Our Story
Oakley Insurance Group celebrates its 10th Anniversary in December, 2025!
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Oakley Insurance Group was born out of the frustration of not being able to offer clients options. Our owner Shawn, has been in the insurance industry since the early 1990's and has been dedicated to serving her community by way of insurance protection. After working as a captive agent, someone who is bound by one insurance company to sell only their product, she was unhappy with being captive. In the late fourth quarter of 2015, Oakley Insurance Group was born, named after a street Shawn lived on in Chicago, Illinois.
The Vision for Oakley Insurance Group is to put clients coverage needs above all else, including premium or commission. Our agency doesn't chase commission, and our clients don't chase premiums because we all value the same thing - true protection if some of the worst in life happens. We achieve this vision through one-on-one client education, making sure each person who choses a policy from us knows what they're buying, why their buying it, and how it works if they need to utilize the coverage they've purchased. We have team members who closely monitor the insurance industry to identify trends that may affect our clients. We then take that information to guide our clients as their policies renew, and as new clients choose to trust us with their coverages.
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We have specialists in each sector of insurance, you'll meet them below - Tina, who oversees our personal lines Home and Auto. Jessica, who oversees our Commercial book of business. Micaiah who oversees the Medicare and Health insurance book of business, and specializes in placing high value home and auto coverage. Of course our owner Shawn who oversees the agency and handles some of our most complex commercial and personal accounts with clients who have been with her for more than a decade, moving from her captive agent appointment to Oakley Insurance Group.
Shawn Hellebuyck
Owner
Greetings, allow me to introduce myself, my name is Shawn Hellebuyck a licensed career insurance agent and insurance geek. It’s true, I’m fascinated with all things insurance.
Prior to starting Oakley Insurance Group in 2015, I was a Farmers Insurance Agent for nine years before that where I received multiple awards for my achievements including: Topper Club; Farmers Championship; and in 2015 the Zurich Achievement which is reserved for the Top 100 Farmers Agents in the nation.
Oakley Insurance Group shares the value that we love coverage – we work to emulate insurance inspired. Inspired by you, inspired by your family, inspired to keep you and your family protect from the unforeseen life can bring. We believe choice in insurance is empowering and that is why we started Oakley Insurance Group, to allow our clients choice and input in their insurance coverage.
I grew up in the city of Chicago, Illinois on Oakley Avenue (that name sounds familiar) and I was a lifeguard at Oak Street Beach in Chicago for seven years. If I wasn’t an insurance agent, I would still be an Oak Street Beach Lifeguard as that remains my second favorite occupation. I am proud to be a DePaul Blue Demon where I received a B.A. in Communications, and a scholarship Track and Field and Cross Country athlete. I was inducted into the DePaul Athletic Hall of fame for Cross Country. After one of my knees gave out and under doctor recommendation I've had to move my exercise to a stationary bike, but I am still very much passionate about exercise.
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Besides being a passionate insurance agent, and “Wine with The Sunset Aficionado”, I also volunteer for several pet rescues through Arizona. If you are in Tucson and you are interested in fostering pets, have homeless pets in your area, or need advice or assistance with pets in need, please reach out to us as we are a team of pet rescuers.
Tina Munton
Personal Lines Manager
Tina has made insurance her career for over twenty-five years, continuously striving to provide the best in coverage and service for her clients. Tina worked with Shawn at Farmers insurance before Oakley Insurance Group existed. Now, Tina oversees Oakley’s personal lines ensuring our customers and their property are adequately covered. Tina goes to great lengths as an agent reviewing policy renewals, policy coverages, fluctuations in premiums industry wide, and taking time to make sure every customer completely understands coverage, what they need, and why.
Tina’s mission as an agent is to retain customers through unmatched customer service not only using her knowledge as an agent but also as a mother and wife who knows the importance of making sure her family is covered.
Tina’s vision as an agent is to continue to grow within the industry as the industry itself grows. She sees herself remaining an integral part of the Oakley team, and to hone her skills as an agent to continue covering families and individuals for the things in life that bring us joy, and fun.
