Twilio has had an exciting fall. First, Microsoft announced Azure Communication Services, viewed as a shot across the bow at Twilio in the developer driven communications space. Then, Twilio had its first investor day in three years, refreshing investors on their trajectory. Lastly, Twilio announced the purchase of Segment, a customer data platform that signals Twilio’s climbing of the value chain.

To break it all down, we bring on Captain Twilio, an experienced investor whose portfolio features one stock, Twilio, and Justen Stepka, our frequent guest and an Atlassian and, more relevant to today’s conversation, Docker alum who has firsthand experience with Segment as a user. This is a fun conversation for anyone following Twilio, and it also adds interesting perspective on business strategy and SaaS valuations.

• 3:15 minute mark - The Segment value proposition

Segment blog on gross margins: https://segment.com/blog/the-10m-engineering-problem/

Jeff Lawson interview with Ben Thompson: https://stratechery.com/2020/twilio-acquires-segment-what-is-segment-an-interview-with-twilio-ceo-jeff-lawson/