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St. Pete travel insurance highlights its values through contests

Margie Manning



Squaremouth awarded a $10,000 check to contest winner Donelan Andrews.

Look for more contests in the next few months from the St. Petersburg travel insurance comparison company that just gave away $30,000 in prize money.

Squaremouth plans more campaigns that highlight customer service, transparency and other core values, said Jenna Hummer, director of public relations.

“It’s fun,” Hummer said about the company’s attention-grabbing contests. “We do travel insurance all day and we’re good at it, but we also like to shake things up and brighten someone’s day.”

Squaremouth just completed its first national contest, Pays to Read, designed to demonstrate the importance of completely reading an insurance policy.

Instead of announcing the contest publicly, Squaremouth hid the contest details in the fine print on the last page of a seven-page policy document.


The contest launched Feb. 11 and offered a $10,000 prize to the first person to respond by email.

The company expected it would be months before anyone caught on. But a Georgia schoolteacher, Donelan Andrews, responded less than a day after the launch and won the prize.

Squaremouth also gave an additional $5,000 to each of the schools where she teaches, and another $10,000 to Reading Is Fundamental, a nonprofit organization for children’s literacy.

In 2015, Squaremouth ran a local contest, awarding $1,000 to each of 20 outstanding customer service providers in St. Petersburg, with $10,000 for the overall winner.

Unlike most marketing strategies, the contests are not specifically designed to boost business at Squaremouth.

“The goal is to show how committed we are to being transparent and to reward people,” Hummer said. “Travel insurance as a product …  A very specific demographic buys it and for a very specific reason. Mostly they are people above the age of 45, taking more expensive trips and they want them to be covered. [The contests] give us visibility as a company and we love that, but it doesn’t translate into sales, because people don’t impulse buy travel insurance.”

There’ll be more contests this year, Hummer said.

Squaremouth, with $29 million in sales in 2018, has about 45 employees, including about 20 who do marketing and customer assurance at the St. Pete headquarters. There are about 22 workers in Fort Wayne, Ind. who deal with back-end technology, with the rest in customer service jobs working remotely.

The company bought a former church at 4355 Central Ave. in 2018 and is renovating the facility for a headquarters location. That work should be finished by the end of this year, Hummer said. In the meantime, the company is working out of a downtown St. Pete location.

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