Building Community and Embracing Digital Transformation in Insurance
With our second season of Connected Conversations in Insurance coming up, I wanted to highlight one of my favorite episodes with Kevin Spann, a seasoned insurance professional and owner of five Allstate Insurance Agencies in Queens, New York. Our conversation covered many topics, from the importance of being adaptable in business to fostering community connections.
The Evolution of an Insurance Career
Kevin's journey into the world of insurance started out of necessity. As he shared, "I needed a job, a real job... I was able to break into Allstate after the third interview." From there, his career flourished, transitioning from an entry-level life underwriter to owning multiple agencies. Kevin recalled his initial realization of the potential in owning an agency: "whet my appetite... knowing that work could lead to income and a better life."
Adapting to Digital Demands
Adaptability and efficiency emerged as key themes in our conversation. Kevin emphasized how the pandemic accelerated the need for digital operations within the industry. "Everyone learned to work from home…we're all ordering more on Amazon," he noted. He championed technology's influence on operations, particularly through tools like Canopy Connect, which streamline the insurance process and enhance customer service.
Championing Community Involvement
Community involvement has always been at the heart of Kevin’s success. As he put it:
"There’s an old saying, not mine, that says you can get anything you want if you help enough other people get what they want. So I’ve always led with community."
When Kevin opened his agency in Middle Village in 2007, he didn’t know anyone in town. His first move wasn’t a flashy marketing campaign. It was sponsoring a local Little League team. That $400 sponsorship became the seed of countless connections. From there, Kevin said “yes” to nearly every community opportunity that came his way—from Relay for Life, to new youth sports leagues, to local property owner associations. Each grassroots effort opened unexpected doors, including partnerships, speaking opportunities, and even a steady stream of interns who’ve helped Kevin’s agency embrace digital transformation.
For Kevin, community isn’t just good business—it’s everything. Those relationships built trust, visibility, and staying power that advertising alone could never buy.
And when the pandemic disrupted his in-person networking routine, Kevin leaned on that same spirit of connection to launch his podcast, first spotlighting local business leaders, and today interviewing agents nationwide in his ambitious 50 agents, 50 states series.
Kevin’s story is a reminder that when you invest in people, doors keep opening.Insights into Running Multiple Agencies
Operating five agencies under one roof is no small feat, and Kevin attributes his success to a strong leadership team. "We hire good people and have a good leadership team," he explained. This combination of leadership and strategic thinking allows him to ensure both quality and growth.
The Value of Local Expertise
Kevin's podcast, "Wind Down with Kev," delves into regional insurance insights across the U.S. He shared anecdotes from agents dealing with diverse risks, from 80 mph winds in New Hampshire to wild elks in Montana. "The value of the local agent is their unique knowledge," he remarked, underscoring the irreplaceable insight these agents bring to their communities.
Looking Forward with AI and Mentorship
Beyond his core insurance business, Kevin is passionate about mentoring and the potential of AI. He highlighted his work with chatbots and AI tools, emphasizing their transformative power: "The need for knowledge about how to integrate AI into your system is desperate." Kevin is on a mission to demystify AI for insurance professionals and harness its power to drive business innovation.
His story is a testament to the power of adaptability, community engagement, and embracing the digital transformation that the insurance industry is undergoing. I invite everyone to follow Kevin and listen to his conversations at "Wine Down with Kev," where he continues to share exceptional stories and insights.