Last time I was job hunting I did something similar: Write out everything I've done, even "silly" things like Haskell knowledge from uni, then comment out everything not relevant to a job until my resume fits on 2 pages. My Latex Template made this much quicker than it sounds, maybe ~10 minutes per application (and 10+ hours to create the CV itself...).
Two issues I see that haven't been mentioned yet:
1. A lot of companies, especially startups, are fake job advertising. They want to look like they are growing, and they might hire a golden goose, but many job ads I saw just stay up for months or even years.
2. A lot of companies, especially large ones, are using AI to pre-screen CVs. So you now have to get through AI, then HR, then a technical manager, each with their own sets of requirements. I've played around with some of the HR AIs, they tend to be quite... superficial. To give one example from the CV above:
> Ran small A/B tests and collected human-in-the-loop safety ratings to calibrate thresholds and escalation rules.
Is a perfectly good sentence, but according to AI should be:
> Optimized escalation rules and safety thresholds by conducting A/B test collecting human-in-the-loop safety ratings, reducing false-positive escalations by 15%.
Put your achievement first? Good. Strike out verbs like 'small'? Fair, it is a sales situation. Make up numbers entirely to provide a 'quantifiable result'? Complete crap. But it seems to be what every HR bot really wants to see, so now you have to sprinkle it in and hope it gets you past the bot, and doesn't make the technical manager think you're a complete charlatan.