Regarding dropping my oldest experience, I have already removed some of it and any dates for college. The issue I am running into is I spent 10 years at my oldest job and had a lot of great experience and accomplishments there. Because I started as a contractor there, I think I can move the start year up by two years. Dropping my oldest job would mean I only show 8 years of experience, which might be a good thing for lower level jobs but also takes away half my measurable accomplishments and some of my experience with specific skills
My other problem is my last two jobs, which I held for only about two years and one year, did not produce much that looks good on a resume
My most recent job was a bad situation. The actual job was quite different from the job description and what I was told during the interview process. Management actively prevented me from using good quality practices and was unwilling to change even when I presented regulatory requirements that required a change. (I know it’s best to avoid rocking the boat; in hindsight, I think my mistake was not going over certain people’s heads about failures to meet regulatory requirements.)
Despite having a “senior” title, much of my work could be done by somebody with only a small amount of quality experience (and the work is the kind of experience few companies are looking for). A couple of outside recruiters have told me I am not the first person with this experience at this company.
The job before that was at a startup where I knew going in there were a lot of issues. I had a small number of good accomplishments from unusual projects, but did not/was not able to use the common quality tools and skills in the way that most job descriptions ask for.
Later this week I am going to create a resume that has a longer skills list at the top and drops my oldest job.
However, the problem I see is ATS systems already have problems with the short skills summary I have at the top of my resume. They often think it is another job. Right now, almost everything in my skills summary is mentioned at least once more on my resume, sometimes on the second page and creates an additional use of a likely keyword for a skill which may help the ATS think I am a good choice.