Personal reflections and career advice

On this episode, I speak with Nick Kenn, interim Chief Product Officer at Winmau, the world's leading darts brand. Nick's career spans companies such as Betfair and Redbubble, and he now operates in interim and advisory product leadership roles across private equity and venture-backed businesses. He's now on a mission to hit the bullseye and revolutionise a traditional sport with a new, fully digital experience.

We cover a lot, including:

• Digitising a traditional sport – Building a connected darts experience requires blending physical play with digital layers like tracking, stats, and online competition without losing the tactile essence of the game
• Balancing heritage and innovation – Introducing new product experiences in a 100-year-old brand demands careful alignment between modern features and long-standing identity
• AI as a pragmatic tool – Rather than chasing trends, AI is applied where it adds clear value, such as computer vision for scoring and an AI referee for dispute resolution
• Focus over experimentation – In a high-pressure delivery environment, prioritisation matters more than exploring every new technology or idea
• Building inside a non-digital organisation – Establishing product thinking in a manufacturing business requires translation, education, and patience on both sides
• Hardware and software alignment – Unlike pure software, product timelines are constrained by manufacturing cycles, creating hard deadlines and forcing disciplined execution
• Hiring for passion and proximity – Teams perform better when they have genuine interest in the product domain, especially in consumer experiences tied to physical interaction
• Differentiation through awareness – Deep competitor understanding is essential not for copying, but for identifying where to stand apart and create unique value
• Private equity vs venture dynamics – Product strategy shifts significantly depending on ownership model, with PE favouring speed and certainty, and VC allowing more exploration
• Book smarts and street smarts – The most effective product leaders combine formal knowledge with real-world experience, adapting frameworks to context rather than following them rigidly

... and much more.

Nick mentioned an article I wrote about fractional product leadership - you can check it out here: https://oneknightinproduct.substack.com/p/the-ultimate-guide-to-fractional

• Winmau: https://winmau.com
• Winmau careers: https://winmau.com/pages/careers-with-winmau

• LinkedIn: https://www.linkedin.com/in/nick-kenn/