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The Job Search at 55+

The standard job search playbook is calibrated for a 38 year old. Updating LinkedIn, telling everyone you are open, applying widely, working with a resume coach. All of this advice is wrong at 58, and following it actively backfires.

The standard job search playbook is calibrated for a 38 year old. Updating LinkedIn, telling everyone you are open, applying widely, working with a resume coach. All of this advice is wrong at 58, and following it actively backfires. The mechanism is simple. At 38 you are competing on bandwidth and trajectory. At 58 you are competing on judgment and fit. Bandwidth strategies surface candidates. Fit strategies require a smaller, warmer, more deliberate process.

The advice that replaces it: stop applying. The senior roles that match your last decade of experience are not on job boards, and the ones that are on job boards have already been wired to an internal candidate by the time the listing goes up. The actual market for VP and SVP roles runs through retained search firms, board introductions, and former colleagues now sitting two seats away from a hiring decision. The work is to be in front of those three channels, in that order, with a clear and current narrative about what kind of role you want next. The work is not to optimize your LinkedIn headline.

The other piece of advice that almost no one is told directly: the recruiter conversation is a screening conversation, even when it does not feel like one. The question "what are you looking for next" is not a discovery question. It is a triage question. Operators who answer with breadth ("I am open to a lot of things, I just want to find the right fit") get filed under maybe and never called again. Operators who answer with a specific shape ("a CFO role at a growth stage B2B SaaS company between 50 and 200 million in revenue, ideally PE backed") get remembered and called when something matches. The specificity feels limiting. It is not. It is what gets you on the short list.

The briefs in this category will cover what retained search firms are actually screening for at the senior level, how age discrimination shows up in real searches and how to surface it without losing the room, the resume that has become a liability and what replaces it, and the specific moves that turn you from someone applying for jobs into someone being recruited for them.

Published by:

Marc-Eric LaRocque

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