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I think the market has a lot to do with it. I have heard a recruiter mention that age might be taken into consideration for contact work but nothing major that I have noticed. Start up experience is of course a plus but the market right now is just ass. One job post I saw had over 1000 applicants but let’s say even if that’s not 100% accurate half of that is still a boat load of applications for ppl to look at. And that’s not even including referrals.
The formula for resume experience bullet points that has worked for me is:
Action verb > result > brief context
I understand the "no interviews in 6 months." 20+ years of experience - some of working for well known companies and projects - and you can't even get past the resume screening. I applied to several of jobs where I met or exceeded every requirement, including the 'desired' items, and didn't hear back.
Based on your experience and "wearing many hats" it seems likely you will be able to make the transition. The problem I've seen in interviewing for smaller companies is that often they worry those coming from larger companies can't "keep up with their pace." Interviewers question your ability to adapt to their work cycles and culture. You may have to spend a lot of time in interviews trying to convince them you are a cultural fit.