Twilio

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.

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.

Stop the siloing. Finish projects that have been started. Recognize that you have to be able to say “no,” or the technical debt is going to crush everything and say “no” for you.

As a company, you’ve forgotten that your employees are people and not “resources,” and that working together creates more value than working as isolated drones, even if it means you may have to support your decisions a bit more… or even (gasp) compromise with your teams.