On July, 1, 2025, Charles Taylor InsureTech hosted an exclusive roundtable with senior leaders from across the insurance sector to explore the state of digital modernisation. The session brought together a range of perspectives, from underwriting and operations to product and technology, with a shared focus on how the industry can move faster, smarter and more confidently into the future.
This conversation was also anchored in findings from Charles Taylor’s recent research, which surveyed over 100 large insurance organisations. And, while the data provided a vital backdrop, it was the lived experience of attendees that brought those insights to life.
There was immediate alignment around the central issue: legacy technology is holding the industry back.
Eighty-four percent of decision makers say their organisations are still reliant on legacy systems, and the impacts are felt across the board, from integration and scalability to customer experience and innovation. However, as one participant described, “It can be quite a big leap between legacy and modernisation, and it can be difficult to get this right.”
The group agreed that the challenge is not just technical, it’s also cultural. While resistance to change has largely disappeared from boardrooms, internal expectations and delivery models haven’t always kept pace. As one attendee put it, “It’s not about resistance anymore. It’s about execution.”
The research shows that 94% of those surveyed agree that their senior leadership supports digital modernisation. However, there’s a gap between support and mindset. Cost-consciousness, risk aversion and conventional thinking are still common descriptors for leadership teams.
That said, there was optimism in the room. Several attendees spoke about a shift in mindset already underway, particularly in organisations that have simplified governance, embraced cross-functional working and focused on getting the right foundations in place.
And, as one participant summed it, “The cultural shift has happened. The mindset is there. Now it’s about doing it, and doing it well.”
The research revealed that there are a number of challenges that insurers are facing when it comes to upgrading their legacy technology. Significantly, one in four (24%) of organisations struggle to identify suitable insurtech partners, underlining a necessity for assistance in navigating the insurtech market.
In the room, there was strong consensus that insurtech providers have a critical role to play in enabling modernisation – not by replacing everything, but by helping insurers move faster and more flexibly. Attendees also spoke positively about the ability to plug in components of the value chain rather than rebuilding entire systems. This modular approach allows for quicker implementation and better alignment with specific business needs.
However, there was also a note of caution. The group discussed how the volume of capital that has flowed into insurtech in recent years has created a crowded and fast-moving market. Some solutions become outdated before they’re even implemented. Others try to do too much.
The message here was clear: insurers want insurtech partners who understand the complexity of the industry, who can offer scalable and tailored solutions, and who are willing to co-create rather than just sell.
The final part of the discussion focused on AI, and the mood was pragmatic. Several organisations have already embedded AI agents into their operations, particularly in underwriting and claims. These tools are helping to analyse documents, surface insights and reduce time spent on tasks.
There was recognition that AI can drive real internal efficiency, from pricing models to productivity tools. But there was also a shared understanding that AI is not a silver bullet.
“AI is the new internet,” one attendee remarked. “It’s going to be everywhere. But we need to be thoughtful about how we use it, and where it adds value.”
Participants stressed the importance of understanding the use case, the regulatory environment and the potential for bias. In sectors like health insurance, for example, customers still want to talk to people. After all, AI can support but it can never replace.
At the end of this lively discussion, Charles Taylor InsureTech demo’ed their Virtual AI Call Agent which allows customers to make claims. The demo appeared to surprise the group, showcasing AI that was able to course-correct, convey empathy and recall complete claims details back to the customer.
The roundtable closed with a sense of momentum, as participants showed strong appetite for change at their organisations and across the sector. Business leaders feel what is needed now is clarity of direction, confidence in execution and the right partnerships to help insurers move from consideration to action.
“We may have legacy today,” added one attendee. “But we don’t want legacy tomorrow.”
