The Challenge of Being Opinionated

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Zandesk is a go up market company. So we start with this opinionated product. But at the same time, i think it's important to realize that one of the words we're using a lot more internally is flexibility. For youre more sophisticated, larger customers and people who just need flexibility, that flexibility should be there. You don't actually have to spoon feed people, necessarily, who are looking for flexibility. I strongly believe that. And a significant portion of our business is self service. Even our expansion inside of enterprises to multiple instances is effectively self service in some ways - although it could be assisted.

Today’s episode is with Adrian McDermott, CTO of Zendesk.

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.

Our discussion digs into the challenges that come from scaling startups. We start off by diving into a common decision point: whether to continue with what's working or try to make a change. Adrian goes much deeper than the “what got you here won’t get you there” advice you hear all the time in startups.

Next, we cover the struggle over exploring new product areas, while still continuing to make the central product brilliant, with Adrian sharing how they use the zone to win frameworks at Zendesk.

Then we dive into another classic startup dilemma: whether to build or to buy. Adrian walks us through the origin stories of several Zendesk products, from the wins to the lessons learned. In addition to sharing his perspective on the role of competition in product strategy, he also offers up his definition of a truly great product.

In the back half of our conversation, Adrian shares what he’s learned leading both product and engineering teams, as well as some of the go-to-market lessons he’s picked up along the way. We end on team building and recruiting. Adrian’s interviewed more than a thousand engineers, and shares more about how he’s approached hiring at the different phases of scale at Zendesk.

You can follow Adrian on Twitter at @amcdermo. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson