The New York Times

Great people who care about the company. An awesome, respected brand. Reasonable benefits. An awesome place to work on your skills.

Vapid promotion path for technical roles. Hyperscale has a highly variable experience depending on the team. Teams operate in silos, and interdependence is managed poorly. Editorial vision interpenetrates everything, sometimes to a fault.

The Times is still very much an organization in the middle of a huge transition. It's understandable that there's still a lot of tweaking to be done in structuring the tech departments, and great strides were made during my time there. That said, there's still a long way to go before the organization is truly "agile."

Too much pressure is put on development managers who work directly on teams in technical roles alongside engineers. More could be done to alleviate the burden of meetings and planning on these roles to allow them to focus on product quality, especially testing and quality assurance. Mid-level management is far too focused on rubber stamps and outdated heuristics of product quality. Time to market is atrocious due to all the various management approvals that good continuous integration practices could obviate.

The summation of these problems leads to a lack of oversight, resulting in "stay safe" management practices that greatly impede innovation. Managers who are risk-adverse (to a fault) seem to be placed in charge of the most ambitious projects and get the most resources. This contributes to a brain drain on fresh talent; a lot of the best leave the quickest when their opportunities to learn and innovate are exhausted by the red tape.

A little more direction from the top wouldn't be a bad thing! It's okay to demand that effort be put into certain things that help everyone... at least make sure that teams are making progress towards sound documentation and decent test coverage.