From gritty to pretty: 6 startups share their office Cinderella stories

Sam Dewey

Rise Interactive, a data-driven digital marketing agency, is no stranger to the perennial growing pains many startups endure. At one stage in their growth, they even put desks in their main office entrance and transformed their conference room into a makeshift office — for 10 employees. 

"It was an exciting time," said Scott Conine, SVP of Operations, "but we are glad to be able to spread out a bit more these days." Rise Interactive's old office space at 325 W. Huron

How would you describe your old spaces?

Our first office was located in Founder and CEO Jon Morris’ home — and I worked out of the laundry room. In 2005, we moved to our first office in Chicago’s Loop. It had a conference room, a few hand-me-down desks, and space for about 10 employees. A lot has changed since then! We’ve continued to outgrow a number of office spaces and now take up 40,000 square feet in our current 1 S. Wacker location.

What have you learned about your company’s culture as you’ve transitioned to bigger and better office spaces?

As a fast-growing company, we’ve had more than five different office locations and have undergone a number of expansions. Since we are moving and growing at such a fast pace, we’ve been able to optimize the space accordingly and continue to cultivate our working environment. We’ve learned a lot about what we like and what works for us, and have continued to evolve with each office.

For instance, when we were in our fourth space, we had grown to about 50 people in 3,500 square feet. And you know what we loved about it? The energy was palpable. We’ve always had really open floor plans; we love to collaborate, and we’ve tried to recreate this energy within every office space. When someone walks off the elevator and into our office, we want them to feel that energy is bubbling out of the space.

We’ve also learned that we enjoy being together. In one expansion, we added office space on an additional floor that had to be accessed by elevator. It was our first foray into a split floor plan — and we didn’t like it. It’s why we built a stairway to connect our third and fourth floors in our most recent expansion. And now, that stairway has become the Grand Central Station of the office.

What has the journey from office “rags” to office “riches” felt like from the inside?

Looking back, I still value our experience and what we went through with each office. It keeps us honest and true to our roots. We were willing to do anything — even build plywood cubicles in our third office — and not think anything of it. I want to try and help people remember that this has truly been a journey and a really fun, strange trip.

How's it feel to be in your new space?

It feels like home. And that’s the beauty of our growth. While we’ve been in several locations, it’s important for us, no matter where we are, to cultivate a sense of belonging. I’m proud of how we’ve continued to evolve within each space and look forward to seeing how we will continue to enhance our work environment to make an even better and more enriching space for our employees.

kCura's iconic green couch

Sometimes, the stories and culture you build in the beginning stick with you — and kCura couldn't be a more literal example of that. As the company's Chief People Officer Dorie Blesoff tells it, during one meeting at the e-discovery software's old office, kCura's CEO Andrew Sieja summarized the company's mission into two simple words — "Don't Suck." One employee decided to immortalize that saying on a post-it note and stuck it to their then-communal mission statement — which can now be found hanging in the VP of Operation's office, Post-it note and all. 

How would you describe your old space?

Even though our old spaces might have seemed like a mess—we were all on top of each other, and it was hot, and loud, and sweaty—there was something special about the atmosphere because we were all together. There was a lot of interaction, and it was fun—it was part of the struggle. The design of our new office is deeply grounded in the collaborative, entrepreneurial spirit of our early days. That ideal is probably best seen in our green couch—it’s been with us through five moves, it’s been used as a bed, a game room, a waiting room, and an intern’s desk—but it reminds us to be humble and stay hungry.

Did you learn anything insightful about your company's culture as you've transitioned to bigger and better office spaces?

We’ve been able to grow into new offices because of the opportunities in the marketplace, and it’s great to see our business continue to expand at a rapid rate. However, even in a state of high growth, we prioritize hiring people whose personalities and work ethics align with our core values. And even though we’ve grown from 11 to over 500 since 2006, we still listen to what our team needs or wants to work better—whether it’s standing desks or new arcade games.

What's the journey from office "rags" to offices "riches" been like from an insider's perspective?

We’ve always been good at being humble and doing more with less—so we’ve always seemed to have the right environment for the company we are at any point in time. We’ve always had the best equipment we could afford at any given time, knowing that great technology can enable great work, and added amenities that attracted and retained great talent, were actually useful for our team members and stuff they wanted, and made collaboration easier. It’s more about creating an environment that fosters collaboration and having a good time at work than having the most striking office with the most ridiculous amenities. The journey’s been fun—and we love us some Ms. Pac-Man—but it’s been more about the people than the stuff. And with those people, it feels like with each move, we’ve been able to become more. We started off as a company of obscurity, and in our small, maybe over-crowded office, we became a company of relevance. With the opportunity to move to new offices—building a bigger team of people who value doing more with less—we wanted to become a company of significance. And with our team in the space we have now, it feels like we’ve reached that goal. It’s exciting to think about what comes next.

