> Don't do that.
> Don't never ever EVER do that.
Why not? Is the world really going to implode because someone wants a job so badly that they slip a message into some random CEO’s inbox, an inbox that’s probably already flooded with irrelevant emails from strangers asking irrelevant things?
Don’t ever convince yourself that someone is so important you can’t email them. That’s a self-defeating mindset. Send the email and let them decide whether to ignore it, mark it as spam, block you, or whatever. Life goes on, and there are far more important things to worry about.
A judicious email to the hiring manager? Sure, why not roll the dice.
We’ve had candidates spam our every Senior+ level staff at my current job (many not even in the relevant department) trying to get their resume boosted.
Those went from candidate to rejects very quickly.
I honestly don't know if it was sarcasm or if you were serious.
At any rate, the downside of this is as follows.
The goal of having Human Resources, talent acquisition, recruiters, and other similar roles is to let hiring managers (and everyone above them, up and including the CEO) concentrate on doing their job and only assist the aforementioned roles in hiring. Of course hiring manager is ultimately responsible for hiring a good candidate but they are not expected to do things like posting job descriptions, initial screening, background checks, referral checks, employment history verification, dealing with legal stuff like NDAs etc etc, that's the job of HR/recruiters. Candidates reaching out to hiring managers (and especially higher ups) are not treated nicely by the HR as these candidates are attempting to take HR out of the picture.
HR are people and want to keep their job and get paid, and you circumventing them might be perceived as a threat to that.
That IN ADDITION to a disruption you will be causing hiring manager (or especially CEO) cause now they need to decide what to do with your email. Even though they have HR/recruiters to handle these things.
A typical result of such a "reach out" will likely be forwarding this email to HR and subsequent rejecting/blacklisting the candidate.
Edit: some clarifications
I guess the risk is that if the CEO doesn't like getting bothered and remembers your name, it might hurt your chances being hired in other ways?