Are You A Squaremouth Candidate?

Ideal candidates will have an intrinsic desire for personal growth and professional success.

They will be social, passionate about their work, laid-back and fun. They must be able to work with a lively group of overachievers. They will teach themselves, learn from others, and take ownership of their successes and challenges.

Current Job Openings
Squaremouth recognized as one of Inc. Magazine's Best Workplaces
Providing exceptional customer service has always been our number one priority. We believe this starts with creating the best possible work environment for our employees.

Why Work At Squaremouth?

We have received national recognition for our unique culture, nontraditional work environment and employee-centric benefits.

Our package of benefits is designed to reward hard work and promote a work-life balance. These have evolved to accommodate our growing company, with new perks being added by an employee vote. Benefits are based on department and tenure.

Unlimited Paid Vacation
Employees must take at least 10 days off per year, with no limit on sick or personal days.
401(k) Match
Squaremouth matches up to 4% of employee salaries for 401(k) contributions.
Quarterly Bonus
Squaremouth employees receive a quarterly bonus directly based on company profits.
Annual Salary Increase
Every employee receives an annual pay raise respective to the current Consumer Price Index.
Paid Medical Benefits
Squaremouth offers paid medical for employee and dependents as well as dental, vision, and life insurance.
Other Benefits
Squaremouth also offers dental, vision, and life insurance, and flexible spending accounts.
Work From Home
Squaremouth employees have the option to work from home full-time, regardless of department.
Optional Office Space
Squaremouth has offices in St. Petersburg, FL and Fort Wayne, IN for employees to use at their convenience.
Casual Work Environment
Squaremouth emphasizes a casual work environment with a beer fridge, arcade games, and no dress code.
Birthday Beer Bonus
Squaremouth employees enjoy a mandatory day off for their birthday with a $200 Birthday Beer Bonus.
Company Happy Hours
Employees get together in the office or at local establishments for company happy hours.
Paid Lunches
Squaremouth often buys lunch for employees at the office.

Squaremouth’s culture was built around complete transparency. We spoke with CNN Business to explain our company culture and our unique peer-voted raise and hiring process.

There is no stopgap. We rely on everyone having enough information and being intelligent enough that they will vote for an acceptable raise.

Group interviews and open salaries are core to Squaremouth’s culture. We sat down with Glassdoor to explain how we use group interviews to help us find the best fit for our company.

We are a very transparent company. For this reason, it is extremely important that anyone who joins us is comfortable with this type of transparency and open communication.

Award-Winning Company Culture

Everything we do at Squaremouth is in pursuit of our core goal to be the best place for anyone to buy travel insurance.

Navigating the Covid-19 Pandemic

Now, having survived the hardest part of the pandemic, Squaremouth is in an admirable position with sales projected to supersede pre-pandemic numbers by over 200 percent.

The company is also an outlier with a 50 percent female-led executive team. Having worked their way through the ranks of the multimillion-dollar company, the women in leadership positions feel acutely prepared for the shift their industry has experienced.

- TravelPulse

Squaremouth Core Values

Squaremouth's core values revolve around reputation over profits, “downselling”, and providing the best customer experience.

Strange is Good, Good is Bad

Different, unusual, weird. All are excellent traits for Squaremouth staff, however, if you are just good and don’t aspire to be incredible, go work somewhere else.

Love what you do, if you don’t, build yourself a new job

At Squaremouth, everyone is doing much more than the job they started with. Every employee has the ability to do anything they want to do. If your interests have changed and your creative spark needs igniting, go build yourself a new job!

Nothing to prove, nothing to lose, and nothing to hide

Egos can stay at the door. We deeply respect one another and recognize that everyone has different perspectives, strengths and opinions. No one has to hide what they think, believe or value.

Current Squaremouth Job Openings

Thank you for your interest in joining Squaremouth! Our current job openings are listed below.

We have been made aware of scammers posting fake Squaremouth jobs to gain personal information.
We will never ask for personal information via email during the interview process.

All of our active job openings are posted on this page. We also advertise our jobs on websites such as and

If you are interested in applying for a Squaremouth position, please do so below.

Many of our jobs receive a high amount of applications. If you do not see the job you are interested in, it has been closed.

Our team is constantly growing! Please check back in the future as we often post new opportunities to join us.

Squaremouth Culture Awards

October 12, 2022 — St. Petersburg-based travel insurtech company,, recently received recognition by Florida Trend and the International Best In Biz Awards, for their culture and post-pandemic resiliency. The awards come two years after the company’s business declined by over 90% as a result of Covid-19. Despite the downturn, Squaremouth pledged...

May 17, 2021 — Squaremouth has been recognized as one of the Best Workplaces in America by Inc. Magazine for the fifth consecutive year. The company – a travel insurance comparison site – rooted itself in two core goals when the company was founded in 2003: to be the best place to...

February 04, 2021 — One year since the Covid-19 outbreak halted the travel industry, travel insurance aggregator, Squaremouth, has earned its third international award for their customer service response to the pandemic. Who is Squaremouth? Squaremouth is the insurance software company behind travel insurance aggregator site, is one of the...