In this episode of The Insurindex Podcast, host Ben Bolton, MD of Gracechurch is joined by Simon Doggett, Design and Product Lead at Ki, to explore how digital product thinking and user-centred design are transforming one of the most traditional markets in global insurance.
Ki, launched in 2021 and backed by Fairfax, is the world’s first fully digital, algorithmically-driven follow-only syndicate at Lloyd’s. Designed to provide brokers with follow capacity in seconds, Ki represents a fundamental shift in how underwriting can be delivered in the London Market.
Simon shares his journey from technology startups, digital transformation at ITV and Marks & Spencer, and fintech scale-ups, into the specialty insurance market – describing it as one of the last major industries to undergo full digital transformation
The conversation explores what happens when product designers and technologists enter a market built on long-standing relationships, manual workflows and specialist expertise. Rather than “disrupting” what works, Simon explains how Ki focuses on removing friction, reducing manual effort and designing tools that make brokers’ and underwriters’ jobs easier – without losing the human dimension that defines specialty insurance
Ben and Simon discuss:
- What “algorithmic underwriting” really means in practice
- Why design thinking is critical in B2B insurance environments
- How prototyping and user research can uncover hidden inefficiencies
- The challenge of translating analogue processes (like the slip) into digital experiences
- Why data visualisation and internal tools matter as much as external platforms
- How AI could reshape underwriting workflows and product development over the next five years
A key theme of the episode is talent. Simon reflects on what the London Market must do to attract and retain technologists, designers and product specialists and why building internal capability, rather than outsourcing everything, may be essential to long-term competitiveness
The discussion also looks forward. With AI accelerating change across industries, the episode considers how broker experiences, underwriting tools and even product design could evolve and why insurance has a rare opportunity to shape its own digital future rather than be shaped by external platforms.
Ultimately, this episode argues that technology in insurance is not about replacing people. It is about giving them better tools, freeing up time, reducing friction and enabling deeper thinking about risk, innovation and client value.
