Early Twilio engineer here. There was never really all that much unique ground breaking technology work being done, we used open source tools running on AWS to build the core products. Our differentiators were reliability and user experience. Both of those came from how the organization was built and run. There was an obsession with uptime and DevOps, with a carefully guarded culture of collaboration and blameless postmortems when things went wrong. Empowering individual engineers and product designers to call out when things sucked really went a long way, and is really hard to scale. Initially managers and directors had very little power over the actual makers and maintainers, which lead to a lot of quality. A few years post-IPO we hit a scale where a lot of that culture began to fall apart. That’s when I made my exit/was pushed out.
