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Pioneering in St. Pete since before it was cool.

Established in 2003 in Harvey’s home, Squaremouth 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.

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.

Company Overview

Company Name


Year Established


Number of Employees



Using our comparison engine and over 55,000 customer reviews, travelers can search, compare and purchase travel insurance online. All policies purchased through Squaremouth come with our Zero Complaint Guarantee. Established in 2003, Squaremouth has grown to over $21 million in annual sales in 2017. The multi-award winning company has been internationally recognized as one of the best customer service teams and one of the best places to work.

Awards & Accolades

Inc. Best Workplaces - 2017, 2018 Inc. 5000 - 2013, 2014, 2015, 2016, 2017 Tampa Bay Business Journal Fastest Growing Company - 2011, 2014, 2015, 2016, 2017 Tampa Bay Business Journal Best Places to Work - 2012, 2013, 2016 Tampa Bay Business Journal Coolest Office Spaces - 2014 American Business Awards (Customer Service) - 2014, Stevie Customer Service Department of the Year - 2014, 2016, 2017, 2018 Florida Trend Magazine - 18th Best Place to Work - 2015 Florida Trend Magazine - 26th Best Place to Work - 2016, 2017 Fortune No. 2 Best Workplaces for Women - 2015 Fortune No. 20 Best Small Workplace in the Nation - 2015 Fortune Best Workplaces in the Nation - 2017 CSS World Awards Customer Service Team of the Year - 2016 Entrepreneur Best Workplaces in the Country - 2017

Core values/mission statement

Fuck it up

It’s okay to fuck it up. It’s important to learn from your mistakes. Without learning from your mistakes, you are just fucking it up. It's how we react to, deal with, and learn from those mistakes that help make us incredible.

Everything we have done up to today is shit

Don’t misinterpret this, we are incredibly proud of what we have achieved so far. However, what is great today will very quickly become obsolete if our innovation stagnates. That happens to others, not us. Continuously improve, make it groovy. Don't over-engineer for the possibilities of the future. Don’t add needless features or complexity to our business or website. Find the elegant solution and we will stay way ahead of our competitors.

Love what you do, if you don’t, build yourself a new job

At Squaremouth, everyone is doing much more than the job they started with and most people are doing something different than what they interviewed for. Every employee has the ability to do anything they want to do. If your interests have changed and your creative spark needs igniting, go build yourself a new job!

It’s time you had a pay raise, prove you deserve it

Our raise process is a group effort, every employee has one vote. If you want a raise, make your pitch. If you get a majority vote, you got the raise! Repeat this cycle anytime. You will get your promotion or raise by impressing your colleagues every day, not your boss.

Company Leadership

Chris Harvey

Co-Founder and CEO

Chris Harvey is the co-founder and CEO of Squaremouth, a multi-award winning travel insurance comparison website, and Tin Leg, a travel insurance provider. Squaremouth launched its website,, in 2003 to help customers easily search, compare, and buy travel insurance. The company’s core value is to downsell, recommending the least expensive policy that matches each customer’s needs. Squaremouth focuses on customer service and employee development. The company has grown to $21 million in annual sales in 2017 and has consistently received national recognition for customer service, culture, and growth.

Matt Outten

Co-Founder and CIO

Matt Outten is the co-founder and CIO of Squaremouth. Matt has led the development of several internet startups in the online marketing and travel insurance industries. In 2004, he wrote the software for and built the website. was built on the foundation of providing exceptional customer service with a simple online experience. The company has grown to over $21 million in annual sales, with nearly 95% of customers purchasing policies online. Matt leads a team of senior developers in Fort Wayne, Indiana. Under his leadership, Squaremouth has been named one of the Best in Tech in Indiana by TechPoint.

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