Pros: Good pay, some great people, and an interesting problem set. There is much that needs to be done to modernize the tech stack and many interesting challenges to work on, if you happen to get a leader who is able to see this and empower you to take them on.

Cons: Leadership is a real mess at Twilio. Constantly shifting priorities, infighting, politics, lack of vision, and low levels of technical understanding are all blanketed with a lack of awareness of these weaknesses. The company was oriented around growth, and when that suddenly stopped being the focus, it ended up destroying its culture to try to adapt to the changing market. Silos that were marginally annoying in 2021 turned into WWI-style entrenchments in 2023, where directorial fiefdoms prevent any sense of community or the ability to collaborate outside the scrum team.

Pros: Got me to where I am during some difficult times.

Cons: Twilio engineering has a tendency to flag in the wind at times.

Pros: Great team. The company was really supportive in general, and especially during COVID.

Cons: Extremely quick growth disrupted all the processes inside the company. It had to reinvent itself, which is tough for employees, as it caused a lot of chaos.