I wonder if you would need to expose each command as its own tool. Might be able to expose a single tool with a description and context on how to discover and call commands therein?

For how to work with command line tools built with System.CommandLine e.g. built-in commands, conventions for args and options?

May want to take a look at Brave and Arc

Totally! The key is framing improvements in terms of business value- revenue impact, conversion rates, retention. "Better search relevance" isn’t compelling; "X% increase in purchases due to Y% improved relevance" is, with experimental results to back it. Make it about outcomes.