Pros
Twilio is, and will be for some time, a leader in their space. The technology and the talent at Twilio is driving telecommunication to do things it is very uncomfortable doing. That being said, this a what a disruptive company looks like. They are taking a legacy industry and flip it in on its head. The Engineering talent at Twilio is unmatched and the collective brilliance is what has taken this company as far as it has gotten to this point. Working at Twilio is much like going home to family. You see a lot of smiling faces and hugs all around.
Cons
This is where "family" takes a whole new meaning. Much like a large family you have cliques, favorites, and perhaps some people get a bigger allowance because of the favoritism. The tension between teams is pretty ridiculous for a company this size and I believe there is zero empathy for what each team is going through. While each team is burdened in their own way, there is very little being done to curb or improve the camaraderie. There still exists a small group of people who have been with the company for a long time that have major influence over hiring/firing and other seemingly meaningless business decisions that impact the morale of the company. Why this still exists is a mystery, but I am sure the sense of entitlement they must feel every day is somehow gratifying in their day-to-day work life. These people are often untouchable, unapproachable, and condescending to deal with. While the engineering talent is tremendous, it's difficult to understand why so many failure points exist. Issues that are usually brought up after a big issue are rarely followed up leading to instances where the issue pops up again further impacting customers needlessly. A lot of focus is around what new features people are working on with very little thought around fixing existing infrastructure beyond the hyperbole people hear in group meetings. One thing that also stands out is that people are pushed out of this company far too often. Good people. People with great ideas but those ideas may not align with the company gameplan so their jobs are made difficult until they decide they just don't want to take it anymore and they leave on their own or are simply just let go for very little reason. Bottomline: if this company wants you out, they are going to find a way. But just to be fair, this is true for most companies in the Valley.