Are you a Squaremouth Candidate?

Ideal candidates will have an intrinsic desire for personal growth and professional success. They will be sociable, 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. The organizational structure of Squaremouth is flat, so candidates must be able to multi-task and work autonomously in a constantly changing environment. Because there is no traditional hierarchy, everyone works as part of a team. There is no “typical day” in this office, so it is best-suited to those who thrive in the absence of structure and routine.

Squaremouth is a fast-paced and exciting company which strongly encourages employee input and ideas

Most of what we do is a group effort, including interviews and pay raises. At any time, employees can request pay raises, which are determined by a majority vote from their co-workers. With this uniqueness comes the dedication to the Squaremouth Way, best described as the constant pursuit of perfection, unfettered attention to detail, incredible customer service and a burning desire to do things better tomorrow. A vital part of our commitment to incredible customer service depends upon every Squaremouth employee, including the CEO, spending time each day working directly with customers.

Why Work at Squaremouth?

Unlimited Paid Vacation

Employees have at least 10 paid days off, with no limit on vacation or sick time.

401(k) Match

Squaremouth matches up to 4% of employee salary contributions.

Quarterly Bonus

Squaremouth employees receive a share of quarterly profits.

Medical Benefits

Squaremouth offers medical, dental, vision, life insurance and flexible spending accounts.

Rapid Promotion

Fast-paced environment with opportunity for quick growth and promotion.

Birthday Beer Bonus

Enjoy a mandatory birthday off with a $200 bonus to be spent on beer.

Annual CPI Increase

Every employee receives an annual salary increase respective to the current CPI.

Unexpected Surprises

Some perks aren’t planned! Past surprises include a new iPad and Apple Watch for every employee.

“We are a highly customer-focused company, and we’ve always believed that in order for us to provide the best customer service, we have to provide the best work environment.”

– Squaremouth Co-Founder and CEO, Chris Harvey

Squaremouth Culture in the News

Squaremouth Named No. 2 Workplace for Women in the Nation


Fortune Magazine and Great Place to Work named Squaremouth No. 2 on the 2015 list of 100 Best Workplaces for Women. Squaremouth and the other top companies were selected for promoting equal and inclusive environments for both genders. “Fairness is inherent to our operations. Our culture is nontraditional in that we are extremely transparent and collaborative, which naturally promotes equality,” says CEO Chris Harvey. “There are no secrets, and decision-making is a group effort.”

Read more

Squaremouth’s unique, award-winning offices and culture are regularly featured in the news

  • Bay News 9

    Squaremouth’s Award-Winning Culture Featured by Bay News 9

    Squaremouth was named one of the best workplaces in the country in 2017 for its one-of-a-kind culture and employee perks. Local TV station Bay News 9 visited Squaremouth’s St. Petersburg office to see the company’s unique work environment first-hand. “The list of perks for employees of one downtown St. Petersburg company might seem beyond belief. The workplace includes a waterfront view, a pool table, games and an open bar, and employees can make use of two company boats and unlimited paid vacation.” June 8, 2017 Read more
  • Squaremouth is One of Tampa Bay’s Best Places to Work

    Squaremouth is One of Tampa Bay’s Best Places to Work

    The Tampa Bay Business Journal named Squaremouth one of the Best Places to Work in Tampa Bay in 2016. Its unique roster of benefits sets Squaremouth apart as a great place to work, but it is the company’s culture of transparency and collaboration that makes it a great place to grow and succeed, according to employees.
    "Squaremouth's culture empowers employees,” said Project Management Director Megan Moncrief. “I have never felt so in control of my own career and success." April 27, 2016
    Read more
  • Business Observer Features Squaremouth's Unique Raise Approach

    Business Observer Features Squaremouth’s Unique Raise Approach

    The raise policy is one of several unique culture-building features at Squaremouth, co-founded in 2001 by insurance software entrepreneur Chris Harvey.

    Group decision raises, says Harvey, are good for employees and the company because they create a productive and transparent business that complements the Squaremouth Way. . . Employees feed off each other in work ethic and productivity, and the transparent environment means employees self-police and know who’s doing raise-worthy work.
    February 5, 2016
    Read more
  • Open-Pay Policy Featured in Wall Street Journal

    Squaremouth’s Open-Pay Policy Featured in Wall Street Journal

    The Wall Street Journal featured Squaremouth’s unique, transparent workplace culture, where employees vote on raises requested by their colleagues.
    “Squaremouth, a travel-insurance comparison website with an open-pay policy, goes an extra step by allowing its 37 employees to vote on raises requested by colleagues on their teams. Employees make their pitch, and a majority vote is required for approval. Bosses vote, too, giving reasons for their vote. Salaries for comparable jobs elsewhere are part of the discussion. Two of 23 raise requests have been turned down since the company started the practice in 2010.”
    January 12, 2016
    Read more
  • 2015 Best Small Workplaces by Fortune

    Squaremouth Lands on National List of Best Small Workplaces

    Squaremouth has been named No. 20 on the 2015 list of Best Small Workplaces by Fortune and Great Place to Work. While Squaremouth's offbeat workplace and unique perks make it appealing, it is the strong camaraderie among colleagues that most staff cite as the best part of working at the company. October 21, 2015 Read more
  • inc5000_color_stacked

    One of America’s Fastest Growing Companies

    Squaremouth has been recognized as one of the fastest growing companies in the nation by Inc. Magazine for the past four years. The Tampa Bay Business Journal has named Squaremouth one of the 50 fastest growing companies for five years running.
    “At our core, we are a software company, so we constantly look for new ways to improve all aspects of our business, from our website to our customer service,” says CEO Chris Harvey. “We also believe that to be an innovative company, you also have to be an innovative employer.”
    Read more

Current Openings