Twilio is one of the clearest examples of expansion revenue driving enterprise value. In this episode, I break down how Twilio’s developer-first GTM, usage-based pricing, and broad product catalog produced dollar-based net expansion rates of 170% in its early years, held 120–130% at scale, and sustained net negative churn for over a decade.
We’ll look at the mechanics behind usage-aligned billing, why a $20 free trial could scale into $10M+ accounts, how cross-sell into email and data shifted margins, and how Twilio’s valuation swung from $60B at peak to 3.5x forward revenue as net retention cooled.
If you’re building SaaS, this is a clear case study in how pricing models and retention metrics dictate growth and market cap.
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