At Ashland Insurance, we believe our greatest strength lies in the incredible individuals who make up our team. We’ve been building a team of top-notch professionals who are passionate about serving our community. By bringing together talented individuals with diverse backgrounds and experiences, we can provide the best possible insurance solutions for our clients.
That’s why we’re so excited to shine a spotlight on our newest team member, Charles Chesnut. He brings a unique background and a fresh perspective (from both sides of the lens!). You’ll see pretty quickly why he’s such a valuable addition – not just for his insurance expertise, but for the genuine person he is.
A Journey to Service
Charles Chesnut’s journey into the world of insurance might just surprise you. For nearly 30 years, he was a talented commercial photographer based out of Portland, Oregon, capturing moments and crafting visual stories. You could say he has taken every Visual Aspect into consideration throughout his career.
But life has a way of leading us to new horizons, now doesn’t it? As recent empty nesters with two adult children living and thriving on their own, Charles and his wife, Susan, were eager to explore a new chapter. After a year-long search for the perfect Pacific Northwest community, they relocated to our stunning southern Oregon in 2022.
This significant life change sparked a career shift too. In 2020, Charles began seeking new professional options, aiming for an opportunity that would allow him and Susan to live just about anywhere, stay closer to home, and truly focus on a more rural lifestyle. With the right folks around him to mentor a bit of his journey to find the space and place that would be most fitting, Charles was introduced to the world of working in insurance.
Through this curious inquiry, Charles’ journey led him to a fulfilling new path: assisting seniors in navigating the complexities of Medicare Insurance Plans. Despite being a significant career shift, he quickly discovered the genuine satisfaction of connecting with clients, learning their personal stories, and providing clarity and peace-of-mind in the often-confusing world of Medicare. Finding his connection in this service wasn’t hard to come by either. In being the youngest of five in his own family, he was surrounded by folks that just happened to err on the older-than-him side of the spectrum.
“I feel like my clients are aunts and uncles…that I get to help out. [T]they have sort of a place in my mind that is not just a source of income for me, but they’re actual genuine folks that I care about and I want to help make sure that they’re comfortable and they’re safe and that they’re insurance is doing what it needs to do”
From Independence to Teamwork
With guidance from some great folks out of Seattle, Charles Chesnut began his professional journey independently. Now, after four years as an independent Medicare Insurance Producer, there’s just something special about being part of a local community, isn’t there? The desire to join a local team and to be able to offer a wider range of services to his clients is what ultimately led him to Ashland Insurance.
He values the collaborative environment of a well-respected, community-focused company like ours. This new chapter allows him to serve a wider range of individuals with access to even more diverse insurance options, including Individual and Group Health plans.
“It’s nice to be part of a team,” Charles explains, “and part of an opportunity for providing other insurance lines to my clients and their recommendations.”
Since officially joining our team on May 1st, Charles has already made a significant impact. His arrival couldn’t have been more perfectly timed either, coinciding just as a long-time Medicare and health insurance specialist retired. Talk about the universe aligning!
Making a Difference
Charles’ dedication to his clients goes so much deeper than simply finding the right policy. He takes immense pride in helping them truly understand their options and, as he often does, save them a significant amount of money.
“There are many instances where we’re able to save– especially if it’s a couple, it could be as much as $800, or $1,000 a month,” he says. “When they’re on a fixed income and they’re not sure where they’re going to need to compromise…And all of a sudden they have another $800 in their bank account every month…they’re ecstatic about that.” Imagine the peace of mind that brings.
Beyond the financial benefits, Charles truly cherishes the personal connections he forms. He recently shared a story about a client who was moving back to California. She specifically called him with a question, but also to express her heartfelt thanks for his support and care during her time as his client. Now that’s what we call making a lasting impact!
Life Beyond the Office
When Charles isn’t busy helping clients, you’ll find him truly enjoying his five-acre property in Talent, Oregon, where he and Susan currently reside. He and his wife are busy transforming their land into their own personal oasis, complete with a thriving garden and plenty of space for their beloved dog to play. Charles also shares his passion for various outdoor adventures, as he’s an enthusiastic hiker, fisherman, skier, and woodworker.
You know how important community is to us, and it’s clearly important to Charles too! He’s actively involved in the Ashland Rotary Club, dedicating his time to local service projects. This includes their incredible community garden, where they raise vegetables and donate them to the Ashland Food Bank every summer. In fact, last year alone, they donated over 5,000 pounds of fresh produce! Charles also occasionally participates in international NGO initiatives.
When he’s not tending to the land or helping his community, he cherishes spending quality time with his family.
Charles Chesnut and His Future with Ashland Insurance
Charles Chesnut ‘s unique blend of extensive experience, genuine compassion, and deep community spirit makes him an incredible addition to Ashland Insurance. We’re confident that his dedication to serving others will make a wonderfully positive impact on our clients and the community as a whole.
Welcome to the team, Charles!
Ready to connect? Reach out!
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