When Tina’s not geeking out in insurance, she’s with her family. Her husband and her daughters are the soft gooey center of life and adores spending time with them. When they can, they take their trailer up the mountain and get away for a bit, creating memories, and enjoying the company of fresh air and the bond of family time.
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Fun fact, depending on who you ask: Tina doesn't like coffee! *gasp*
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"When I'm making sure your family is covered, I ask myself, if this were my home, or my car, would I feel comfortable with the coverage and limits I'm setting?" - Tina
Micaiah Bennett
Medicare and Health Insurance Specialist
Agency Marketing and Development
Micaiah is a southern boy at heart, being from North Carolina and is sometimes referred to as a jack of all trades. His greatest passion in life is music and is a musician and composer. He took four years of culinary arts training. He has an intense passion for aviation. He enjoys the study of gems and minerals (some displayed on his desk). Even at one point, he had considered being an animator for Disney. He really enjoys photography, some of which you'll see hanging on the Oakley walls. Micaiah is also an entrepreneur at heart, owner of a few business, and utilizing some of those skills for the betterment of Oakley Insurance Group.
His first introduction to insurance was working for a primarily Medicare agency in North Carolina in 2014. In 2019 (before we knew the pandemic was coming) he resigned his current position as a Network Engineer to pursue his dream of being a Commercial Airline Pilot, obtaining his Private Pilot license in September of 2019. When the pandemic of 2019/2020 hit and his flight training forced to end, he decided to take some of that time to begin studying for his Health and Life license. After joining Oakley Insurance Group he began training for his Property and Casualty license and obtaining it shortly thereafter.
Micaiah brings diversity to the Oakley family in the form of different layers of knowledge and experience. Bringing his tech knowledge, and experience from the marketing company he owns, he has been able to improve upon the existing foundation created at Oakley Insurance Group.
Micaiah’s vision as an agent is to provide customer service beyond expectations, and to set himself apart from other agencies and other agents. He will use various skills and knowledge to grow as an agent and to bring that growth to the agency.
Micaiah’s mission as an agent is to supply every customer he works with the knowledge and understanding they need to make coverage decisions based on that knowledge. Knowledge is empowering, and to him it is important that the choices his clients make are with the correct knowledge and information to do so.
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Fun Fact: Other than the computer his dad bought him in 2006, every computer Micaiah has owned has been self-built.
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"Every agent is different, every customer is different, so it is important that our agency is diversified." - Micaiah
Jessica Richards-Finley
Commercial Lines Manager
Jessica is newest member of the Oakley Insurance Group family, having joined us in April of 2024 as a fully licensed and experienced insurance professional.
Jessica began her insurance career right out of high school, starting as a receptionist. During her time as a receptionist she studied for her insurance exams, first obtaining her Health and Life license. After a few years in the health and life space of insurance, she obtained her Property and Casualty license.
First and foremost, Jessica is a mother, grandmother, and wife. She is part of a large family from Benson, Arizona, and lived in Sierra Vista until 2021. When Jessica isn’t insurance-ing, she enjoys making silver jewelry, crocheting, and knitting. She also has a sporty side and enjoys playing softball.
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"I am very happy to be part of the Oakley insurance team. I believe in helping my customers become more educated, providing them a better understanding of their coverages, and allowing them to make educated decisions to better protect themselves." - Jessica
Jon Ellis
Agency Customer Support
Jon joined Oakley Insurance Group at the end of 2023 after being an Oakley client for many years, with a sparked interest in Life Insurance, and helping our agency.
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When Jon isn’t on the Oakley clock, he is an EMT which has been his career for over sixteen years. He has a beautiful wife, and two stepdaughters. He enjoys the outdoors, and participating in activities like camping and trail riding. Other hobbies and interests include renewable energy, HAM radio operation, IT networking and security, and a huge Bitcoin fan!
