I recently sat down with Adrian McDermott, CTO of Zendesk, for a candid conversation on how to scale product and engineering without losing the essence of what makes the product great.
Adrian started at the company back in 2010, when they were only 50 employees. Since then, he’s led product management and engineering teams as the company has gone public and scaled to over 5000 employees. I’ve long admired how that trajectory blends product management leadership with operational rigor, and I wanted to unpack the systems behind it.
We began with the classic scaling fork in the road: double down on what’s working or make a change. In my experience, this decision rarely fits a simple binary, and I asked how he navigates it in practice. He went much deeper than the “what got you here won’t get you there” advice you hear all the time in startups, outlining how to read momentum, market signals, and organizational readiness before flipping a switch.
Next, we explored the tension between venturing into new product areas and keeping the central product brilliant. He shared how they use the zone to win frameworks at Zendesk. I contrasted that with my own approach to product discovery and product roadmapping and sprint planning: protect core experience quality with clear guardrails while allocating explicit capacity for bets that expand the addressable problem space.
We then dug into the evergreen dilemma of whether to build or to buy. He walked through the origin stories of several Zendesk products, from the wins to the lessons learned. His take on the role of competition in product strategy and his definition of a truly great product resonated with me. For my teams, I evaluate buy vs build decisions through a simple lens: strategic differentiation, speed to validated learning, total cost of ownership, and ecosystem leverage; if the capability isn’t core to our unique advantage, I bias to buy and integrate, then instrument relentlessly.
In the back half of our conversation, he shared what he’s learned leading both product and engineering teams, along with practical go-to-market lessons that shape how features actually land with customers. We ended on team building and recruiting. Adrian’s interviewed more than a thousand engineers, and I appreciated the way he adapts hiring profiles and loops to the phase of scale—tight generalists early, then rigor around outcomes vs output as the organization matures.
If you’re scaling a SaaS product, you’ll find actionable insights here: how to avoid false trade-offs, decide when to preserve the core versus explore, operationalize zone to win frameworks, and make smarter buy vs build calls that accelerate learning and customer impact.
As a product leader, these lessons reaffirm a simple truth: sustainable growth comes from deliberate portfolio choices, clear go-to-market alignment, and consistent, values-based hiring that raises the quality bar with every new teammate.
Inspired by this post on First Round.
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