Customer Reviews

Working with Nathaniel and Bethany has saved our small business a lot of money and made dealing with insurance so much easier. They are always quick to help, responsive, and happy to answer any questions we have. If you’re considering switching insurance providers, you won’t regret giving them a try!

I can’t say enough about the outstanding service I received from Bethany who is a Commercial Account Executive at UPSIDE. Even though our company is not a client of hers, she took the time to help me troubleshoot a complicated issue with our Workers’ Compensation insurance. She listened carefully, understood the problem, and guided me on how to get my policy corrected with my current provider. Her professionalism, expertise, and genuine willingness to help—without any obligation—truly impressed me. It’s rare to find someone in this industry who goes above and beyond simply to help a business owner succeed. If you’re looking for an insurance partner who is knowledgeable, responsive, and genuinely cares about their clients, I highly recommend Bethany Gilmore and the UPSIDE team. If I ever switch companies, I’ll be calling UPSIDE first!

Upside Insurance Services — professional, kind, and focused on doing what’s best for their clients. The team is welcoming, knowledgeable, and incredibly easy to work with. They bring a personal touch that’s nice to work with, and it’s clear they genuinely care about the people they serve. Highly recommend if you’re looking for an insurance company you can trust.

Our family have worked with the Upside Insurance team for years and it has been nothing short of outstanding! Megan Cooper on their team has been such a wonderful support system and is always responsive and helpful when we have questions.

Upside Insurance is Awesome to work with! They will make sure your coverages are appropriate and competitively priced. Their Customer Service is one of their best qualities (And the People are great too!)

Upside Insurance has been an exceptional partner for my business since I moved from Canada to the US in 2020. Navigating the differences between operating in the two countries was daunting, but Upside Insurance, introduced to me through a mutual connection, made the transition seamless. They quickly had me fully covered for all my business needs, including workers' comp, just in time for my move into a new warehouse space. Over the past four years, they have consistently demonstrated their expertise, always being attentive and timely in their responses. Upside Insurance continually works to ensure I have the best coverage at the most competitive rates, and they have a remarkable ability to anticipate my needs as a small business owner. They are thorough, responsive, and never keep you waiting. I highly recommend them to any small business looking for a reliable and knowledgeable insurance agency.

Megan really goes above and beyond helping us with our insurance. Not only did she help us save a ton of money when we switched to Upside, but Megan tracked down thousands of dollars we were charged erroneously and helped get it back!! We will be clients for life.

Upside Insurance is my go to insurance group for my business owner clients. They are dedicated to personal service and look out for the best interest of their clients. If you want honesty and personal, white glove service give them a call.

I recently had the pleasure of working with Colin Vogel from Upside Insurance, and I couldn't be more impressed with the experience. We had only intended for Upside to handle one policy, but I quickly realized it was best to have their team handle all of our insurance needs. Colin was always prompt in his responses, whether it was answering my questions via email or scheduling follow-up calls for more detailed discussions. Definitely worth an exploratory call - I'm glad I made it.