Three CEOs on Building the Future of Insurance Distribution

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The insurance brokerage business is in the midst of a once-in-a-generation transformation. Cloud computing is mainstream, artificial intelligence is moving from buzzword to business tool, and the competition for next-level talent has never been fiercer. 

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For three brokerage CEOs—Dan Keough of Holmes Murphy, Mike Tiagwad of Conner Strong & Buckelew, and Ric Stoakes of UNICO Group—the question is no longer if technology will redefine distribution, but how fast and who leads the way.

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BrokerTech Ventures (BTV) brought these leaders together at BrokerTech Connect in Chicago to discuss the forces reshaping the industry and the role BTV plays as the hub for forward-looking innovation.

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From Cloud to AI: Technology’s Inflection Point

Just a few years ago, the leap from on-premise servers to the cloud felt revolutionary. Today, these CEOs view that shift as the foundation for something even bigger.

• Mike Tiagwad described Conner Strong’s progress: “When our CIO came on board about five or six years ago, we really started migrating in earnest. We’re about 95 percent cloud-based now, which positions us for AI’s flexibility and scalability.”
• Dan Keough added that Holmes Murphy had to build the internal muscle first. “Seven or eight years ago we didn’t even have a CIO we trusted to lead our technology efforts. We organized our data, hired the right team, and now tech is front and center in every decision. The next generation expects technology to work for them, not the other way around.”
• Ric Stoakes noted UNICO’s own journey: “We moved some systems off-site, back on-premises, and now we’re almost 100 percent back to the cloud. By 2026 even our telecom systems will be fully cloud-based. The bigger challenge now is leveraging data and making sure tech truly serves our people, clients, and carrier partners.”

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Investing for Impact

If each firm suddenly had an extra $10 million to deploy, all three CEOs would balance bold bets with pragmatic returns.

• Keough said he’d “start a new Holmes Murphy from scratch—Holmes Murphy 2.0—designed with the end in mind,” with roughly half the investment earmarked for talent. “Technology costs have dropped, but we’re paying for the new and the old, so talent is the differentiator.”
• Stoakes outlined UNICO’s expansion beyond its Nebraska roots. “We’ve built national programs in aviation, construction equipment, trucking—much of it tech-driven. With added capital, we’d accelerate embedded AI in our agency management system and strengthen carrier API connections to quote and bind faster.”
• Tiagwad focused on acceleration: “I’d put the money toward high-quality people and outside expertise to move our initiatives faster—getting to the data-lake vision and system tweaks that create measurable ROI.”

Across all three, the theme is clear: technology matters, but the people who can wield it matter more.

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The Talent Shift

The talent conversation is no longer limited to producers and service staff. Data scientists, analytics pros, and AI specialists are becoming integral across departments.

• Stoakes described UNICO’s approach: “We’re embedding data-analytics skill sets right at the desk. These employees carry a small book of business but also serve as internal experts so innovation doesn’t break down between idea and execution.”
• Tiagwad expects “a greater and greater percentage” of hires to come from analytics and AI backgrounds as cloud systems reduce the need for old-school IT maintenance.
• Keough emphasized that technical chops alone aren’t enough. “We can hire brilliant people, but if they don’t understand the customer, they can’t make an impact. We need smart, tech-savvy hires who also ‘get’ our business and our clients.”

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BrokerTech Ventures: The Collaborative Catalyst

Each CEO credits BTV with accelerating their technology strategies and changing the culture inside their firms.

• “Five or six years ago, our technology area didn’t know enough about the business side, Tiagwad admitted. “Now, through BTV, we waste less time and have more wins. We’re collaborating with peers and carriers in a way that simply didn’t exist before.”
• Keough sees BTV as a strategic imperative for private brokerages. “Holmes Murphy has made more than 60 tech investments and run hundreds of pilots through BTV. If we want to stay independent forever, we need the best talent and the best risks—and that means leaning into innovation together.”
• Stoakes calls it a ten-out-of-ten experience: “It gives our people something aspirational. Insurance distribution is about entrepreneurship and solving problems. BTV shows recruits and carriers that this industry is innovative and exciting.”

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The Infinite Game

Despite different geographies and growth strategies, Keough, Tiagwad, and Stoakes share a long-term mindset. As Stoakes put it, “There’s no finish line for organizations. We’re playing the infinite game—building perpetual companies and a stronger industry. It’s a journey.”

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That philosophy is at the heart of BrokerTech Ventures. By convening the industry’s most forward-thinking brokers and the startups that challenge them, BTV has become a hub for collaboration, innovation, and the next generation of insurance distribution.

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For brokers wondering how to stay ahead, the takeaway from these CEOs is simple: Invest in talent, embrace technology, and collaborate continually. The future of insurance belongs to those who do all three.

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