380: Customer Service's AI Shift: Zendesk CTO Adrian McDermott on Deterministic AI and Context Engineering

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Adrian McDermott is Chief Technology Officer at Zendesk, where he leads the company’s product management and engineering teams and helps shape the technology behind one of the world’s most widely used customer service platforms. He joined Zendesk in 2010 and has played a key role in guiding the company’s product and platform strategy as customer experience continues to evolve in the age of AI. Drawing on years of experience building enterprise software used by service teams around the world, Adrian brings a thoughtful perspective on how AI can help organizations deliver better customer service while allowing people to focus on the work humans do best.

In this conversation, we discuss:

• How customer service evolved from a cost center with rigid scripts and binders into a strategic function where technology helps teams deliver better experiences. • Why customer service leaders shouldn't fear automation — and why everyone has a "service debt" that AI can finally help pay down. • The shift from traditional contact centers to AI-enabled service platforms that help companies respond faster while improving both employee and customer experience. • Lessons Adrian learned scaling Zendesk from a small product team to a global platform serving 100,000 customers and how product-led growth shaped that journey. • The critical challenge of moving from non-deterministic, creative AI models to deterministic, reliable solutions necessary for enterprise trust and safety • The future of context engineering and why the next major leap in AI won't be about superintelligence, but about building systems that capture and act on the knowledge created in every customer interaction.

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Subscribe to the AI & The Future of Work NewsletterConnect with Adrian on LinkedInAI fun fact articleOn How the impact of the pandemic on leaders, culture, and the evolving nature of work