At Squaremouth, Inc., 97 percent of employees say their workplace is great.



This review is based on 37 employee surveys, with a 90% confidence level and a margin of error of ± 3.10. It was published on Jun 6, 2017. 6877 Visitors

What Employees Say

Management is honest and ethical in its business practices.
Our facilities contribute to a good working environment.
Management is competent at running the business.
I am given the resources and equipment to do my job.
Management recognizes honest mistakes as part of doing business.

What They Do

We asked Squaremouth, Inc. to explain what they do. Here is what they had to say.

Squaremouth is an online company that compares travel insurance policies from every major provider in the United States. Using our comparison engine and customer reviews, travelers can search, compare and purchase travel insurance online.

About this Company

Website: Industry: Financial Services & Insurance
US Headquarters: St Petersburg, Florida, 33701 US Sites: 2
Major Locations: St. Petersburg, FL, Florida, 33701; Fort Wayne, IN, Indiana, 46802 US Employees: 39
Worldwide Revenues: $6.8 million Corporate Structure: Private
Founded: 2003

Squaremouth, Inc. has been awarded:

Best Small Workplaces 2017 (ranked 40)

Best Workplaces for Women 2015 (ranked 2)

Best Small Workplaces 2015 (ranked 20)

With news of the first Squaremouth pregnancy, employees, family and friends gathered at the CEO's house for a party.

Perks and Programs

We asked Squaremouth, Inc. to share a few programs they feel really capture what's unique about their workplace. Here is what they had to say.

  • Unlimited Paid Vacation: Squaremouth employees receive unlimited paid vacation, regardless of whether the days taken are personal, vacation, or illness. All Squaremouth employees must take a minimum of 10 days off each year.
  • Quarterly Profit Share: Squaremouth gives employees a bonus each quarter, intended to reward them for their performance and hard work. This bonus, based on the company’s quarterly profits, typically increases an employee’s salary by a few thousand dollars.
  • Mandatory Birthdays Off: Squaremouth employees receive a mandatory day off on their birthday, with a $200 bonus to be spent on beer. If an employee's birthday falls on a weekend, they can observe their day off on the nearest Friday or Monday.
  • Company-paid Trips: In March 2017, all Squaremouth employees were invited on an all-inclusive, company-paid cruise. The cruise was the first annual company trip. Moving forward, employees will vote on a destination.
  • Company Boat: In 2016, Squaremouth purchased a company boat for employees to take out at their leisure. After work, Squaremouth employees gather regularly for sunset cruises.
  • Local Event Tickets: Squaremouth's offices are right in the downtown areas of St. Petersburg, Florida, and Fort Wayne, Indiana. Both locations offer many local events, such as sports, theatre and concerts, and Squaremouth pays for all employees to attend.
  • Weekly Lunch and Happy Hour: Every Friday, Squaremouth buys lunch for all employees. At the end of the work day, employees gather in the office for company-provided beer and wine.
  • Snooker Table and Arcade Games: Squaremouth’s headquarters in St. Petersburg, Florida, features a regulation size Snooker table, a British style of billiards, as well as a cloud-based arcade game and a claw machine. Employees are welcome to challenge the CEO to a game of Snooker during lunch any day of the week.
  • Surprise Gifts for Employees: Not all perks are planned at Squaremouth. Past surprises include iPads and Apple Watches for all employees.
  • Continued Education: Squaremouth will cover the costs for employees to attend workshops and courses related to their careers.


$29,500 Average salary and additional cash compensation for Customer Service $86,000 Average salary and additional cash compensation for Developer
100% Match of employee’s 401(k)/403b contribution up to 4% of salary100% Company-paid health coverage for employees (for 64%)
Squaremouth employees have unlimited access to the company boat, and take weekly sunset cruises around Tampa Bay.


  • Telecommute option (67% use it)
  • Compressed work weeks (26% use it)
  • Subsidized On- or Off-site Fitness (100% have access)
  • Onsite Amenities (Coffee, arcade games, snooker table, couches and lounge chairs, beer, paid lunch every Friday, paid parking.)


100 days Job-protected maternity leave (including FMLA/STD) 60 days Fully-paid maternity leave (does not include personal vacation or paid time off)
40 days Job-protected paternity leave (including FMLA)15 days Fully-paid paternity leave (does not include personal vacation or paid time off)
40 days Job-protected parental leave for adoptive parents (including FMLA)15 days Fully-paid parental leave for adoptive parents (does not include personal vacation or paid time off)
*Employees are not required to use all their personal paid time off before taking parental leave. Not all employees are eligible for parental leave benefits.

Community and Environmental Impact

$10,000 Philanthropic donations in last year Yes Recycling program


  • Written policy prohibits discrimination based on (at a minimum) age, disability, race/ethnicity, religious beliefs, gender and sexual orientation
  • Formal programs (such as resource groups, mentorship, networking, or other affinity groups) support professional development for: Under-represented racial/ethnic minority groups; Women; Lesbian, gay, bisexual or transgender employees; Disabled employees; Speakers of English as a second language; Employees reentering the workforce
  • Non-birth parents in same-sex relationships can take parental leave
  • Medical care covers gender confirmation surgery

Leadership Diversity


Workforce Diversity

Squaremouth’s offices are completely open, with couches and lounge chairs, and no cubicles.


Christmas came early at Squaremouth in 2016. Employees decorated the office and held a Christmas party in November to surprise a colleague.

How to Get Hired

We asked Squaremouth, Inc. for some inside information on how to get hired at the organization. Here is what they had to say.

What key characteristics tell you a prospective employee will be a great fit for your company?

A great fit for Squaremouth’s culture is someone who can work autonomously, but is also willing to take feedback and work as part of a team. Squaremouth operates with complete company-wide transparency, so prospective employees must be comfortable receiving constructive criticism in an open environment. Great prospects will accept that criticism and use it to improve moving forward. At Squaremouth, employees can build their own jobs, and there is opportunity for rapid promotion. As a result, it’s important for a prospective employee to be highly motivated.

What can prospective employees do to get your attention?

Prospective employees should be able to prove they are motivated and interested in the job. It’s important that they come in having done plenty of research about Squaremouth, and they should have a list of questions prepared - both about the company and the specific job. Collaboration and communication are crucial for success at Squaremouth, so candidates also need to showcase their ability to work independently and within a team.

Are there any positions or types of candidates you are particularly focused on hiring in this coming year?

Customer service is our number one priority at Squaremouth. As we grow, we will continue to bolster our multi-award winning customer service department, as well as build our 24-hour claims team.

What should interested candidates do to find out more and get started?

Culture and transparency are extremely important to us. We spend a lot of time to make sure we hire the right people. Candidates who are comfortable working in a completely open environment will fit in well. To understand how we operate, candidates should visit our careers page and keep a constant pulse on us. We regularly produce articles and videos about our company culture and our values. 

hiring Outlook

15 Forecasted positions to fill in coming year 103 Average applicants per opening
1,138 Total job applicants 5% New hires by employee referrals
18% Openings filled by current employees 4 Recent graduates hired
3% Voluntary turnover for full-time employees 31% Voluntary turnover for part-time employees
* All figures refer to 12-month period prior to reporting, unless otherwise noted.

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