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There were so many pearls of business wisdom shared during this year’s PropertyCasualty360 Agency of the Year Winners Roundtable on LinkedIn.
For the first time, my team and I selected two Agency of the Year award winners instead of three, as we have in the past. Although there were many fine entries, including a handsome stable of finalists, we felt the winning pair stood out for their relatable business narratives and best-in-class insurance operations.
Mounting professional recognition programs and events is one of the perks of working at PropertyCasualty360. As I said during the Winners Roundtable, my colleagues and I love opportunities to showcase the excellence, the heart, and the smarts behind the insurance industry.
This year’s Agency of the Year award winners reflect disparate but connected corners of the insurance ecosystem. One winner is firmly rooted in its community, and proves that no matter how modern insurance becomes, it is a business of timeless values. The other winner is rooted in digital life but recognizes the importance of personal connection to consumers as they navigate money and finance.
Both operations are tackling common insurance-business challenges such as fostering strong and lasting relationships and weathering fiscal turbulence.
You can take a closer look at the 2025 Agency of the Year award winners here and here.
…Or watch the LinkedIn roundtable recording.
After a too-early-in-the-morning introduction from me — someone please remind me to hook up the intravenous espresso drip before getting in front of a camera — Senior Editor Brittney Meredith Miller chatted with this year’s winners on such topics as balancing digitization with personalization, AI’s best insurance uses, and finding and retaining great staff.
Both winners talked about the importance of fostering and nurturing strong relationships — with partners, employees, and communities.
“In everything we do with technology, people come first,” said Mark Gannon, CEO of Gannon Associates Insurance. "We look at it as, 'Is this a solution that’s going to help us engage in a better way?'"
The measure of any technology tool employed by Gannon Associates is how well it helps the agency to better serve its customers. “You have to try and find that solution that’s going to work for you, and there will be trial and error doing that,” said Gannon, echoing a sentiment often heard among today’s Main Street insurance agencies.
Meanwhile, at The Zebra, Vice President Katie Gold and her colleagues are acutely aware of the humanity behind the insurance business. “It's about finding that balance between speed and efficiency and meeting the needs of the consumer when it comes to covering what matters to them most,” Gold said.
Both agencies view recruitment as an ongoing business imperative. In addition to charging everyone in the company with uncovering great potential recruits, Gannon Associates has invested in a full-time trainer for the agency. “Educating and helping people move forward; word gets around about that, and you become a sought-after place of employment,” Gannon said.
He added that workplace culture has to be about more than just work for today’s top recruits.
The Zebra returns to timeworn company values when it comes to luring recruits. Its remote-work culture also attracts professionals who want balance and flexibility. “We’ve found ways to stay connected while working remotely, and that’s been really big for us,” Gold said.
Workplace superfood for the seasonal shift
These days and weeks after Daylight Savings in the U.S. can be tough at work, as teams buckle down and strive to complete projects and meet yearend KPIs before the winter holidays. Anyone in need of a work-life adrenaline boost should seek out conversations and content like the 2025 Agency of the Year Winners’ Roundtable as a reminder that business superheroes are people just like us. The only difference is, they are expertly tuned in to the skills, systems and supporters that produce enviable results.
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