Jessica Burns

Chief Executive Officer

Jessica Burns, CEO

Jessica Burns is the Chief Executive Officer at Squaremouth. She oversees all of the company’s core projects and major initiatives and leads the company’s customer service department. Jessica has worked for Squaremouth for more than a decade starting in August 2010 as the company’s Accounts and Affiliate Manager. In her leadership position, she highly values the importance of the company’s people. She works closely with Squaremouth’s shareholders and executive team each week to identify new ideas and strategies that will boost Squaremouth’s company culture.

Jessica has been immersed in travel insurance for much of her life since her father founded the family business in 2003. Her intuition and knowledge of the industry is unparalleled, given her extensive understanding of the business itself and the challenges faced over almost 20 years. With this background, Jessica has a unique ability to contextualize the current travel insurance environment, which requires being responsive and adaptable amid unpredictable times.

Prior to taking over as CEO, Jessica spent 6 years as Squaremouth’s Director of Customer Service, where she used her extensive knowledge of the industry and the customer base to build and develop a multi-award-winning customer service team. Jessica works with the customer service management team on a daily basis to improve and maintain Squaremouth’s high customer satisfaction rating.

Megan Moncrief

Chief Marketing Officer

Megan Moncrief, CMO

Megan Moncrief is the Chief Marketing Officer at Squaremouth. She oversees all aspects of the company’s marketing initiatives, including media relations, affiliate partnerships, user experience, website content, and advertising.

Megan has a background representing companies with a focus on brand development, marketing, and PR. Megan has used these skills to bolster Squaremouth’s overall brand presence and establish a pipeline of international marketing partnerships.

Megan joined Squaremouth in October 2013. Before accomplishing her role as Squaremouth’s CMO, Megan held various positions within the company’s marketing department, including Marketing Manager and Director of Sales and Marketing.

Megan graduated from Florida State University with a major in Communications and Business. She serves as Squaremouth’s primary media representative, and has been featured as a travel insurance expert in major publications, such as Forbes, CNN, USA Today, and the New York Times.

Steven Benna

Lead Data Analyst

Steven Benna, Lead Data Analyst

Steven Benna is the Lead Data Analyst at Squaremouth. He is responsible for managing Squaremouth’s analytics and research team and studying data from thousands of policies purchased through This expertise allows him to identify real-time changes and trends within the travel insurance industry that inform our service offerings.

Steven looks at key data points every day to support the Squaremouth team, assist partners and media with their reporting, and help customers navigate the travel insurance market. He is also responsible for managing the company’s web content and various marketing projects, with a focus on SEO content and initiatives.

Steven joined Squaremouth in August 2016 as a Marketing Specialist. Prior to becoming Squaremouth’s Lead Data Analyst, he held roles as the company’s Content Director and Marketing Manager.

Steven studied Business Journalism at the University of Missouri and has a background in analytical reporting. Before joining the Squaremouth team, he was a journalist for Business Insider in New York.

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