In this episode of Beyond the Desk, host Mark Thomas is joined by Jonathan Fletcher, currently an Operating Advisor for mid-market private equity firm Abri, and former Group CTO of both CFC and Hiscox.

Jonathan takes us right back to the beginning – from tinkering with a Commodore 64 as a kid, to a split degree in computer science and music, through early jobs at Saatchi & Saatchi and the London Stock Exchange, and on to seven years scaling Hiscox's technology function. He then shares what it was really like joining CFC as employee number 200, scaling its tech and data capability to nearly 200 people, and living through one of the biggest private equity valuations the insurance sector has seen.

Now working as an advisor across a portfolio of PE-backed businesses, Jonathan reflects on what value creation really means for technology, why resilience is the number one executive skill, and what it takes to make the leap from hands-on technologist to commercially-minded leader.

In This Episode You'll Learn

  • Jonathan's unconventional route into tech – splitting his degree between computer science and music, and early jobs at Saatchi & Saatchi, a VC firm, and the London Stock Exchange
  • The seven years he spent at Hiscox, rising from architect to Group CTO
  • What it was like joining CFC as employee number 200, and the culture shock of moving from a FTSE 100 business to a founder-led, entrepreneurial scale-up
  • How CFC's tech and data team grew from 18 people to nearly 200, building in-house capability from scratch
  • What it's really like working inside a private-equity backed business, including being part of one of the biggest ever PE valuations for an insurer
  • How his role evolved from hands-on engineering to a more product- and business-facing leadership position
  • What his current advisory work with Abri and non-exec role at AA Ireland involves
  • Where AI and automation are already reshaping specialty insurance, and why identifying 'who a company really is' remains one of the hardest unsolved problems
  • His advice for technologists who want to move into senior leadership roles


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Connect with Mark Thomas and Jonathan Fletcher on LinkedIn to continue the conversation.

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