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Squaremouth rebounds after losing 90% of its business

Veronica Brezina



The Squaremouth team. Image provided.

St. Petersburg-based travel insurtech company Squaremouth has rebounded, after teetering on the brink of losing nearly all of its business activity with the onset of the pandemic. 

“Pre-pandemic, we were averaging hundreds of sales per day. By April 2020, our business came to a standstill, bottoming out at 12 sales one day,” CMO Megan Moncrief said in a statement. 

The pandemic marked the worst financial period the company has faced, dropping its business activity by more than 90% as travel became nearly nonexistent with restrictions placed on commercial flights and cruises. 

“We determined very early on we wouldn’t let anyone go, and everyone stayed at full salary,” Moncrief said. 

Every week, the company would remain transparent in sharing its financials during team calls, which painted an ominous and uncertain future. 

However, the narrative has flipped. As the pandemic has now subsided, Squaremouth is coming out on top, with sales projected to supersede 2019 by over 200%. 

Moncrief said the achievement can be attributed to several actions the company enacted, including applying for and 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 was going to bring a Silicon Valley-inspired design to the property by building treehouses connected by rope bridges and climbing walls. The sale of the HQ essentially was a break-even deal; however, the majority of Squaremouth’s employees work remotely and didn’t need a large physical space to function. 

For the company that heavily focuses on search engines and marketing, there was also a major pivot in the marketplace. Initially, the pandemic paused travel plans for many people and business travelers; however, it sparked interest in educating themselves about the protections of travel insurance. 

“One of our bigger initiatives was working with high-profile brands on marketing programs. The pandemic created a shift in search engines, 99% of people were searching about travel insurance and went to educational sites,” Moncrief said, explaining that Squaremouth teamed up with media partners such as Nerd Wallet and Money Insider to provide unbiased information.

“Working with these high-profile trusted brands got us through the pandemic,” she said. The move allowed Squaremouth to connect with a new demographic, younger customers who wanted a security net as restrictions were in place and later lifted. 

“There’s still a lot of pent-up demand and with inflation, people want to be protected,” Moncrief said.

Despite the pandemic ceasing, Squaremouth can gauge the interest people have in travel as it relates to the pandemic through a Covid search filter, which 34% of customers are still using.

There’s also a recent nationwide uptick in flight cancellations, which can lead to luggage becoming lost and other prone issues, which have also ultimately increased Squaremouth’s activity.  

Additionally, the company’s strong pre-pandemic revenue helped financially fuel it through the hardships and recover faster than others in the sector. 

“By going through this experience, it’s really brought everyone together in the long run,” Moncrief said. 

The company received recognition from Florida Trend and the International Best in Biz Awards for its culture and post-pandemic resiliency.

Today, Squaremouth still has a hybrid model and leases space inside Industrious, a co-working hub. It has a team of 50 employees, with 17 employees working remotely and in-person at the local office. Its engineers are based out of Indiana.

The company is hiring for positions in marketing, product development roles for candidates who understand insurance and the buildout product, and a customer service director and software developers out of Indiana.  

“From an insurance standpoint, we want to be on the forefront of getting ahead of concerns and provide creative benefits that aren’t always known,” Moncrief said, “and having underwriters who can include new language in policies is a big priority in the space.”  

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    Velva Lee Heraty

    October 15, 2022at12:01 am

    What a brilliant team of people. Years ago I remember reading that those companies that pull together, stay in the game, and adapt to circumstances during hard times will get out of the gate much sooner and with assured growth potential than those that receded and hid out. So here we are! Bravo!

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