Steven Benna
Steven Benna
Marketing Manager
Jessica Burns
Jessica Burns
CEO
Robbie Burns
Robbie Burns
Product Development Manager
Cheri Cummings
Cheri Cummings
Claims Adjuster
Anna Gernandt
Anna Gernandt
Director of Design & UX
Nikki Gernandt
Nikki Gernandt
Front-End Developer
Aidan Harvey
Aidan Harvey
COO
Andrew Henning-Kolberg
Andrew Henning-Kolberg
Software Engineer
Dave Huffman
Dave Huffman
Software Engineer
Jeffrey Kimmel
Jeffrey Kimmel
Jr. Software Engineer
Angela Lambert
Angela Lambert
Call Center Manager
Macy McNaughton
Macy McNaughton
Office Manager
Megan Moncrief
Megan Moncrief
CMO
Mark Myers
Mark Myers
DevOps Engineer
Iryna Nikitenko
Iryna Nikitenko
Product Development Assistant
Andi Oates
Andi Oates
Director of Partner Integrations
Matt Outten
Matt Outten
CIO
Amanda Puff
Amanda Puff
Software Engineer
Chris Wenner
Chris Wenner
Project Manager / DevOps Engineer

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 Indeed.com and LinkedIn.com.

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.

Award-Winning Business Growth & Company Culture

Squaremouth Awards

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, squaremouth.com. Squaremouth.com is one of the...

August 19, 2020 — St. Petersburg-based travel insurance comparison site, Squaremouth, has been named one of Inc.’s 5000 Fastest-Growing Companies in America.  This is the 8th year in a row that Squaremouth has earned a spot on this list. According to Inc. Magazine, less than 2% of companies have made this list...