Episode #59 | Stuart Winter-Tear | From hype to stewardship

The Only Constant

In this episode of The Only Constant, Lasse Rindom speaks with Stuart Winter-Tear, a sharp voice in the AI space known for balancing enthusiasm with critical insight. Their conversation tracks the evolution from generative AI hype to something more measured, thoughtful - and ultimately more valuable:

• Why real transformation won’t come from flashy demos, but from deep integration into workflows and systems
• The risks of treating GenAI as a strategy rather than a tool, and the importance of grounding AI in real business needs
• The growing tension between innovation speed and security, and how enterprises are re-learning old lessons too fast to apply them
• How “shadow AI” and sycophantic AI models are creating both hidden risks and unexpected human dependencies

This episode isn’t about AI optimism or pessimism. It’s about realism. As Stuart puts it, we may all end up stewards of AI systems - whether we’re ready or not.
Do you want to know more about Stuart Winter-Tear?
Stuart is an accomplished Product Leader with 20+ years driving innovation across AI, Cybersecurity, eCommerce, and SaaS. As a fractional CPO, advisor, and consultant, he partners with ambitious companies to scale smarter, innovate faster, and bring cutting-edge products to market. He has founded and grown ventures, led cross-functional teams in both startups and enterprises, and delivered patented AI solutions that transformed adoption, automation, and growth.
Known for combining deep technical insight with strategic clarity, Stuart specialises in product innovation, go-to-market execution, and aligning AI capabilities with real-world business needs. As an Ambassador at the Centre for GenAIOps and a frequent speaker and writer, Stuart is at the forefront of AI evolution - committed to helping teams build ethical, impactful, and market-leading products.