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Adding a topline response echoing the same thing.

Been on the job hunt since October 1, and have done hundreds of applications, yet only spoken to 3 companies, and made it past the hiring manager once.

I’m a technical product manager with 10+ years and most recently was head of product at a healthtech company. It seems like none of my experience or background matters for the initial screen.

The most frustrating part has been spending time to update a resume and a cover letter to get a rapid rejection obviously done via AI. The fastest rejection I’ve received was 2 minutes.

It is at the point where the information-asymmetry between company and applicant is so high that I don’t think it is worth the time or effort to craft a customized resume and cover letter to match the job description. Not even with the “help” of LLMs.

The promise of Remote hiring now is proving to be a double-edged sword. It can be easier to get hired, but it means competing in an almost global applicant pool.

As a way to keep me occupied I’m building a personal tool to journal my work history and use the journal as a source to leverage an LLM to customize my resume and cover letter to a job description that sounds like me. Just need to keep the momentum up for both the continued job hunt and personal projects.

Though its starting to wear on me.


During Covid, I had many lively debates with my peers about remote jobs. They kept insisting that the "world has changed" and that remote jobs are the future. My anxious self struggled to understand that. I'm good at my job, but I'm not naive. I know I live in a high cost of living market that not everyone wants to be in, so the competition isn't too threatening.

But take that away, and as I mentioned, you’re now competing against the entire world. I've worked with talented people in Eastern Europe and Asia who could easily do my job for a quarter of the pay. I really don’t want to compete against that.

All the friends who moved their families to farms in Iowa to be near family and enjoy the low cost of living? I’d be terrified that if I ever lost my job, I’d have to search far and wide for one of those scarce remote positions, and there’s no way I’d get my Bay Area salary now.

Plus, now that my kids are in local schools in Iowa and my wife is deeply connected with the local extended family, there's no way I could move back to the Bay unscathed.

Have you tried just saying you're a product manager instead of technical product manager? In my experience small changes in storytelling and self-marketing can create giant shifts in how you are perceived.
Actually yes! In this case it was lazy shorthand.

Same result for the job hunt progress but persisting still.

I appreciate the feedback greatly. I’m sure there is a way to tell the story better.

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