Company History

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.

Our Team

Chan Dillon


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.

Matt Felgendreher, CIC

Executive Vice President

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. In his current role as Executive Vice President, he oversees the commercial lines department of the agency, mentors new producers, and manages client relationships. Matt is a Certified Insurance Counselor (CIC).

Matt is a board member of the Insurors of Tennessee/Big I and recipient of the Insurors Young Agent of the Year award. He is also a legacy member of the Phoenix Club of Nashville, past-president of the Insurors of Nashville and past board member of the Nashville Humane Association. Matt and his wife Tori enjoy running, golfing and rooting for the Kentucky Wildcats.

Raleigh Harwell, SVP


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.

Sherri Bashore

Employee Benefits Specialist

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.

Waddy Brooks

Personal Lines Account Assistant

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.

Sarah Fisher

Personal Lines Account Manager

Sarah, a native of Crossville, TN, has over a decade of experience in the insurance industry, specializing in personal lines. She has joined our team as a Personal Lines Account Manager. Her interpersonal skills and ability to connect with people make her approachable and easy to work with. Outside of work, she enjoys spending time with her two children and her furry family members.

Sherry Piper, API

Personal Lines Division Manager

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.

Tammy Russell

Employee Benefits Account Manager

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.

Julia Simpson

Senior Commercial Lines Account Manager

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.

Lindsey Gordon

Commercial Lines Account Manager

Lindsey has been in the insurance industry for over 5 years. She was born and raised in Racine, Wisconsin where she grew up a Packers, Brewers, & Bucks fan. She moved to Nashville, Tennessee with her fiancé and golden retriever Obi to be closer to family & longer summers. Lindsey played competitive soccer through high school and continues to stay active by working out, hiking & going for bike rides. She has auditioned for Survivor multiple times hoping to live out her dream of becoming the next sole survivor.

Tabatha Simpson

Commercial Lines Account Assistant

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 Witt

Account Executive

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.

Jennifer Taylor

Commercial Lines Account Manager

Jen was born and raised in Panama City, Florida and remains a big Gator fan even after moving to East TN in 2000. Jen has been working in the insurance industry for 15 years, finding her niche and passion as a Commercial Lines Account Manager.

She and her husband Stacey have been married for 23 years and are the proud parents of two children and two granddaughters who call her Mimi, and a Mini Schnauzer and Aussie Doodle. She loves to hike, camp, explore the outdoors, and new adventures. When not traveling she enjoys relaxing with her husband and family, and especially the time with her granddaughters.

Sam High

Account Executive

Sam joined the agency in December of 2022 after 4.5 years in the financial technology industry. A native of Birmingham, Alabama and a graduate of the University of Mississippi, Sam’s engagement in the local community, service oriented approach, and technical acumen serves him well in his sales position. He is a licensed insurance professional in P&C and holds his CLCS (commercial lines coverage specialist) designation. Sam is a member of The Phoenix Club of Nashville, a non-profit organization serving underserved youth in the Greater Middle Tennessee area. He is also 3-year Head Coach for the 6th grade basketball team at Christ The King Catholic School. Sam enjoys running, playing basketball, fishing, being with his black lab (Gus) and cheering on the Ole Miss Rebels