Declaration of Independents: Will Canterbury

• By: Will Jones
• January 1, 2026

Will Canterbury

Owner

The South Insurance Agency

Nolensville, Tennessee

Will Canterbury is an entrepreneur in the truest sense. When he was 17 years old, he started a lawn care business that took care of some notable clients. After attending college, he worked for two political offices while trying to make it in the music industry in Nashville.

When neither path proved to be the right one, he reinvented himself again, taking jobs in wholesale furniture and copier sales. Eventually, bringing together all his experiences, he took the advice that his uncle—an executive at Allstate—had given him back when he was 19: Try a career in insurance.

“At the time, wanting to be a rock star, it sounded boring—but now, years later, I love what I do,” he says. “I co-owned my first agency from 2017 to 2021 and went on to launch my own agency, The South, in March 2022.”

Goals?

My goal is to build a regional brand synonymous with insurance. I want a licensed agent in every state within our logo’s border, aiming for significant market share in the Southeast. When people ask about this ambitious goal, I quote Muhammad Ali: “If your goals don’t scare you, they’re not big enough.”

Keys to success?

I always give the glory to Christ Jesus. I don’t believe I’d be where I am today without God guiding the whole process. Yes, hard work plays a part, but the overwhelming majority of it comes from my faith.

Avoiding burnout?

Burnout is a real issue for agents, especially agency owners. One thing I’ve had to learn is not to sacrifice your family for the business. At the end of our lives, nobody will care how many insurance policies we’ve sold. But what our kids will remember is whether Dad was there to play and throw a ball around.

Advice for other salespeople?

The biggest key is figuring out who you are. Your approach will naturally be different from someone else’s simply because of how you communicate. Knowing yourself—your strengths and weaknesses—and presenting yourself authentically is critical. You don’t want to come across as a fraud or a greasy salesperson.

You have to focus on building relationships. This is especially true in insurance. Unlike some sales, you’re not convincing people that they need insurance—they already do because of legal or financial requirements. Half the battle is already won. Your job is simply to convince them to get it from you.

How to build strong relationships?

Build the relationship, spend time understanding the person, and focus on what they truly need. When you focus on building trust and rapport, the sale comes naturally. I’ve long believed the traditional sales triangle is upside down. Traditionally, the top is a brief conversation to build trust and rapport, and the close is the biggest part. I think it should be the opposite.

Spend more time on trust, rapport and needs analysis, and the close becomes automatic. If you’ve created a bond with a customer and they genuinely want to do business with you over someone else, the close is simple.

Marketing your agency?

We work with a company that handles our search engine optimization (SEO) and online presence across Google and other search engines. In the zip codes we target, we typically rank third to fifth in search results, even competing against State Farm and Farm Bureau. I’ll never have the advertising budget to outspend them, so being in the third-to-fifth range is more than fine.

We’ve also used Trusted Choice®, which is part of an insurer membership program, and we’ve leaned heavily on social media. Also, social media pages, like our local 411 pages, are extremely valuable and underutilized.

Making it easy for people to contact you?

I’m a big proponent of QR codes. People have gotten used to instant access—they don’t want to write down emails or websites. A QR code makes it easy: Scan it and go directly to a quoting page. We’ve put QR codes on business cards, advertising, even guitar picks for our agent who’s a musician. Anything that lowers the barrier for contact increases the chance of starting a conversation.

Using technology?

Our agency uses NowCerts as our agency management system (AMS) platform. Every time a new customer is added to the system, an automatic email goes out. I personally rewrite all of these emails because most of the defaults read like Hallmark cards—nobody talks like that. I write ours with Southern hospitality, and every email ends with “Welcome to the South”—our slogan.

We’ve also integrated artificial intelligence (AI) into NowCerts. For tasks like entering vehicle identification numbers (VINs) or driver information from PDFs, the AI pulls the data and inputs it into our system, saving 20–25 minutes per task. I haven’t used AI for phone interactions because I want to maintain the personal, Southern experience that differentiates our brand.

Time saved from AI?

Those 25 minutes make a big difference, but for my team and me, it looks different. As the agency owner and principal, I still get stuck doing tasks I don’t enjoy. I’m a salesperson at heart—I love cold calling, relationship-building and the sales side of the business. What I don’t enjoy are things like payroll and other back-office tasks. I prefer the people-facing side of the business.

So, with that extra 25 minutes, I might get ahead on payroll, send service updates to the team, work on quotes or make another client call myself. I still handle some of that work personally.

Finding the right hires?

All of my agents are commission-only, but I pay a higher percentage than most agencies. I’m looking for driven people who don’t need to be babysat. I tell them, “Go sell insurance on a pontoon boat in the middle of Percy Priest Lake if you want. I don’t care. You’re in charge of your paycheck.” If you want to take a week off, that’s fine, but your income depends on what you hunt and close.

I look for tenacious people who are willing to work hard and better themselves. I also rely on my wife, who is an attorney and entrepreneur in the music world. She acts as a human barometer. After I interview someone, she meets with them and can tell within minutes whether they’re trustworthy and cut out for the role. Her judgment is uncanny, and I’ve learned to trust it.

Ultimately, hiring the right people is partly about skill, partly about temperament, and partly about that X factor you can’t quite explain.

Trends impacting insurance?

I’m interested to see what AI does—it’s definitely a potential threat. I don’t know how many business owners in commercial lines would fully trust it without an agent guiding them. In home and auto, people already quote policies online, which is fine until a claim situation arises. That’s when the relationship with an agent really matters.

A bigger concern for me in any sales role is the decline in conversational skills. Younger generations often communicate via text, even when sitting at the same table. They struggle with face-to-face conversation. Studies suggest that skilled salespeople will be in high demand simply because many people can’t build relationships effectively. It will be interesting to see how the workforce evolves, given these communication shifts and the rise of AI.

Will Jones is IA editor-in-chief.