I’m near 50, have a tech sales job, and have been constantly miserable for the past year and a half, to the point where I’m a doctor appointment short of being officially clinically depressed. A decade ago I was an engineering director at a local company (I’m in Europe), but left due to an acquisition and joined a major tech company for a pre-sales gig that pays well, but has become a major source of frustration due to the company’s money-grabbing ethos.<p>I have deep systems, networking and hardware expertise, deal with cloud services on a daily basis, have a live (weekly updated) GitHub profile with the stuff I still build, know my way around data pipelines, etc.<p>Every time I interview at a startup for a tech leadership role (and I’ve gone in several times, after jumping through various kinds of hoops/evals/screenings) I’m cast as “too corporate” as soon as they lay eyes on me on an age/background basis alone, and it’s been driving me insane.<p>I want to go back to Engineering and am willing to take a pay cut so that I can actually help people build stuff again rather than bleed out in meetings, and I just can’t figure out how.
Don't apply for leadership positions.<p>The entry point into startups is part time advisory roles.<p>Mail the CEO/CTO directly and talk about your experience and that you are looking for a part time advisrory gig.<p>Whether it's 4 hours a week or 20 hours a week (to work on a specific problem). Focus purely on the problem and make a serious contribution to solution. Don't blame anyone or expect anyone other than yourself to own it. Avoid giving people lectures on how things worked in thousand man orgs (the time for that will come later). Just get the problem fixed. Once you do this you are in. They will automatically pull you in and expand your roles and responsibilities over time.<p>Key is to get your foot in the door and make things happen for them.
Keep interviewing - if you have the chops you say you have, you'll come across the right situation sooner rather than later. There is too much of a talent vacuum for good people to sit on the side lines for too long.