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Why a St. Pete startup has scrapped its Silicon Valley-esque HQ dreams to go fully remote


Squaremouth new headquarters
Squaremouth recently sold its historic headquarters.
Courtesy photo

St. Petersburg-based Squaremouth once had dreams of having a tech headquarters rivaling the likes of Google and Facebook. Its former CEO, Chris Harvey, said he wanted the startup digs to have climbing walls, fire poles in place of stairs, and treehouses galore. 

But that dream is officially done with the sale of the company's historic church-turned-headquarters. 

"Whenever we're thinking about having everyone together, the office space was a real big thing," Squaremouth CEO Jessica Burns said. "But as we progress, we realized that's not what the employees wanted. We wanted everyone to have that work-life balance, and that was more important to have that than a cool office space."

Jessica Burns
Jessica Burns, CEO of Squaremouth
Ashlee Hamon Photography, INC

The travel insurance technology company recently sold its historic headquarters, which took up an entire block in St. Petersburg, for $1.86 million. The company kept its downtown office space, and when that lease ends at the end of the year, it will move to a smaller area for collaboration and social spaces. While the company is remote, Burns said nearly 100% of the 35 employees wanted "the option" to come into the office.

"I think we are doing things that work for us; I don't think we have much of an opinion on what others are doing, and it's tough to dictate what will or won’t work at other companies," Burns said. "Definitely for us is how our employees are responding to these changes. I think people do enjoy being in the office, and if we had one where everyone wanted to get together, that might have driven our decision."

Squaremouth
A look at Squaremouth's downtown office space.
Squaremouth

Downsizing headquarters spaces is not a particularly unusual move in the tech startup world, but it contrasts with the vast majority of companies in the Tampa Bay region. Many tech-focused local giants, including ReliaQuest and ConnectWise, have not only stuck to a hybrid format but made significant investments in new office spaces.

"There are some things where there's a camaraderie and efficiency," Brian Murphy, CEO of ReliaQuest, said in a previous interview with the Tampa Bay Business Journal. "I think you won’t see it all go back on-premise, but for the leadership academy and other things, they need to be in person for engagement reasons."

But Squaremouth has tried to stay ahead of the game for office protocol. It has long had an unlimited time-off policy, and pre-pandemic, the company had unassigned office desks that many companies are now incorporating to save office space.

"We were ahead of the game with things like unlimited time off, so when that started to become the norm, we thought, 'What's next, what's new?'" Burns said. "Companies have proven things can function extremely well remote, and that's absolutely the way forward."

Engagement and maintaining culture is the oft-most cited reasoning for keeping a sizeable in-person presence. Burns said Squaremouth is still working through the best practices to maintain a sense of culture and acknowledges there will be an in-person component, even if it's not in a formal office setting.

"One of the things that makes Squaremouth unique is the culture we have fosters friendship," she said. "Lots of our meetings do include social time — they chat about what's going on in their lives outside of the meeting topics. We did do a happy hour and monthly gathering, but with [Covid-19] cases rising ... we hope when things settle down, that will be our goal."


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