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  • <h1><br/><span class=Chris Harvey">

    Chris Harvey

    The entrepreneur behind Squaremouth.

    More about Chris
  • <span class=Growing


    The Squaremouth team laughs, drinks beer, and thrives together, growing from $1 million in sales in 2006 to $12 million in 2013.

  • <span class=Building the
    Best Place to Work">

    Building the
    Best Place to Work

    Harvey’s innovative work environment and team culture have been awarded Tampa Bay’s 2013 Overall Best Place to Work.


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  • <span class=Respected


    Chris has been featured as a travel insurance expert in most national publications.


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Done Differently

Travel insurance expert, CEO and Co-founder, Chris Harvey, has built a different sort of company in Squaremouth. His unusual hands-on (and shoes-off) approach finds him designing the company website and running marketing efforts, keeping him in direct contact with Squaremouth’s customers. Chris’ greatest passion is developing the best place for customers to buy travel insurance and the best workplace for his tight-knit team of employees – two lofty goals that are, in his eyes, inextricably tied together.

Learn More


Squaremouth is a website that allows travelers to instantly and easily access the most comprehensive travel insurance, trip cancellation, trip interruption and medical insurance packages on the market. Squaremouth’s product offerings, partnered with their unique Zero Complaint Guarantee, provide an unparalleled travel insurance experience.



Callout Link 1

“Squaremouth culture encourages perpetual growth, collaborative creativity, and achievement of excellence.” —Michelle Kleinmetz

Callout Link 2

“Squaremouth culture allows everyone to experiment, learn, grow and understand.” —Chris Harvey

Callout Link 3

“Culture means having respect for everyone’s ideas and opinions.” —Jessica Harvey

Callout Link 4

“Squaremouth culture is like awesome, but on steroids!” —Morgan Showman

Callout Link 5

“Culture is complete transparency and trust in everyone you work with.” —Sarah Byrne

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