In the rapidly evolving world of insurance, few voices carry as much weight as Simon Glairy, a renowned expert in insurance operations and Insurtech. With a deep focus on risk management and AI-driven risk assessment, Simon has been at the forefront of guiding insurers through the complexities of digital transformation. Today, we dive into his insights on “The Great Rewiring,” a seismic shift in how the industry operates, who’s leading the charge, and what it means for the future of insurance. Our conversation explores the changing roles of operations leaders, the impact of customer expectations, the hurdles of legacy systems, and the path to successful modernization.
Can you walk us through what you mean by “The Great Rewiring” in the insurance industry?
Absolutely. “The Great Rewiring” is my way of describing a fundamental overhaul in the insurance sector. It’s not just about swapping out old tech for new; it’s a complete rethinking of how decisions are made, who makes them, and how systems and people interact. Unlike previous changes that were often tech-driven, this shift is about aligning technology with real business needs—think billing accuracy or customer satisfaction. It’s a rewiring of accountability and power, moving away from siloed departments to a more integrated approach where operations and technology are inseparable.
What’s driving this major shift at this particular moment?
Several forces are converging right now. Automation and AI are no longer just experiments; they’re core to how we handle underwriting, claims, and customer service. At the same time, customer expectations have skyrocketed—they want the same seamless digital experiences they get from retail or banking. Add to that the intense cost pressures and regulatory demands for measurable results, and you’ve got a perfect storm. Insurers can’t afford to drag their feet anymore; they have to adapt quickly or risk falling behind.
Why are operations leaders stepping into a more prominent role in digital transformation compared to traditional IT leaders?
It comes down to proximity to the problems. Operations leaders live in the day-to-day realities of the business—things like billing errors or delays in policy issuance. They feel the pain points and understand the impact on customers and costs in a way that’s often more immediate than IT leaders, who historically focused on infrastructure or platforms. Ops leaders aren’t just implementing tech; they’re defining what outcomes matter most, making them critical to driving meaningful change.
What unique perspectives or skills do operations leaders bring to this transformation process?
They bring an intimate knowledge of workflows and friction points. They know exactly where a billing system fails or why customers get frustrated with a process. This isn’t abstract to them—it’s their daily grind. They also tend to have a knack for translating business needs into actionable tech requirements, bridging the gap between what the company needs and what technology can deliver. That practical, ground-level insight is invaluable when you’re prioritizing investments or choosing vendors.
How are customer expectations influencing the push for digital transformation in insurance?
Customers today expect insurance to be as easy and intuitive as shopping online or using a banking app. They want instant quotes, digital payments, and real-time updates on claims—all with a few clicks. If an insurer can’t deliver that, nearly two-thirds of consumers say they’d consider switching to one that can. Falling short doesn’t just mean losing a customer; it risks damaging trust and reputation, which are the bedrock of this industry. So, meeting these digital demands isn’t optional—it’s survival.
With only a quarter of transformation initiatives in insurance being highly successful, what do you see as the main reasons so many struggle?
A big issue is misalignment between technology and business goals. Too often, projects are driven by the allure of new tools rather than solving specific operational challenges. Legacy systems also play a huge role—88% of executives say they’re a drag on progress because they’re slow, inflexible, and costly to replace. Then there’s the human factor: resistance to change, lack of skills, or unclear leadership. Without a clear vision and strong execution, these initiatives just fizzle out.
What role can operations leaders play in boosting the success of these transformation efforts?
Operations leaders are uniquely positioned to ground these projects in reality. They can ensure that every tech investment ties directly to a business outcome, like faster claims processing or fewer billing errors. They’re also the ones who can rally teams around change, since they understand the day-to-day impact. By acting as a bridge between IT and the broader business, they help keep everyone focused on results, not just deployment.
You’ve described operations leaders as “agents of transformation.” Can you paint a picture of what that looks like in action?
It’s a shift from being reactive to proactive. Instead of just keeping the trains running on time, they’re redesigning the tracks. Picture an ops leader spotting a bottleneck in policy issuance—they don’t just report it; they work with IT to spec out a digital solution, test it with real workflows, and measure the impact on speed and customer feedback. They’re not coding the software, but they’re shaping how it’s built and ensuring it solves the right problem. It’s about owning the change, not just managing it.
Given that legacy systems are such a barrier, how should insurers decide where to start modernizing?
Start with the pain points that hit customers and costs hardest. Operations leaders can pinpoint which systems—like outdated billing platforms—cause the most errors or delays. From there, prioritize based on impact: Will replacing this system improve customer retention? Cut operational costs? It’s also about feasibility—some systems are so entrenched that replacing them overnight isn’t realistic. A phased approach, where you modernize critical pieces while maintaining stability, often works best.
Looking ahead, what’s your forecast for the future of digital transformation in insurance?
I see it accelerating, no question. With the digital insurance platform market projected to hit $229 billion by 2029, the investment is there, and the urgency is only growing. Operations leaders will continue to take center stage, evolving into hybrid roles that blend business and tech expertise. I also expect AI and automation to become even more embedded, not just in back-office tasks but in personalizing customer experiences. The insurers who succeed will be those who can balance speed with strategy—adopting new tools without losing sight of the outcomes that matter most to their customers and bottom line.