How's it feel to be in your new space?

Looking back at our office from 2008 when we worked side-by-side in a small room, not too much has changed—we kept that same focus on collaboration and flexibility when we designed our new space as an open floor plan, and our product management, product marketing, and product development teams all sit together to promote effective communication between departments. We may have come a long way from using the couch as a desk, but it helps us to stay hungry when we hold true to our humble beginnings.

Fieldglass's Naperville Office

When you're a young company, sometimes you can be a little more flexible with the rules. Take vendor management software provider Fieldglass. Their first office, for instance, was known to have dogs visit from time to time. 

"Our former CTO Sean Chou would bring his dog, Simon, to work," said Jeff Basso, VP of Information Technology who''s been with Fieldglass since 2001. "We were unaware of how many people are terrified of dogs, even docile ones like Simon. It sure weeded out our interviewees fairly quickly as Simon had to check out each new person entering the office." 

How would you describe your old space?  

It was much like your very basic corporate office — a bit stuffy, but functional enough to get the job done. Hey, it was better than the apartment Fieldglass shared for its very first space.   

Did you learn anything insightful about your company's culture as you've transitioned to bigger and better office spaces?   

Fieldglass understood that its offices are a piece of who we are as an organization. We feel that our spaces should give us a place to grow and change, but also be a place that is deeply rooted as a presence in the community, like the Fifth Avenue station connected to our Naperville office.   

Fieldglass's Chicago office    

What's the journey from office "rags" to offices "riches" been like from an insider's perspective?  

I am not sure about rags to riches. Our Naperville office is a 100+ year-old building that was once a furniture factory. We love its architecture, and are committed to keeping with its style. We were lucky the building had good bones, but that said, it took all parties to envision what was possible. In addition, our new office in Chicago really copies the idea of creating a space that is welcoming and comfortable to employees.

How's it feel to be in your new space?

It is home. There are always things we want to change, but we are not one to look back — the question is what are we going to do next. We were recently purchased by SAP, and hope that we have given them the “bug” of what is possible when it comes to new spaces as we continue to grow.

The spiral staircase in the entrance of GrubHub's office

Leave it to GrubHub, one of Chicago's original success startup stories, to also have one of the classic humble beginnings startups are known for. According to Abby Hunt, GrubHub's Director of Public Relations, the company originally worked out of co-founder Mike Evans' apartment after he quit his job to give coding full attention. As they say, the rest is history. 

How would you describe your old spaces?

We’re on our fourth office now. After they moved out of Mike Evans' apartment, they moved to a smaller place in Lincoln Park for a while, until the team got up to about 20 people. Then we moved to a warehouse on the corner of Elston and Webster. When I joined, we were the entire first floor and the entire fourth floor. At that time, we’d grown to almost 350 employees. We were most definitely at capacity. Towards the end, it just got really congested. You could tell we were at a tipping point — we just didn’t have any more desks!

Did you learn anything insightful about your company's culture as you've transitioned to bigger and better office spaces?

I think a good word is “scrappy.” One thing GrubHub is very good at is being very conscious where money is being spent. You want to create an atmosphere that retains the best talent, so you always need to do some work, but when you’re starting out, the people most invested in joining a startup are aware that cool office spaces are not necessarily top of mind. The chairs don’t all need to match. But there can still be unique elements that help shape culture, like our office at Elston and Webster office. It was an all open environment, which was really great for collaborating with people and building a sense of community. 

What's the journey from office "rags" to offices "riches" been like from an insider's perspective?

It’s definitely loosened up. We’re now a publicly held company, so there’s a lot more at our disposal. But it’s still about making smart decisions. We take risks, but we’re always very conscious of the risks that we take. When we think about the money being spent or the resources that are being used, we’re conscientious. We don’t go crazy — because we haven’t always had that at our disposal. We have employees who can do a lot with very little. And then, when you give those employees a lot, they can do even more. Doing a lot with a little is something we’ve brought with us through each office. 

How's it feel to be in your new space?

