at what point can i have a 2 page resume? or do i keep removing past experiences and only keep the recent 3-5 companies with a handful of bullet points?

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The 2-page is just a guideline. If the applicable experience and explanation of your skills and achievements takes more than 2 pages, so be it.
Concentrate more on keeping your audience interested, giving them your strongest points at the beginning, and avoiding generalities that sound like boilerplate statements.
On the other hand, it is ok to just keep a reduced list of companies, if your experience extends more than 20 years (my rule of thumb). The experience they are most interested in is up to 10-15 ago.

Listen, I know everyone says keep your résumé to one page but if you have a valid and important experience and other impressive traits that requires two pages I say go for it. I know that I have two pages for my resume. I never had a problem getting a call back and when I was recruiting two pages never scared me away as long as it’s valid experience, 3 to 5 years is still relatively new once you get to the eight to maybe 10 your range you can start dropping it off but don’t sell your resume short just because everyone says oh it has to be one page.

One page is typical for college or entry level folks.

Two pages is the norm.

Anything more is for seasoned applicants who have a story to tell.

Length is not as important as CONTENT (results, metrics, impact, etc)

If your resume is 2 pages or more and all you've done is listed job responsibilities, then you're not setting yourself up for success in this market.

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