I worked at Twilio from 2011 to 2022, and it was quite the amazing ride, especially for the first four or five years. Twilio basically wrote the book on API-first businesses, and on how to court developers to use and love a product, and evangelize that product to less-than-technical management types. While Jeff wasn't all that involved in the technical side of things by the time I joined, he still kept his engineering chops up, and it was always fun to see him live-coding Twilio apps on conference stages.
I was disappointed in Twilio for the last several years I was there. What had started off as an engineering (and product) focused company devolved into being driven by sales. We put out some products that were half-baked from an engineering perspective, and it showed: missing or buggy features, downtime, and unfulfilled promises to customers that sales/product made with barely perfunctory consultation with engineering. IMO it really hurt the company's reputation. I remembered a time when mentions of Twilio in tech circles would come with praise and even awe; more recently complaints seem to have overtaken the good vibes.
The "Ask Your Developer" billboard on US-101 as you entered SF was iconic. I loved that billboard; it perfectly encapsulated what the company stood for and illustrated why I was so happy there. For a while it was changed to something about reducing customer acquisition costs, a big red flag. More recently, it says some meaningless nonsense about "digital greatness" and "customer AI". That kind of shift tells me everything I need to know about where things have headed.
Ok, time to stop being so negative... having said all that, I wouldn't trade my time there for anything. I learned more than I thought possible, worked with a ton of people who I respect heavily, made many lifelong friends... it was a life-changing experience. Jeff was a big part of that, and I'll always be thankful to him, Evan, and John for creating a place where I could thrive and grow.
I was disappointed in Twilio for the last several years I was there. What had started off as an engineering (and product) focused company devolved into being driven by sales. We put out some products that were half-baked from an engineering perspective, and it showed: missing or buggy features, downtime, and unfulfilled promises to customers that sales/product made with barely perfunctory consultation with engineering. IMO it really hurt the company's reputation. I remembered a time when mentions of Twilio in tech circles would come with praise and even awe; more recently complaints seem to have overtaken the good vibes.
The "Ask Your Developer" billboard on US-101 as you entered SF was iconic. I loved that billboard; it perfectly encapsulated what the company stood for and illustrated why I was so happy there. For a while it was changed to something about reducing customer acquisition costs, a big red flag. More recently, it says some meaningless nonsense about "digital greatness" and "customer AI". That kind of shift tells me everything I need to know about where things have headed.
Ok, time to stop being so negative... having said all that, I wouldn't trade my time there for anything. I learned more than I thought possible, worked with a ton of people who I respect heavily, made many lifelong friends... it was a life-changing experience. Jeff was a big part of that, and I'll always be thankful to him, Evan, and John for creating a place where I could thrive and grow.