Allison Pickens' Podcast

Scaling from $10M to $100M+ ARR: Lessons from Contentful's CEO


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I’m excited to continue the series on Growth Endurance — how to sustain high growth rates for a long time, in the face of macro headwinds. In this episode, I traded notes with Steve Sloan about our experiences scaling companies through all stages. Steve is now the CEO of Contentful — #38 on the Forbes Cloud 100 list, with over 800 employees. Steve was previously Chief Producer Officer at SendGrid, growing the company from an early stage through IPO and through its subsequent $2B acquisition by Twilio, where he became Chief Product and Marketing Officer.

Steve and I discussed how to run a company differently at $10M, $30M, and $100M in ARR. We covered topics such as:

* How do you handle malaise on the sales team when you have to increase quotas, and reps can no longer rely exclusively on the heavy inbound pipeline from the early days?

* What should you expect of executives as you grow larger, and how does the executive role differ from a functional leadership role?

* Why is your pricing model so important, and what does it take to get it right?

You can listen to the podcast or else read the lightly edited transcript of the conversation below. Let's dive in!



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Allison Pickens' PodcastBy Allison Pickens