weiss.