So true. CTO being so far upstream, mistakes made here through disconnection between the rubber and the road have compound effects downstream. It's the sort of role where bad decisions have huge, company-ending ramifications.
"I talked to my buddy at [FAANG] and he said microservices are the way to go. His team achieved awesome velocity by switching to microservices. Let's do it guys!".
Amazon had huge dependency problem, both technical and organizational. Technically, the effort to work in their monolith scaled superlinear with respect to the CL size due to coordination and review with other teams. Organizationally, teams were dependent on an ever growing set of centralized, global processes that further slowed their ability to make progress.
Jeff (and S-team) saw these issues and worked to solve them through a series of experiments. Specifically, Jeff tasked his then CIO with finding a solution. This CIO worked throughout the organization to gather on-the-ground feedback around what was and wasn’t working; built a model for how Amazon _should_ work based upon that sense making; and then tested, iterated, and refined that model into what we’ve come to know as Single-Threaded Leaders and Two-Pizza teams, etc., today.
In parallel, a couple Amazon business units were experimenting with exposing their data via textual (XML) APIs like the Amazon Associates API which went on to become the Amazon Product Listings API. These early APIs were sort of the POCs that allowed Amazon to see early validation around the concept of web services.
Synthesizing all these different streams of information, ideas, and actions lead to Jeff’s “edict” around building standalone web services (which eventually led to what we know as AWS today).
In short, Jeff is the exact antithesis of GP’s straw CTO. He speaks from data, facts, and information gathered from a myriad of internal and external sources, not merely anecdotes of success from a CEO buddy. :)
Source: Working Backwards has a lot of information on Jeff (and Amazon’s) decision making.
While a CTO needs to have grown up in the technical trenches to have credibility, a CTO should not be making any technical decisions anymore. If they are, that's a red flag for a CTO who can't let go and keeps micromanaging.