In this episode of Cards Against Complexity, we speak with Adrian McDermott, Chief Technology Officer at Zendesk, about how large-scale enterprises are navigating service transformation in the era of generative AI. Drawing on Zendesk’s journey and his own evolution as CTO, Adrian shares actionable insights for technology leaders operating at enterprise scale.From shifting organizational models to integrating AI across customer touchpoints, this conversation examines the realities of digital transformation in complex service environments.

Key Takeaways:

• Leading Enterprise Service Through AI Transformation:
Adrian outlines how enterprise customer service is being redefined through AI—moving from ticket handling to true resolution platforms. He explains what it takes to deliver end-to-end outcomes at scale, especially in large retail and financial services organizations.

• The Strategic Rise of R&D in the Enterprise Context:
In a rapidly evolving AI landscape, Adrian highlights why R&D must move beyond feature execution and into research-driven innovation. He explains how this mindset shift is critical for enterprise product teams to stay relevant and responsive.

• Practical Advice for Enterprise CTOs:
For technology leaders in complex, often non-digital-native enterprises, Adrian emphasizes starting with clear business problems, building realistic AI applications, and strengthening foundational systems like APIs, documentation, and agent tooling. “AI doesn’t replace the basics,” he notes—it builds on them.

If you're leading or influencing enterprise-scale service operations, this episode offers a grounded look at what AI really means in practice—and where to invest next.