Pros
Jeff, the CEO, tries fairly successfully to build a different kind of company. Think all the things you know and hate about big companies, he wants to avoid these. There is a strong emphasize on creating a family atmosphere: Twilio-Birthday parties, ThanksGiving dinners, Halloween costume contests, volunteering as a team and many more year round events. If you haven't yet realized the product is awesome and Twilio grows like crazy. There is also a strong desire for cultural diversity. If you always felt you are different from others, maybe even considered by some a little weird there is a good chance Twilio will hire you and you will have found a family at work. There is a lot of tolerance here. They hire almost only young people though, so be aware of that as well. People are trying hard to-do-the-right-thing beyond their jobs. Twilio for some is an attitude, an aspiration to make the world a better place ( Twilio volunteers, sponsored Hackathons, Twilio Fund, the Polaris project etc. )
Cons
Jeff is a product person, an engineer. Engineering and product teams rule this company. I think Jeff also understands the value of support, albeit the support team is constantly overworked. They have tens of thousands of signups per month and these people want to be nourished and no matter how good the Tech Support leader is and how fast they hire they will always be behind. This is an API, not a product and as such many support questions tend to be very involved. GA and Sales is outsourced to the COO who tries to operationalize his value by introducing former colleagues and corporate rules from much bigger companies. GA ( HR and Finance ) are the same as everywhere. It's a big well oiled machinery. They have their rules and processes and do their work. If you are in Sales you are pretty much screwed at Twilio. Sales strategy so far has changed every 6 months without measurable impact and they went through several leaders in the last couple years. The problem is that while Twilio is growing like crazy it does that without measurable impact by sales. For Twilio sales is a experiment and costly at that. There had been quite some attrition in the sales team lately. I think these had been pretty good people who made or were close to making their numbers. They just realized that there is no career progress in a company where a sales person is shown as Bozo the clown. Going back to the title of my review: If you want to join as support person you will either break or you turn into steel and can get a job anywhere after your Twilio life. If you want to be in GA ( HR, Finance etc.) Twilio is like any other place. Enjoy it while you are there and then move on. If you want to be in an engineering or product role at Twilio this will be the job you will rave about for the rest of your life. If you play with the idea of a sales or sales support role you are in for a surprise and you better keep your current network close at hand.