The building we’re currently in is definitely more formal, but it has retained some of that scrappiness from our old office. Historically, our office used to be an architectural firm, so the space itself is incredibly unique. We have high ceilings and a spiral staircase leading up to the 22nd floor where we have a rooftop, which — as far as I know — is one of the few rooftops available in downtown Chicago. There’s WiFi available, so in the summer we all use it for meetings, lunch, and happy hours. It’s a great place to get away from your desk. It’s still that same open atmosphere — we’ve just moved it outside. 

Hireology's office today

Startup offices can be small, but when you see explosive growth the rate at which Hireology did, things can get crowded — fast. At Hireology, it got to the point where the company's VP of product would throw a "shush ball" at salespeople who got too loud on the phone. 

"The space was so small that we would hold large company meetings in the McDonald's across the street complete with $.49 ice cream cones!" said Erin Borgerson, the company's director of marketing and employee number three. 

How would you describe your old spaces?

Hireology has called 3 different offices home. Our first office was located in the hallway of Homescout Realty in River North. It consisted of several rows of desks strategically placed to avoid a fire hazard. We crammed around 15 people into this hallway until we were basically sitting on top of each other. My first month on the job, me and a few others stayed late to build Ikea desks for new employees. A new employee even received a "desk" that was really a door over two filing cabinets. We didn't care though because our culture was so tight!

Our second office and first real independent space was a floor below the hallway. It felt big when we moved in, however after 8 months we crammed 50 people into the space. At times it got so hot, that people resorted to sitting and working in the hallway.

Finally, we moved into a giant space in River East that truly feels like home. There is room for everyone to sprawl out and get work done. The funny part is people seem to enjoy working close together and feeding off each-other's energy.



Did you learn anything insightful about your company's culture as you've transitioned to bigger and better office spaces?

Our company loves to feel close and family-like. We would not do well with cubicles and offices as most people enjoy working directly next to each other and bouncing ideas off one another. Also, there is a sense of camaraderie between the people that have endured the small offices and are now together at the large space, we've been through thick and thin together!

What's the journey from office "rags" to offices "riches" been like from an insider's perspective?

I never looked at our old offices as "crappy", I was just so happy to do a job I loved with people I loved even more. I think most people felt that way. We knew there was a job to get done and it didn't matter where we did that job.

How's it feel to be in your new space?

Truly incredible. It was a blast to see the team's faces when they walked in for the first time. We now have a view of Navy Pier and the Chicago River, a fridge stocked with beer and caffeinated beverages, and a professional ping pong table.

Signal's new office — with plenty of room to grow. 

Signal didn't become a leader in cross channel marketing technology without an ounce or two of creativity. So when they starting outgrowing their old space, they thought far outside of the box to come up with some solutions, including turning a storage closet into a conference space, aptly named the "creepy room." To make room, some employees gave up desks entirely. 

"At the end of our run there, several of us even gave up our desks to make sure new people had a place to sit," said Lisa O'Keefe, Vice President, Talent and Culture. "We became the nomadic people of Signal and carried our belongings to whatever open desk we could find."

Signal's older, more crowded office

How would you describe your old space?

Before moving to our current spot at 111 N. Canal, we were in a loft space at 440 N. Wells. When we first moved there in January 2012 it felt huge, filled with promise and ugly carpet. There were 30 of us. It was near 1871, BowTruss and so much happening in the Chicago tech world. The location, exposed brick, and view of the Brown line all felt developmentally appropriate for us.  

However, we outgrew it quickly and by the time we moved in November 2014 it was beyond cramped for 120 of us. We felt stifled and that we’d not just outgrown the space physically, but emotionally. We were ready to have our own bathrooms, amenities in the building, and to be closer to more varied public transit. Our new space delivers on all of these!

Did you learn anything insightful about your company's culture as you've transitioned to bigger and better office spaces?

Definitely. We have learned that the bigger the office space, the more we all need to work to foster a sense of closeness and communication. When we were in one big room, it was easy, for example, for our developers to hear the client services team talk about a problem and jump in to assist or test a new feature. Now, we are more spread out and different teams are separated by our fantastic kitchen and common area. We’ve had to adjust to make sure that teams stay connected. The kitchen has really become a place for collaboration!

How does it feel to be in your new space?

It feels like home. It’s great to have a space where we can easily gather as a team, proudly bring in clients from around the world, host industry gatherings like Girl DevelopIt and DevOps meetups, and invite outside groups from places like universities to tour our office and learn more about technology careers. In our previous offices, we didn’t have as much space to easily provide a great experience for our visitors and our team. 

Some answers have been edited for length or clarity. 

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