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Join Our Team

Why Join Us?

At Trailstone, our core mission is centered around serving others to enrich their lives.

As an Independent Insurance Agency, we prioritize our clients and employees by partnering with over 40 carriers to provide the best coverage options and prices available. Our dedicated agents go above and beyond to ensure their clients are informed about their coverages by approaching their work with the heart of a teacher.

Why join our team?

Joining our team means becoming part of a supportive community. We are committed to helping you achieve your full potential.

See below for a brief overview of the primary positions we hire for and click on Apply Now to be taken to the full job postings and to see what positions we are currently hiring for.

Apply Now

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Job Opportunities

Entry Level Customer Service Specialist

Personal Lines Account Managers

Apply Now

What our agents have to say about working with Trailstone Insurance Group

Work from home but feels like family!

I can honestly say I’ve never worked anywhere that had as much support, encouragement, and training as what Trailstone offers. I came to Trailstone knowing zilch about insurance except my own bad experiences. But I did have a desire to change the way people saw insurance industry and Trailstone is changing the way insurance is done. From the treatment of its employees, to the way we serve our clients, to the mindset of having the heart of a teacher, everything about Trailstone is about improving the customer experience through knowledge and education. Although most of us work in different cities and states, and very few go to the actual office, it somehow still feels like family! Hardest part is the learning curve at the beginning, but if you can stick it out, it is well worth your time investment! Trailstone has everything you need and more, to be successful, you just have to utilize it. Almost a year in, and I can’t see myself going anywhere else!

Supportive Culture

I started working at Trailstone almost two years ago with no experience in the insurance industry. I am blessed to be apart of a team that has helped me to grow and thrive in this industry. Management has an open door policy and has provided a level of support that I have never experienced in any past career or job. The agency is people focused – do right by others, whether that be co-workers or clients.

Trailstone is full of high achievers who value people. In order to thrive here you must value serving others well and come to work eager to be there. Being an agent is not an easy role and is for people who want to put in the work to reap the rewards but you do have an entire team to lean into. With all that said, I can’t imagine being an agent for any other agency.

Fast-paced & rewarding with great structure and support

Trailstone sets you up for success, but it is up to you to put in the work to be successful. I joined Trailstone with no insurance experience. Management and ownership have not only created amazing systems to help train new hires, they are there to walk you through the process step by step until you’ve mastered it. Everyone – from the top down – is patient and extremely helpful, and the overall company culture is truly the best I’ve ever been a part of.

The tools and automation that have been painstakingly perfected over the years are invaluable, and make the job so much easier. Still, you must put in the effort to learn and to master the process. If you’re willing to do that, the sky is the limit. Once you’re established, the work-life balance is unparalleled. This job has enabled me to do things I never thought I’d be able to do and go on adventures that we otherwise wouldn’t have been able to go on – all while still supporting my family and being fully present in their lives.

The bottom line is you get out what you put in. If you put in the effort, you will reap the rewards.