This is because ATSes still use keyword boolean search rather than semantic and natural language search. It's super frustrating.

I'm working on building an ATS that lets you search for things like "experience scaling a company from 100 to 1000 people" or "product management leadership in fintech" even if you didn't put that on your resume explicitly. It's a fun challenge.

I'm looking for a technical co-founder (I'm a dev too). If anyone is interested in working on this with me, email me: robert at facet dot net.