WC Dillon Company was founded in 2001 in Nashville, Tennessee as an employee benefits insurance agency with the singular goal of building lasting client relationships. The insurance agency has grown and prospered, while building a reputation for providing outstanding service and expertise, and continues to achieve its founding goal every day.
In 2011, we formed a joint venture with Menard, Gates, and Mathis to broker property and casualty insurance. Following a merger with McDonnell Insurance Agency, we now operate our commercial and personal lines insurance business under the Insight Risk Management Brand. As an independent insurance agency, we represent the best insurance companies in the marketplace and protect our clients’ bottom lines with appropriate coverage at a competitive price.
The satisfaction achieved by providing great service, with integrity and skill, makes WC Dillon Company / Insight Risk Management a great place to work. We hire exceptional people who do exceptional work.
A native of Atlanta, Georgia, Chan has lived in Nashville since graduating from Vanderbilt University in 1993. In 2001, he co-founded DillonBrooks, an employee benefit insurance agency and built it into a thriving company before launching the full-service agency, WC Dillon Company in 2007. Chan understands how to help his clients run a successful business and is a valuable partner– consulting with them on both risk management and employee benefit programs.
Chan has volunteered with Big Brothers Big Sisters of Nashville since 1995, is a past board member of Safehaven Family Shelter, and current board member of Arts & Business Council of Middle TN.
A native of Lexington, Kentucky, and a 2006 graduate of Rhodes College, Matt began his business career as a property and casualty insurance producer in Memphis, Tennessee before joining WC Dillon Company / Insight Risk Management in August 2011. He combines strong technical insurance knowledge with the business acumen to fully interpret and mitigate a client’s exposure.
Matt is a member of the Phoenix Club of Nashville, providing fundraising support for the Boys & Girls Club of Middle Tennessee. He is also a current board member of the Insurors of Nashville and past board member of the Nashville Humane Association. He enjoys running, golfing and rooting for the Kentucky Wildcats.
A Nashville native, Raleigh is a Certified Insurance Counselor (CIC) with 15 years of experience in the commercial insurance and banking industries. He and his wife, Amy, have two daughters, a beagle named Fred, and a corgi named Wilma. Raleigh has volunteered with many non-profit organizations in Middle Tennessee, including St. George’s Kindergarten, Oasis Center, and Family Faith Medical Center. When he’s not in the office, you will find Raleigh in the great outdoors. In fact, he has hiked the entire Appalachian Trail. He loves mountain biking in Percy Warner Park, fly fishing on the Caney Fork River, and picking the mandolin with his bluegrass bandmates, The Green Hillsbillies.
Originally from Memphis, Tennessee, Cassidy specializes in Employee Benefits, HRIS, and ERISA compliance. She studied Marketing at the University of Memphis before earning her Economics degree in 2015. She then began her career in insurance as an Employee Benefits Account Assistant. In 2018, she moved to Nashville to join WC Dillon Company as the agency’s first HRIS Administrator. Cassidy is a member of the Society for Human Resource Management (SHRM) and Insurors of Nashville (ION), and she enjoys volunteering with Nashville Predators Foundation and Nashville Humane Association. Cassidy is tri-lingual in English, Spanish, and sarcasm. She is also the founder of BrandMe Graphic Design. When she’s off the clock, you can find Cassidy on a hiking trail, painting, playing with her niece and nephew, or taking a road trip.
Sherri has more than 15 years of experience in the insurance industry, specializing in medical, dental, vision, life, disability and voluntary worksite benefits. Originally from Columbus, Ohio, Sherri also lived in Kentucky, Florida, Louisiana, Illinois, Alabama and Nebraska before putting down roots in Nashville, Tennessee in 2009. Her hobbies include hiking, canoeing, training her pup, Millie, and complaining about the traffic on I-24.
Born and raised in Nashville, Tennessee, Cherié has worked in the insurance industry for more than 19 years, specializing in Property & Casualty on both the carrier and agency sides. She is a Certified Insurance Service Representative (CISR), is a current board member of Insurors of Nashville (ION), and was formerly board President in 2019. Cherié loves spending time by the pool with her husband, two children, four grandchildren, and fur baby. In her free time, she enjoys traveling with her husband, attending her granddaughters’ cheerleading competitions, and rooting for her grandson at his soccer and basketball games. She is also the owner of Monarch Blossoms, a custom silk floral design business.
Waddy was born and raised in Hilton Head Island, South Carolina, where he grew up going to the beach and spending his summers as a surf instructor. Waddy attended the University of Tennessee, where he earned a Bachelor’s degree in Retail Hospitality and Tourism Management with a minor in Business Administration before moving to Nashville, Tennessee in 2021 with his dachshund, Weezy. When he’s off the clock, you can find Waddy cheering on the Tennessee Vols, or playing soccer, golf, or tennis.
Tori moved from her hometown of Madisonville, Kentucky to Nashville, Tennessee in 2016 upon graduating from the University of Kentucky in 2015. She then began her career with the YMCA of Middle Tennessee before joining WC Dillon Company & Insight Risk Management in 2019. Her acute attention to detail and problem-solving skills make Tori an invaluable member of our team. She is also a Registered Dietetic Technician and a member of the Tennessee Academy of Nutrition and Dietetics. In her free time, Tori enjoys hiking, running, and volunteering with the YMCA.
Originally from Finland, Sherry has 20 years of experience in the insurance industry. She graduated with a degree in Business Administration from Wilson College and is a designated Associate in Personal Insurance (API). Sherry has been married to her husband, Pete, for 20 years, and together they have two fur babies, Sakke and Marley, both golden retrievers. Being a nature lover and having attended 60 Grateful Dead shows, Sherry truly has a hippie soul. She loves traveling, gardening, cooking, hiking, hugging trees, and rescuing dogs.
With over 35 years of experience in the insurance industry, Tammy is proficient in employee benefit administration and claims resolution. She is a native of Nashville, where she attended Trevecca Nazarene University before earning her PhD in Motherhood. In her spare time, Tammy enjoys tending to the family farm, where she resides with her husband of 40 years and four terrific children.
A native of Murfreesboro, Tennessee, Julia has worked with reputable insurance carriers and agencies since 1979, specializing in property and casualty insurance and excelling in client services. Julia enjoys traveling, spending time with her loving husband of over 40 years, and soaking up the Florida sun with her four grandchildren.
Born and raised in Smyrna, Tennessee, Tabatha Simpson began her insurance career in 2018. After 10 years in retail management, she decided to follow in her mother’s footsteps and is working towards becoming a Commercial Lines Account Manager. Tabatha brings her strong client service skills, attentiveness and enthusiasm to the agency. When she’s off the clock, you can find Tabatha creating DIY projects, traveling, and spending time with her two fur babies, Oliver and Jackson, both rescues.
John joined the agency with the opening of its Lexington, Kentucky office in 2021 after a decade in the aerospace industry, where he led a product develop team and managed client relationships. A Lexington native and University of Kentucky graduate, John’s technical background and energetic approach to sales serve him well as he embarks on a career in insurance. John is also a student pilot and novice golfer. His better half, Dr. Kristen Witt, is an elementary school teacher in Fayette County. Together, they enjoy traveling, social outings, and playing host to friends and family whenever possible.