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Hello Chris

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Nothing Square About It

Chris Harvey is the CEO and Co-Founder of Squaremouth, the software company behind travel insurance comparison site

With a Zero Complaint Guarantee and the most comprehensive list of travel insurance products (according to The New York Times), Squaremouth’s growth should come as no surprise. But while customers may sense there is something different about this company, few realize how much of its success can be attributed to the unique culture of the business behind their computer screen.

Visitors to the company’s St. Petersburg, Florida headquarters are immediately exposed to Squaremouth’s core philosophy. Open space takes the place of cubicles, and windows replace walls, but nothing about Squaremouth’s design is accidental. This same transparency exists virtually everywhere in the company. Employees know each other’s salaries and have access to the company’s financials, even customers are able to see Squaremouth’s current sales on the website’s homepage. With perks including  an office-wide sound system controlled by each employee, no assigned desks, a snooker table, and a hangover carpet, the perks of Squaremouth are those typically reserved for the Silicon Valley giants.

But how does this casual atmosphere impact productivity?

A Different Kind of Company,
A Different Kind of CEO

With a workplace regarded as “preschool, but with beer,” by the Tampa Bay Times, Squaremouth’s tight-knit team of employees enjoy spending their days in the company’s waterfront office in downtown St. Petersburg. Chris spends most of his time focused on marketing initiatives and better serving his customers.

Chris’ travel insurance expertise stems from a lifetime in the industry. In 1998 Chris moved from the UK to the United States to join an insurance administration software developer. He later became a partner with a financial software company that developed billing engines for insurance carriers in 2000.

In 2001, Chris began developing the concept that would eventually become Squaremouth. Two years later he launched a comparison engine for travel insurance, which he called In 2006, the company changed its name to

Chris makes frequent contributions as a travel insurance expert for major media outlets, radio shows, and news publications, including the New York Times, LA Times, CNN, USA Today, Bloomberg BusinessWeek, Forbes, MSNBC and the Wall Street Journal.

Unlimited vacation, beer on tap, and a napping couch might sound like the fast track to financial ruin, but for the right employees, Chris has found that this atmosphere encourages creativity and productivity. In this workplace, every employee’s ideas matter, from suggestions for better customer service to deciding whether a fellow employee deserves a raise. This inherent teamwork has contributed to Squaremouth’s growth to over $19 million in annual sales.

Squaremouth is regarded as one of the most innovative companies in its field and is the fastest growing website of its kind in the United States.

For media requests or more information about Squaremouth,

Contact Chris