Twilio

• A good core technology and commitment to building a business
• A strong sense of social mission

The engineering org has lost its way, and the pace and quality of innovation fell off a couple years ago and may never return.

It's become a sales company and only cares how much its reps are crushing it.

The product side has become a confusing mess of mismanagement, bureaucracy, politics, and competing sideways initiatives.

Twilio has the bureaucracy of a company ten times its size.

None of its management knows what their jobs are or how to do them.

The company has an inkling that something is wrong and is beginning to make some good firings, but the quality of incoming management is ever lower, so it's not helping.

The company is so enamored of social justice initiatives and abstract corporate values that the culture has become very cult-like and is getting in the way of them actually running a company that takes care of its people.

If you care so much about making the world a better place, then quit and go work for a nonprofit. If you care about making Twilio a better place, then ditch all the magical thinking and build a company that cares about the development of its people before everything else, including the next sale or the next product ship.