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St. Pete insurtech firm names new CEO

Veronica Brezina



Unsplash image by Francesca Tirico.

St. Petersburg-based travel insurtech company Squaremouth, which rebounded after the pandemic caused it to lose nearly all of its business activity, has a new leader at the helm. 

The bootstrapped insuretch company has appointed Rupa Mehta as its new CEO, replacing Jessica Burns, who worked at Squaremouth for over a decade, serving in various executive positions. 

Burns, who is the daughter of Squaremouth’s founder, Chris Harvey, is retiring for family reasons.

The announcement did not disclose Mehta’s start date for the new role. 

The Squaremouth team and former CEO Jessica Burns (center). Image provided.

 Mehta has 16 years of leadership experience under her belt. She most recently led and grew marketplace businesses with Angi and Groupon, global leaders in the advertisement and directory platforms space.

“Squaremouth’s impressive product capabilities and customer-led approach make them uniquely positioned to capture tremendous growth opportunities within the travel space,” Mehta said in Squaremouth’s Tuesday announcement. 

Rupa Mehta, the new CEO of Squaremouth. LinkedIn image.

Squaremouth, founded in 2003, claims to have the largest portfolio of travel insurance providers and products in the U.S. market, with over 3 million travelers insured. 

Mehta has led groups “in similar entrepreneurial cultures,” according to Squaremouth. She will be responsible for guiding and overseeing the company’s strategic initiatives and growth opportunities.

“We believe comparison shopping will continue to guide consumer behavior. Our breadth of insurance offerings, commitment to a seamless user experience, and award-winning support have placed us at the forefront of our industry,” Matt Outten, CIO and co-founder of Squaremouth, said in a prepared statement. “Rupa’s proven experience in marketplace environments makes her an exciting and complementary addition to our leadership team. As we celebrate 20 years in business, we look forward to continued success under her guidance.”

The change in the leadership makeup comes after the company climbed its way out of the financial woes brought forth by the pandemic by receiving a PPP (Paycheck Protection Program) loan, halting spending funds on non-critical items, and selling its HQ building, also known as “the church property,” which encompasses an entire city block on Central Avenue. 

Squaremouth still has a hybrid model and leases space inside Industrious, a co-working hub.

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