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Squaremouth outgrows downtown, moves to historic Central Avenue church

Megan Holmes



Signing a waiver probably isn’t on most software companies’ onboarding checklists. But most software company CEOs probably don’t have the vision of Chris Harvey either.

Harvey and his award-winning company, Squaremouth just moved in to their new digs – a 20,000+ square foot historic church on the west side of Central Avenue – purchased for $1.4 million. Among the future features of the office? A series of treehouses with rope bridges, climbing walls and fire poles as access and exit points. Or – just take the stairs, of course.

Squaremouth has been pioneering in St. Pete since before it was cool. Established in 2003 in Harvey’s home, the company lived in various locations on St. Pete Beach until the hustle and bustle of St. Pete’s business and arts renaissance brought it downtown. The travel insurance comparison site was an early addition the downtown scene when it took over the top floor of the City Center building in 2012.

Situated at 100 2nd Ave. S., the penthouse office provided sweeping waterfront vistas, flowing beer and nap couches. That same year, Squaremouth posted $7.2 million in sales.

The main “office” was once the church’s sanctuary. Here, Harvey plans to build treehouse meeting rooms, connected by rope bridges.

Fast forward to 2018, and Squaremouth has taken its pioneering west of 34th Street – past the boundaries of the Grand Central and Warehouse Arts Districts – and into its historic church home at 4355 Central Avenue. The company now exceeds $18 million in annual sales and has gained national recognition for its “strange” and vibrant culture, as well as its growth. It has been named an Inc. 5000 fastest-growing company each year since 2013, and was named one of the best workplaces in the nation by Inc. in 2017 and 2018.

So why leave the cozy City Center office? Recognition and growth bring their own challenges. Namely, a shortage of nap couches – and desks.

Squaremouth’s growth outpaced its downtown office space. At first, the logistical challenges could be managed. The company rented a separate floor for a time, in an effort to meet space needs. Customer service was housed there. In a Tetris-like fashion, Squaremouth employees were mandated one work-from-home day per week.

Desks were juggled, calendars were formalized and employees got to work in their pajamas. But it just wasn’t right, according to Megan Moncrief, the company’s Director of Marketing & Sales. “Even that felt like too much separation for us,” she said. “We’re so collaborative. As a small company, we just didn’t like being separate. So we found a bigger space.”

Squaremouth’s new home at 4355 Central Ave, a historic church. Photo provided by Squaremouth.

More like the biggest space they could find. Squaremouth’s new headquarters takes up an entire city block, and sits on a 72,000-square-foot property, according to Moncrief.

If growth continues as it has for the last five years, they’ll need the space. When Moncrief started at Squaremouth five years ago, there were only five employees in the office. Now there are 37.

Squaremouth not only aggregates outside travel insurance quotes, it also provides its own travel insurance product – Tin Leg – alongside those competitors. Tin Leg also happens to be its top seller, and it provides a novel direction for the Squaremouth team to plant a flag and chase sales. The “software” company has already brought customer service, marketing, claims adjustment, design and development in house as well.

In the new space, Squaremouth will have ample space to hire, and enough leftover to build out Harvey’s vision for a public coffee shop and co-working space in what is currently a courtyard and recreation center. But it may be a few years until that concept is fully fleshed out. According to Moncrief, it will likely be a year before Squaremouth employees see drastic improvements to their workspace – and probably two until the coffee shop and co-working space is completed.

Right now, the company is focused on the groundwork (literally; the foundation needed some work). Next will be the roof. There have been more than a few bumps along the way bringing the 1940s church up to code. The occupancy standards had to be changed from a church to a business, the roof needs to be completely redone. And then there are the stained glass windows in the “old” sanctuary, the main office space. They’ll go too. Hopefully, they’ll be donated to Haiti, along with the church’s pews.

“Even when we came in to see it when it was still full of pews, we were like whoa, this is going to be awesome. It’s just going to take a minute,” said Moncrief. “Chris has such good eye, he’s going to make it look super modern. I think it’s going to look really cool juxtaposition. You’re going to know it’s a church, but it won’t necessarily feel like it.”


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Employees moved into the space in April, they currently work along stained glass windows, original to the church.

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