Today we are speaking with Simon Glairy, a recognized expert in insurtech and the digital transformation of the insurance industry, with a specialized focus on risk management and AI-driven risk assessment. For years, the insurance industry has focused on streamlining transactions, often at the expense of meaningful client advice. Now, as technology reshapes the landscape, we sit down with Simon to explore the industry’s next major evolution. This conversation delves into how brokers can leverage new tools to deliver personalized guidance at scale, the critical strategic choices between building and buying technology, and why leadership, not software, is the ultimate determinant of a successful transformation. We’ll uncover how to balance a seamless, e-commerce-style experience with the irreplaceable value of human expertise, ensuring that brokers become true advisors rather than just digital facilitators.
Historically, the economics of insurance made it difficult to advise personal lines clients. How can technology now enable brokers to deliver meaningful guidance at scale, and what key metrics should they use to measure the impact of this new advisory model on client retention?
It’s a foundational problem the industry has skirted for decades. For personal lines and small transactional clients, the economics simply weren’t there for a broker to invest significant time in deep, advisory conversations. The model relied on call centers and outbound campaigns that, frankly, most customers just learned to ignore. It created a service experience that felt completely disconnected from how they managed the rest of their financial lives. Technology completely changes this dynamic. It allows us to interact with customers in ways that are both cost-efficient and non-invasive. Instead of just a renewal notice, we can now provide tailored guidance and insights that were previously reserved for large commercial accounts. To measure success, we need to look beyond simple retention rates. The key metrics are now about engagement and improved client outcomes. Are they interacting with the advice? Are they making better coverage decisions? That’s the real measure of a successful advisory model—deepening the relationship from a transactional touchpoint to a trusted partnership.
Consumers increasingly expect a seamless, e-commerce-like journey. As brokers adopt this model, how can they avoid becoming mere “digital order takers” and instead use these tools to enhance their advisory value? Please provide a step-by-step example of a successful integration.
That’s the central tension every modern brokerage faces. The baseline expectation has absolutely shifted; clients, whether individuals or small business owners, demand a journey that feels more like Amazon—fast, transparent, and full of choice. Clunky, paper-based processes are no longer tolerated. The trap, however, is investing in all this technology only to become a digital order taker, which completely erodes the value proposition that separates a broker from a direct channel or an aggregator.
A successful integration embeds advice into that seamless journey. First, you invest in the tools that create that effortless, modern experience, allowing clients to explore options easily. But—and this is the critical step—you don’t just stop at fulfillment. As the client moves through the digital process, the system should use their data to trigger proactive, advisory moments. For example, the platform sees a client selected a policy with certain limits. Instead of just proceeding to checkout, it could flag an automated-yet-personalized message from their broker: “I see you’ve chosen this option. Given the data you provided about your property’s location, I’d strongly recommend we discuss adding flood coverage. Here’s a link to my calendar.” This transforms the journey from a simple purchase into a consultative experience, reinforcing the broker’s value without adding friction.
When deciding to build, buy, or form an alliance for a new technology, how should a brokerage define its unique “secret sauce” versus a capability that just needs to be competitive? Could you walk through the practical decision-making process for choosing a partner for a critical function?
This requires a very disciplined, business-architecture approach. The old habit of trying to build everything from scratch is a surefire way to end up with slow, indistinguishable products. Leadership teams must be precise about where they differentiate and where they just need to keep pace. We frame this as a “build-buy-ally” strategy. The first step is to define your “secret sauce”—the capabilities where you intend to be truly distinctive and create a unique client experience. For those areas, we believe you should own the development and invest your internal engineering effort.
For everything else—the functions that are merely table stakes or need to be competitive—you look to partners. The decision process is straightforward. First, identify the capability. Second, ask the hard question: “Is this part of our core, differentiating ‘secret sauce’?” If the answer is no, then the smart move is to find a partner that brings scale, speed, and proven expertise. I often say, we’re a brokerage, not Google. It’s far more effective to combine our deep insurance expertise with a tech partner’s engineering and data prowess. That fusion is what creates something truly unique and disruptive, allowing you to move at a pace the market demands, rather than waiting for your internal teams to catch up.
Effective transformation often depends more on leadership than on tooling. What specific, actionable steps can a leadership team take to create a culture where diverse teams—like sales and engineering—collaborate to develop innovative products that actually drive revenue and improve client outcomes?
This is the most uncomfortable, and most important, truth in our industry’s transformation. You can buy the most sophisticated platform in the world, but without the right leadership and culture, it will fail. The problem is that many organizations are still run on legacy command structures, where decisions get dragged through multiple committees. The first actionable step is for leaders to set the right environment, processes, and controls, often by adopting frameworks like OKRs (Objectives and Key Results) that are common in digitally native firms. This creates clarity and speed.
Second, leaders must become bridges. They need to connect different generations and, critically, different disciplines. You can’t just hire a Gen Z tech wizard and expect them to understand the nuances of underwriting or the realities of a sales pipeline. The real work is creating an environment where engineers, salespeople, underwriters, and marketers can challenge each other respectfully, all anchored to the same goals: driving revenue and improving client outcomes. The most vital question a senior team can ask isn’t “Which vendor should we choose?” but “What type of leadership do we need to make this transformation stick?” Otherwise, you end up with teams that build some really cool things, but nothing that actually sells or moves the needle for the business.
What is your forecast for the role of the insurance broker over the next five years as AI and automation become more sophisticated?
Over the next five years, the role of the insurance broker will fundamentally pivot from a facilitator of transactions to a sophisticated risk advisor. AI and automation will master the mechanics of quoting, binding, and processing coverage, making those tasks seamless and efficient. This won’t make brokers obsolete; it will free them to focus on the much harder, and far more valuable, work of delivering informed judgment and strategic guidance. The competitive battleground is already shifting away from who can provide access fastest to who can deliver the most insightful advice. The brokers who thrive will be those who embrace technology not as a replacement for their expertise, but as a powerful amplifier that allows them to scale their advisory capabilities to a much broader client base than was ever economically viable before. The future broker’s value will be measured in the quality of their counsel, not the speed of their clicks.
