Coworking-Curious? Deskpass Lets You Sample Offices Across the Country

by Brian Nordli
September 9, 2019
Deskpass Ampersand
Photo via deskpass

More than 10 years ago, Deskpass co-founder Sam Rosen found himself in need of an office. 

Rosen ran his web design company, One Design, out of a friend’s New York apartment. The room was littered with piles of clothes on the floor and plagued by poor cell service that caused him to repeatedly drop client calls. Tired of the setup, Rosen did what any budding entrepreneur in the mid-2000s would do — he moved his work to a coffee shop. 

The experience proved to be short-lived, however. The coffee shop didn’t appreciate that he hoarded one of their tables every day and only ordered a bagel and two coffees, Rosen said. Eventually, the outlets stopped working, the Wi-Fi cut out and he needed a new place to work. It was then that his friend urged him to check a new coworking spot, which happened to be across the street. 

At the time, there were only 250 coworking spaces in the world, Rosen said. When he checked in for the first time, it opened his eyes to a new way of working. 

“All of a sudden I was plugged in with cool people in design, politics, technology and media,” Rosen said. “And I just thought it was such an awesome concept.”

After that experience, Rosen sought to replicate it in Chicago, opening up The Coop, the first coworking space in the city, by his account.

As someone in a new environment and new community, coworking spaces offer more value than just a desk and internet access — it’s the community.”

Today, there are more than 200 coworking spaces in Chicago and 35,000 in the world. While WeWork generates most of the headlines, there’s now a vast world of open workspaces, each with their own vibe and community. And as more companies turn to remote working, the need for shared workspaces is expected to continue growing. A study from real estate firm JLL predicts that more than 30 percent of commercial spaces will become flexible workspaces by 2030.

But not everyone needs a monthly membership for a desk five days a week. Some people just need a place to go for a day or two each week to find community, Rosen said.

“It’s easy to feel lonely as an entrepreneur and as a remote worker,” Rosen said. “As someone in a new environment and new community, coworking spaces offer more value than just a desk and internet access — it’s the community. It’s having friends.”

Rosen co-founded Deskpass, a subscription-service platform that connects remote workers to open coworking desks across 11 different cities, in 2015. The website operates similarly to fitness class subscription service ClassPass, allowing users to browse locations and book a desk for a day.   

The technology is based on the Desktime software Rosen’s coworking space, The Coop, had used to manage day-to-day operations. Rosen had designed the software to solve their own challenges behind subscriptions, billing and managing open seats.

Eventually, Rosen realized that as competition between coworking spaces grew, what they really needed was a tool to help them fill their open seats. So, he pivoted and co-launched Deskpass to do just that.


Deskpass Office Seattle
Photo via deskpass

“The number-one thing we learned was that the best way that we could help the industry is to help put butts in seats,” Rosen said. 

Deskpass partners with coworking spaces to track their open desks and conference rooms. They then pay that space an agreed-upon fee when a person fills a desk and provide market insights.

For Deskpass subscribers, instead of gaining access to one coworking space, they gain access to more than 350 spaces in 11 cities. Members can sign up for four, eight or 20 day passes a month, based on their membership fee, and can work in any partner space they want. Through the platform, they can book a room within 24 hours, receive concierge service and access building amenities through its app. 

Some of the more unusual shared work spaces in its network include a mansion, a bouldering gym and Second City, but mostly, users pick their desks based on proximity, Rosen said. Deskpass’ platform then provides booking, concierge service and building access.

The thread that binds them all together is that they work remotely, but they have to change it up from time to time.”  

While Rosen anticipated the company would be most useful for freelancers, it has instead struck a chord with remote workers across all industries. Deskpass is the first coworking experience for nearly 70 percent of its customers, Rosen said.  

“The thread that binds them all together is that they work remotely, but they have to change it up from time to time,” Rosen said. “They’re not looking for a full-time solution but rather for another place where they can switch their routines up and be productive.”

As the demand for coworking spaces has grown, so, too, has Deskpass. The company completed an expansion into Seattle and Portland in August and has plans to expand into Houston and Dallas by mid-September. Eventually, Rosen hopes to grow internationally and provide more partnerships with coworking spaces in suburbs and within underserved communities.   

While the U.S. may just be in the early stages of the remote work trend, Rosen believes people will always crave the community that an office space can provide. Only this time, it’ll be on their terms. 

“To the generations before us, work wasn’t just a thing you did but a place where you would go,” Rosen said. “Today, you don’t have to do your work at your work. I don’t think the office will go anywhere, but we’re seeing people have more flexibility to work where they want and when they want, to be more productive and happier.” 

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