Connected Conversations in Insurance | Heath Shearon

Published on

August 20, 2025

Contributors

Nick Berry

Demand Generation Marketing Manager

Nick is the Demand Generation Marketing Manager at Canopy Connect, where he brings 20 years of sales and marketing experience, including the last 6 years focused on broker tech companies. When he's not managing marketing campaigns, he's likely sipping on a dirty chai latte (hot) or building side projects to keep his skills sharp. Nick is a proud USAF veteran and a family man with 4 kids.

A few months back on Connected Conversations in Insurance, I had the chance to sit down with someone a lot of you probably know (or at least know of): Heath Shearon—better known as the Mayor of Insurance Town. And let me tell you, it was one of those conversations that just stuck with me. Heath has this unique way of balancing humor and insight, and in our chat, we covered everything from technology resistance in agencies to marketing strategies, legacy tactics making a comeback, and why industry events still matter.

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The Technology Hurdle We Still See

One of the big themes that came up was tech adoption, or more accurately, the lack of it in some corners of the industry. Heath didn’t sugarcoat it: “A lot of agents are still terrified of using technology in their agencies,” he said. And he’s right. I’ve seen it firsthand too. There are still agencies out there running on file cabinets or managing their books of business with Excel. Excel! In 2025! It’s not about shaming those agencies—it’s about recognizing the gap and figuring out how to help them bridge it.

Marketing: Finding the Sweet Spot

Heath and I also shared some back-and-forth on marketing ideas. We’ve both spent a lot of time on the insurance tech side, so we see the challenges agencies face in telling their story and getting in front of people. What I loved was Heath pointing out how websites are making a comeback. For a while, everyone was all-in on social media pages, but now agencies are rediscovering the value of having a real digital home base that ties everything together. As Heath put it, “It’s cool to see that come back.” I couldn’t agree more.

Old School Marketing with a New Shine

One of the more surprising parts of our talk? Direct mail. Yep, old-fashioned postcards and letters are finding their way back into marketing plans. Heath mentioned that with inboxes so overloaded, people are actually paying more attention to what shows up in their mailbox. I’ve seen agencies use this really effectively, pairing direct mail with QR codes or links that drive people straight online. It’s funny—what was once “old school” is now the thing that stands out.

Why Events Still Matter

If you’ve ever met Heath, you know he’s in his element at industry events. He’s not just attending—he’s engaging, speaking, and connecting. And during our conversation, he emphasized that events are still worth the time and energy. His point was simple: if you show up with the right intent and a game plan, you’ll walk away with way more than just a stack of business cards. I’ve seen it, too. Some of the best tech integrations and partnerships in our space started with a handshake at a conference.

Connect with Heath

Before we wrapped up the episode, I asked Heath the best way for people to reach him. No surprise there—he said LinkedIn. So if you’re looking to connect with him (and you should), that’s the place. If you missed this episode, I’d highly recommend going back to give it a listen. It’s a great one for anyone curious about where insurance tech and marketing are headed, and how some “old” ideas are finding fresh legs today.