Rob Ryan is a technology strategist and enterprise AI expert with nearly 20 years of experience helping Fortune 500 companies navigate complexity, eliminate digital friction, and create more effective workplaces.

 

His work focuses primarily on industries where regulations, bureaucracy, and operational sprawl make meaningful progress difficult.

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Rob most recently served as Head of Go-to-Market and Business Value at Workgrid Software, where he led strategy for AI-powered assistants and intelligent agentic platforms. The product broke new ground by relieving cognitive overload and supporting more focused, productive work. Before that, he helped scale LumApps through its $70 million Series C funding, building functions across product marketing, presales, and analyst relations.

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He has led or advised hundreds of digital workplace and intranet transformations. His strength lies in combining technical fluency with operational insight and pragmatic execution. He is equally comfortable in architectural discussions and boardroom debates about employee and customer experience strategy.

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Rob began his career in financial services, where he experienced firsthand the systemic barriers that slow down knowledge work. That early exposure drives his commitment to solving real-world friction at scale—with clarity and empathy.

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Death by Digital Friction is his debut book, offering a practical, grounded approach to reclaiming focus, simplifying technology ecosystems, and building environments that serve people first.