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 perks and incentives have evolved over time, and are frequently re-evaluated to accommodate our growing company.

Generous PTO
Generous PTO package, plus sick days, personal days, and floating holidays.
401(k) Match
3% match of employee salaries for 401(k) contributions.
Performance Incentives
Employees are eligible for annual performance-based bonuses.
Work From Home
Employees are fully remote, with optional office space in select areas.
Medical and Other Benefits
Discounted medical benefits, plus dental, vision, and life insurance.
Birthday Bonus
Employees get a $200 Birthday Bonus during their birthday month.

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

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...