I worked at Twilio from 2014-2023 and had an incredible experience during those 9 years, including all of my interactions with Jeff.
One of my favorite moments was running into Jeff in the hallway at our Beale Street office just before he had to do a quarterly earnings call after we went public. I said "good luck on the earnings call" and Jeff said thanks then asked what happened to a link to a specific Stack Overflow question/answer from one of our docs pages that got removed. He had just been building an application and felt like that answer was particularly helpful for context in a certain programming language, and was surprised it was removed.
Jeff's always been software developer at heart even though he had a ton of non-dev responsibilities. There are definitely advantages and disadvantages in that mindset! But he created a tremendous company along the way and I wouldn't change working there for anywhere else during those years.
One of my favorite moments was running into Jeff in the hallway at our Beale Street office just before he had to do a quarterly earnings call after we went public. I said "good luck on the earnings call" and Jeff said thanks then asked what happened to a link to a specific Stack Overflow question/answer from one of our docs pages that got removed. He had just been building an application and felt like that answer was particularly helpful for context in a certain programming language, and was surprised it was removed.
Jeff's always been software developer at heart even though he had a ton of non-dev responsibilities. There are definitely advantages and disadvantages in that mindset! But he created a tremendous company along the way and I wouldn't change working there for anywhere else during those years.