S1E2: Agent Talk #2: Kelly Waldher (Zendesk) - How Zendesk Disrupted Itself

Zendesk's journey isn't just another AI adoption story - it's a masterclass in how even enterprise companies can reinvent themselves in the age of AI.

While others rushed to add AI features, Zendesk took the bold step of completely reimagining their business model.

What's fascinating is how they navigated the classic innovator's dilemma: "It's one thing to understand it, it's another thing to be in it and live it," as Kelly puts it.

They didn't just add AI - they fundamentally changed how they deliver and capture value.

Think about their evolution:

* Started investing in AI years before ChatGPT

* Built global AI teams across three continents

* Developed models trained on 18 billion support tickets

* Shifted from seat-based to outcome-based pricing

While most SaaS companies are stuck in the "more seats = more revenue" mindset, Zendesk recognized a fundamental truth:

"You've got these dueling factors... seat contraction and AI arriving on the scene."

Their response? Align their success directly with customer outcomes.

It’s interesting to note that even their private equity owners, typically viewed as cost-cutters, became their biggest champions for transformation. As Kelly says

"We've got investors that are actually pushing us to go faster and to spend a lot of time on this very topic versus playing defensively."

Zendesk’s approach shows that successful AI transformation isn't about following trends - it's about solving real business problems at scale - just like with last week’s Synthesia episode.

Instead of charging for tokens or interactions, they focused on what customers actually care about: resolved support errands and tickets.

Notice how Zendesk is being a pro at handling the transition:

* starting with clear success metrics

* offering predictable pricing through commits

* and finally building trust through incremental value delivery.

This story isn't just about AI - it's about how enterprise software evolves when technology enables fundamentally new business models.

The question isn't whether to transform, but how to do it while keeping your customers' trust.

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