Squaremouth is headquartered in St. Petersburg, Florida, with offices in Fort Wayne, Indiana.

In 2019, Squaremouth surpassed $34 million in annual sales.

Squaremouth staff are regularly featured as industry experts in national publications, including The New York Times, CNN, and USA Today.


Squaremouth is a travel insurance comparison site that helps travelers search, compare, and buy travel insurance online. Squaremouth’s comparison engine and custom search filters allow travelers to find the most suitable policy for their trip. More than 300,000 travelers use Squaremouth to protect their trips each year.

At the core of Squaremouth’s customer service is the concept of “downselling”, an effort to save every customer money by finding and recommending the least expensive policy that matches their coverage needs. The company has stayed true to this goal, being recognized with multiple national and international customer service awards on an annual basis.

Squaremouth’s growth and culture have also been recognized on the national and local levels, including awards from Inc., Forbes, Fortune, and Entrepreneur.

Tin Leg Named “Best Travel Insurance for Seniors”

Tin Leg was named the best travel insurance provider for seniors by Forbes for its high medical coverage and competitive prices.

“Tin Leg often receives high marks for senior travel insurance. Tin Leg offers very competitive rates that can be more affordable than other companies.”

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Tin Leg – a Squaremouth Brand

Tin Leg was founded in 2014 by the experts at Squaremouth using years of experience working with travelers to understand what they want most in a travel insurance policy. Following the same mantra as its parent company, Tin Leg strives to save travelers money, and provide an unparalleled experience before, during and after their trip.

Understanding that the true test of an insurance company is their claims process, Tin Leg innovated a new type of claims experience – starting with an actual conversation with the claimant during an initial interview. By holding this call upfront, before sending forms and requesting documents, Tin Leg is able to set the customer’s expectations and save them time, resulting in a more positive experience.

Since its launch, Tin Leg has consistently been one of the top travel insurance providers on squaremouth.com. Tin Leg’s popularity stems from its strong reputation handling claims, high medical benefits, and competitive pricing.

Squaremouth has been named to the Inc. 5000 fastest-growing companies in America every year since 2013. This achievement is particularly remarkable, with less than 10% of companies nationwide being listed repeatedly.

Squaremouth has also been named one of the 50 fastest-growing companies in the Tampa Bay area by the Tampa Bay Business Journal eight times.

Innovation Leads to Steady Growth

Harvey’s approach to company growth has always been organic with no outside investors or sales goals. This allows technical innovation and exceptional customer service to generate revenue. As a result, Squaremouth’s annual sales have increased every year since 2006.

18.3% Increase in 2019

“We put a ton of energy into coming up with new ways to engage and motivate our employees.”

– Chris Harvey

Emphasizing Company Culture

Squaremouth’s company culture is built on transparency. From the office layouts to company financials and employee salaries – every aspect of Squaremouth is open for discussion and more-so, for change. This was Harvey’s vision from day-one, in an effort to establish trust and collaboration among staff and to create an environment where employees work for the respect of their colleagues, not just their boss.

Many of Squaremouth’s perks – such as unlimited paid vacation, a birthday beer bonus, and quarterly bonus profit-share – ring true of Silicon Valley startups. However, these have been around since the company was founded. Other benefits have been developed more recently, including taking a minimum of 10 vacation days, flexible hours, a company boat, and office facilities that include a full bar, daycare, gym and spa.

This innovative approach has garnered state and national recognition. Squaremouth has been named one of the best workplaces in the United States by Inc. Magazine and one of the best workplaces in Florida by Florida Trend, and has also received national recognition for its unique culture from Entrepreneur and Fortune, which named Squaremouth the #2 company on their list of the 100 Best Workplaces for Women.

Zero Complaint Guarantee

Every policy purchased through Squaremouth comes with a Zero Complaint Guarantee, the company’s promise to only sell policies from the most reputable, financially stable travel insurance providers in the industry. If a customer is unhappy with how their travel insurance provider is handling their claim, Squaremouth will step in and mediate on the customer’s behalf.

In the event a complaint is not handled to Squaremouth’s satisfaction, Squaremouth will remove that provider from the website and will no longer sell their policies.

Dedicated to Incredible Customer Service

Customer service has always been Squaremouth’s top priority. One of the company’s core values is “downselling”, an effort to save their customers money by finding the best policy for their trip at the lowest price. This approach has helped Squaremouth earn multiple international and national awards for exceptional customer service.

Squaremouth has earned a Stevie Award winner for Customer Service Department of the Year each year since 2015, and has won multiple gold international awards in the Customer Sales and Service World Awards. Squaremouth was also named the Most Customer Friendly Company in the International Best in Biz Awards, and was recognized with a Gold Magellan Award by Travel Weekly.

Squaremouth’s Biggest Investment to Date

After outgrowing its downtown penthouse office, Squaremouth purchased a nearly 60-year-old, 20,000-square-foot historic church to serve as the company’s headquarters. Squaremouth began construction in early 2018 to transform the building into a state-of-the-art workspace.

The purchase of the church gives Squaremouth the freedom to create an office that accommodates its growth, with suggestions coming directly from employees. The restoration plan includes tree houses, a suspension bridge, a gym and spa, daycare, a bar, and nap pods.

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“Our greatest investment has always been in our employees. We ask everyone to contribute their ideas, and we discuss construction plans during our weekly company meetings.

– Chris Harvey

Squaremouth Rewards Local Employees for Their Customer Service

In 2015, Squaremouth’s Florida employees in St. Petersburg, Florida selected 20 local individuals to reward based on their outstanding dedication to customer service. Each winner was surprised with $1,000 in cash; one grand prize winner received an additional $10,000.

The Thank You Campaign was Squaremouth’s way of recognizing individuals who have chosen to go above and beyond for their customers every day.

Squaremouth’s Campaigns

Squaremouth Awards $30,000 in Top-Secret Policy Reading Contest

In an effort to highlight the importance of reading policy documents, Squaremouth launched Pays to Read in February 2019, a secret contest that rewarded $10,000 to the first individual to read their policy from start to finish. Much to Squaremouth’s surprise, the contest – which was slated to last one year – was won in just 23 hours by Donelan Andrews, a consumer economics teacher from Georgia.

At the contest’s conclusion, Squaremouth also donated an additional $10,000 to Reading Is Fundamental, a children’s literacy charity. Inspired by Donelan’s commitment to her schools, Squaremouth made a surprise donation of $5,000 to each of the two high schools she teaches at in Georgia – Upson-Lee High School and Lamar County High School.

Chris Harvey is the original founder and former CEO of Squaremouth, the software company behind travel insurance comparison site, squaremouth.com, and travel insurance company, Tin Leg.

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