E353 | Scaling a startup when every customer is high-risk | Shelley Copsey

Some industries are easy to disrupt. Infrastructure isn’t one of them. But by focusing on adoption over features, clarity over complexity, and tempo over comfort, Shelley Copsey has built FYLD into a company reshaping how frontline operations work.In this episode, she breaks down the real levers of transformation: making work visible, removing friction, earning trust in high-risk environments, and rebuilding leadership as the company scales. Her insights go far beyond infrastructure - they’re a blueprint for any CEO trying to grow a company inside a resistant or complex market.What you’ll learn:🔍 The root causes of productivity breakdowns in scaling organisations🎯 How to build products teams genuinely adopt and rely on⚠️ Common failure points in organisational transformation — and how to overcome them⚡ Practical strategies for maintaining operational tempo as your company grows🧩 How to evolve leadership roles to match the organisation’s next stage🛰️ Why organisational visibility unlocks high-quality, high-speed decisionsWho should listen:Founder–CEOs and execs scaling teams, product, and operationsLeaders driving change in complex or fast-growing organisationsInvestors and operators focused on AI-enabled execution and productivityBook recommendations:Any Human Heart - William BoydAmp It Up - Frank SlootmanFour Thousand Weeks - Oliver BurkemanAbout the Guest:Shelley Copsey is the co-founder and CEO of FYLD, an AI-powered fieldwork platform transforming operations for major infrastructure and utilities companies. She leads the company’s rapid scale-up across multiple regions, helping organisations deliver safer, more efficient, data-driven fieldwork.With 25+ years across infrastructure, emerging tech, and organisational transformation, Shelley has founded, grown, and led multiple enterprise SaaS ventures. Her experience includes building GeoSLAM into a global geospatial leader (acquired by Faro), serving on the founding board of Coviu through its pandemic hypergrowth, and contributing to several CSIRO spinouts, including Emesent and PaidRight.A Chartered Accountant with senior roles at CSIRO’s Data61, PwC, and KPMG, she has completed executive education at MIT and Stanford focused on AI and innovation. Her work has been recognised by EY Entrepreneur of the Year, Sifted 100, Tech Nation Future Fifty, and Startups.co.uk’s Hottest UK AI Companies.Shelley is known for her leadership in AI adoption, scaling SaaS in complex industries, and delivering technology with real operational impact.Sign up to receive our weekly Curious Leadership newsletter:  https://subscribe.monkhouseandcompany.comFollow Dominic on LinkedIn: https://www.linkedin.com/in/dominicmonkhouse Chapters:00:02:04 - AI, Skill Shortages, and Industry Fallacies 00:04:25 - Worker Productivity and Motivation00:06:34 - Shelley’s Move to the UK and Founding Story00:08:24 - FYLD’s Growth Journey and Market Traction00:09:25 - AI’s Societal Impact and Future of Work00:11:45 -...

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