Squaremouth puts hip workplace in downtown St. Petersburg

Tampa Bay Times
Published March 21, 2012

It's like preschool, but with beer.

It's like Survivor, but in an office.

It's like Expedia, but for travel insurance.

It's hard to describe St. Petersburg-based Squaremouth Inc. succinctly because it's different from most businesses in so many ways.

Its 10 employees have no phones or assigned desks. They work on the top floor of City Center, 100 Second Ave. S, barefoot and sitting criss-cross-apple-sauce on a white shag rug. They could opt to take their iPad2 out on the deck overlooking Al Lang Field or sit in one of the six sleek orange or green chairs with a fold-out desktop. Bud Light is always on tap at the keg next to the snooker table. (Snooker is like pool, but harder.)

The green couch is a favorite spot for naps, with blankets and pillows in the storage room.

If someone wants a raise, the whole company listens to their case and each person votes. Employees have unlimited paid vacation and have to take their birthdays off. Squaremouth's financials are in a Web document everyone can access.

"You can have a real funky workspace but if you're still doing things the same as everybody else, you're really no different. The reason we have glass walls, the reason everything is so open is because everything is transparent," said Chris Harvey, Squaremouth's founder. "When everybody votes on a raise, you don't just impress the boss, you have to impress everybody."

Nine-year-old Squaremouth moved downtown from St. Pete Beach in December. It posted $7.2 million in sales last year from its website, which offers 250 travel insurance products.

Harvey, 47, started the company as in his son's bedroom in 2003. That's the son whose mouth formed a perfect square when he cried as a baby. His nickname became the company's name in 2006 when Harvey wanted to distinguish it from other travel insurance websites. He started the company with a $250,000 loan against his home.

"Being less formal is certainly the culture in Silicon Valley at Google and places like that," said Edgar Schein, MIT professor of management and author of Organizational Culture and Leadership: A Dynamic View. "I know of very few organizations that will actually let a group make a decision that normally would be made by the boss. The positive would be it makes each player more valid in a group project. It requests a level of openness from the group and a willingness on the part of the boss to accept the group's judgment."

Transparency is big.

"If you're a person who wants to keep your head down and just do enough and not get yelled at, you'll be quickly found out in this kind of environment because it's so transparent," said Josh Walker, a product manager who brings new insurance providers to the site. He applied for a $10,000 raise 18 months ago but was turned down by the group.

"The embarrassment, you have to get over quickly. You have to show all your flaws as well as what works in your favor," Walker said. "Having people poke and prod at your flaws is an incredible way to grow."

He went for a raise again last week and his pay went from $41,200 to $51,200.

Everyone also got a vote on which of two locations the office would move to late last year. After looking at each one, they stood on a downtown sidewalk and had a show of hands. (A general consensus decided which beer would flow as well.)

Closing the generation gap

Americans spent nearly $1.8 billion on travel insurance and assistance services in 2010, up from $1.6 billion in 2008, according to Linda Kundell, a spokeswoman for the U.S. Travel Insurance Association. Packages cover different mishaps such as missed flights, needing a doctor in a foreign country or having to cancel that Disney Cruise because the kids have chicken pox.

The typical policy sold over Squaremouth ranges from $200 to $3,000 per trip. It takes a 25 percent cut from the products it sells but underwrites nothing. It's the middleman who helps buyers decide what options suit them best.

Other leading travel insurance sites include and

Harvey believes changing his company's name has made it more memorable but it wasn't an easy transition.

"Initially it hurt us on Google. We disappeared," he said. Sales dropped by $700,000 to $1 million in 2006 as marketing costs went from $24,000 to $100,000. Sales have climbed every year after that.

Harvey credits the company's blog that triggers links to other social media and an emphasis on customer service.

Each of the employees, no matter their job title, answers customer service calls that come through their computers. Helping that customer becomes their top priority.

Though Squaremouth screams "young and hip," most of its customers are 60 to 70 and Harvey wants them to feel comfortable, confident and appreciated. If several customers have the same question, then maybe a change should be made in a procedure or on the website.

"We may spend two hours talking about a three-line email," Harvey laughed.

Fitting the right pegs

Job applicants are warned up front the company has a distinctive corporate culture.

Beer on tap and unlimited vacation would be disastrous for someone who takes a mile when they are given an inch. But for hardworking, determined and happy employees, loose rules are empowering.

"I think people are more creative and productive when they are relaxed," Harvey said.

But can there be ill will if someone checks the books and finds out a colleague earns a much higher paycheck?

"I hope it creates ill will. Then they're going to come ask for a raise," Harvey said. Squaremouth gave everyone a 3 percent raise last year. Those wanting more can ask for a "raise meeting" at any time and make a presentation to colleagues.

"They almost don't need to make a presentation because it's based on what you're doing every day," he explained.

Squaremouth colleagues must explain their vote to everyone, including the employee in the hot seat. Harvey believes this prevents someone from voting "no" for petty reasons unrelated to work performance.

This peer approval mentality also limits printer use. Squaremouth has only one small, slow printer. If someone prints something, everyone else sees the walk of shame to retrieve it.

"Michele, what happens when we print?" Harvey recently asked operations manager MichelMichelle Kleinmetz. "Trees cry. Glares are sent across the room," she answered with a laugh, then added: "It seriously would take us over a year to go through one box of paper."

Katherine Snow Smith can be reached at (727) 893-8785 or