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Former Twitter CEO Drops by Our First Fireside Chat

2016 has been filled with many big wins for Iterable, from tripling our staff and moving into our new office in San Francisco to raising our Series B and working with dozens of customers like Yelp and Zillow to accelerate their growth.

To celebrate these successes and learn how to take them to the next level, last Friday we hosted our first fireside chat featuring Dick Costolo, the former CEO of Twitter, and David Cancel, CEO of Drift and former Chief Product Officer of Hubspot.

More than fifty individuals joined us as Iterable CEO Justin Zhu sat down with Costolo to discuss his lessons from his tenure when Twitter grew from dozens to thousands of employees, quickly exceeding what he referenced as Dunbar’s number. When the social media giant went through these growing pains, Costolo stressed the need for open internal communication with the goal of reducing perceived distance between employees and top executives.

“Make sure everyone understands what you understand,” Costolo said, emphasizing that a successful leader should promote transparency at all levels of the company. Avoiding sycophants and yes-people is also crucial, as Costolo pointed out that it is easy for bosses to be told what they want to hear, not the truth that they need to hear.

He shared how his post-grad experience with the famous comedy troupe Second City taught him how the improvisational concept of “Yes, and…” can lead to better business management. Costolo also revealed his insider knowledge as a consultant for HBO’s comedy Silicon Valley, confirming that characters on the hit show are indeed based on real-life people in the tech industry, but stated that “it’s almost never who you think it is.”

Costolo concluded by advocating for improving the physical health of a team. He believes that anyone, at any time of day, should be able to go on a hike or practice yoga, because he finds that those who do have more energy and are more productive than those who don’t. It’s no surprise that the avid Crossfit fan is now the founder of fitness startup Chorus.

Drift CEO David Cancel presents to a packed house at the Iterable fireside chat.

During the second presentation, David Cancel asserted the importance of listening to your customers. With the rise of messaging software, it’s easy for customers to provide real-time feedback, but the trick is knowing what to do with that feedback once you get it.

“People tend to focus on the wrong part of customer feedback,” Cancel stated in his slides, “They focus on the subject of the feedback instead of the root cause.” He explained that when a customer asks, “How do I do X?” the business should focus less on X and more on helping the customer get to X.

Cancel recommended incremental product updates rather than big, sweeping changes. “Every little action counts,” he said. “By using an incremental approach, you’re not just making your product better, you’re also strengthening your brand. In today’s world, helping is the new selling, and customer experience is the new marketing.”

We’d like to once again thank our featured speakers and everyone who attended the fireside chat. We’re excited to bring similar events to cities around the world, so stay tuned!

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