Today we’d like to introduce you to Will Canterbury.
Hi Will, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
I grew up on a farm in a very rural part of Mississippi—so rural, in fact, there wasn’t a single red light in the entire county. My dad and I worked side by side raising cattle and farming row crops. When shifts in the agricultural industry forced us to adapt, we took a leap and started my first business when I was just 17 years old. What began as a small lawn service quickly grew into a major operation in the Jackson, Mississippi area, with clients like Pepsi, Ford Motor Company, and every Walgreens location in the metro area. My dad still runs that business today.
After graduating high school, I attended Ole Miss, earning my degree in 2006. From there, I moved to Washington, D.C., where I worked for a Member of Congress and design a press package distributed to every congressional member within her party. That experience led me to Tennessee, where I joined the Office of the Lieutenant Governor. During my time there, I served as Constituent Services Director, acted as the office’s Second Amendment subject matter expert, and served as a liaison to Senate legislative staff and other state agencies. I was also involved in political campaigns, co-directing state senate races and directing the western region of a gubernatorial campaign.
Music had always been a driving force in my life and what initially drew me to Nashville. Like many, I arrived with big dreams of making it in the industry. While that path didn’t unfold the way I envisioned, it ultimately led me to discover my passion and strengths in sales.
I began my sales career as a wholesale furniture representative for Lane Furniture Industries, covering the southern half of Mississippi and the entire state of Louisiana. At the same time, I was commuting back to Nashville on weekends to see my girlfriend—now my wife, Tali. Between work travel and personal trips, I put over 65,000 miles on my car in just five months. It was an intense season that eventually brought me back to Nashville full-time.
Once back, I joined RJ Young as a territory sales representative. In 2014, I was the only territory rep in the company to secure a Top 5 deal, closing an account valued at nearly $500,000.
After RJ Young, I transitioned into the insurance industry—something my uncle, Robert “Bob” Pierce, had encouraged me to pursue years earlier. At the time, I couldn’t have imagined a more boring career path, but he was right. Bob was an industry titan and highly respected leader at Allstate, earning the company’s top honors multiple times, and his guidance proved invaluable.
I began as an agent with Nationwide Insurance in 2015, and in 2017, I had the opportunity to co-own my first agency, Nville Insurance Group. After navigating some challenging business circumstances with my former partner that led to its closure in 2022, I launched The South Insurance Agency—a true phoenix rising from that experience.
Today, The South Insurance Agency is larger than my previous venture and continues to grow rapidly. We are currently expanding our team and are in the process of adding two more agents, bringing us to a team of seven. Our agency is built to be a true one-stop shop, offering coverage for homeowners, auto, motorcycle, boat, RV, ATV, renters, high-value homes, classic cars, and more. As an independent agency, we partner with top carriers such as Auto-Owners, Travelers, Safeco, GEICO, National General, Progressive, and Openly to provide clients with the best coverage options at competitive rates.
We also specialize in commercial insurance, which is a major focus of our business. As a Commercial Lines Coverage Specialist (CLCS), I work closely with business owners to provide tailored solutions including general liability, commercial auto, workers’ compensation, umbrella policies, equipment coverage, and more.
In addition, we offer life insurance and professional liability coverage. Simply put, there’s not much we can’t insure—we’ve even covered stunt shows featuring cars flying through the air.
The vision for The South Insurance Agency is to become synonymous with insurance across the Southern United States. Our goal is to become synonymous with insurance in the SEC region, with local agents in every state within our logo border. We’re already making significant progress, with four agents in Tennessee and one in North Carolina, and plans to expand further with additional team members in both Tennessee and Mississippi.
Outside of work, I’m blessed with an incredible family. I’m married to my wife, Tali Canterbury, who is an accomplished entrepreneur in the Nashville music industry and co-owner of 50 Egg Music. She also earned her law degree while simultaneously balancing multiple jobs—she is a phenom. Together, we have three wonderful children—Lennon, Lyla Joy, and Liam—as well as our fur baby Australian Shepherd, Georgia.
Music continues to be an important part of my life. I serve on the praise team at Grove Hill Church in Chapel Hill, Tennessee, where I play electric guitar, acoustic guitar, drums, and contribute vocals.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Not at all. I have definitely had my share of challenges from supervisors who were threatened by a rising team member, to promises broken by former bosses, going from the top sales position to getting blind sides 3 months later, a business partner that used company funds on a young woman on TikTok, etc. I have rebranded or reinvented myself almost 10 times in my life and keep rising. You can’t beat a man that refuses to quit.
We’ve been impressed with “The South” Insurance Agency, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
The South is built to be a true one-stop shop, offering coverage for homeowners, auto, motorcycle, boat, RV, ATV, renters, high-value homes, classic cars, and more. As an independent agency, we partner with top carriers such as Auto-Owners, Travelers, Safeco, GEICO, National General, Progressive, and Openly to provide clients with the best coverage options at competitive rates.
We also specialize in commercial insurance, which is a major focus of our business. As a Commercial Lines Coverage Specialist (CLCS), I work closely with business owners to provide tailored solutions including general liability, commercial auto, workers’ compensation, umbrella policies, equipment coverage, and more.
In addition, we offer life insurance and professional liability coverage. Simply put, there’s not much we can’t insure—we’ve even covered stunt shows featuring cars flying through the air.
The vision for The South Insurance Agency is to become synonymous with insurance across the Southern United States. Our goal is to establish a strong presence throughout the SEC region, with local agents in every state within our footprint. We’re already making significant progress, with four agents in Tennessee and one in North Carolina, and plans to expand further with additional team members in both Tennessee and Mississippi.
What’s next?
I plan to have at least one agent domiciled in every state within our logo border. We have implemented AI into our work flows, not to replace employees but to enhance what they can do and make it more efficient. The South is moving to a place where it sets the bar for others to follow.
Pricing:
- All insurance is customized, despite certain commercials that you see. We will find what you need at the best price possible.
Contact Info:
- Website: https://www.thesouthinsurance.com
- Instagram: https://www.instagram.com/thesouthinsurance/
- Facebook: https://www.facebook.com/thesouthinsuranceagency/
- Twitter: https://x.com/TheSouthInsures
