I agree wholeheartedly with that approach. You're more likely to be successful if you tailor your story and experience to each opportunity, particularly if you have 20+ years of experience.
Specifically, OP mention about applying to a "Senior engineer" and "VP of engineering". Depending on the size of the company, these are very different roles. A killer profile for one could be terrible fit for the other, and vice-versa.
This is before you customize your submission for each job.
While a "35 year career in Silicon Valley" might sound impressive to some people (and perhaps rightly so), as a hiring manager I probably don't care about any projects/technologies you worked on in 1983... I want to know whether you can do the project I need delivered now. Tell me what you worked on last year and in the last 5 years - skim over or leave out the rest.
(If you're dealing through recruiters instead of directly with hiring managers, you've got a different set of problems - the solution to which is probably ignore the recruiters and don't play that game - surely a 35 year career has left you with a network that can bypass those rent-seeking gatekeepers?)
I’ve noticed some anxious double-takes in interviews after passing hiring filters with my shorter resume.
I’ve met people who have changed careers and decided to leave off their prior career work. Resumes are used in the background check for some companies but no one looks beyond 7 years. And if they really have a problem, do you really want to work for them?
The recruiters I've dealt with usually want to slap on a bunch of crap like "Web scala Java OOP web-scale MEAN STACK" onto the resume before they submit it, but the solution to that is to do it all in LaTeX so that they don't know how to work with it :)
I found this to be true a lot of the time. Great idea to tailor your resume to the type of position you're applying for.
Several companies I’ve worked for have had a checkbox on the HR paperwork for interviews, have all gaps in the candidates CV been explained Y/N?
Edit: also want to point out that if you only have worked in greenfield projects where you could grow with the particular tools and practices of that project, you don't know anything about writing maintainable code