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A client emailed me with this question:

I just applied to a job that I REALLY want and am a perfect fit for.  You can’t apply via their website; you have to apply through a third-party platform (  I did that, but with a little sleuthing, I also managed to track down the email address of the organization’s founder (it’s a brand-new organization), which is on his personal website (so is essentially public information).

Would it be stalker-y/obnoxious if I also contact him directly with a brief introduction and my cover letter and resume?  I was thinking maybe I could give the org a couple of weeks to respond to my Idealist application, and then if I don’t hear anything, email him directly?  But I wouldn’t want to annoy him, as that seems a little nervy.  What do you think?

I had a number of thoughts which are below:

How great that you found a job you’re interested in! Obviously, applying through their preferred mechanism is the first step.
Then I would definitely contact him, with a note that says something about how you are so excited by the organization and your ability to help it that you are taking the liberty of contacting him directly, even as you have applied through Idealist. You have to say also that in the course of researching the organization, you found his personal website, how you were impressed by what you found there, and it occurred to you that you could reach out to him. You hope he will review your formal application, etc.
I’d err on the side of brevity, on flattery, on you being resourceful. If it were me, I’d be impressed that you found me. If he’s not, then you wouldn’t want to work there anyway, imo.
And I wouldn’t wait for 2 weeks – I’d do it at the same time or at most a week later. You want your resume pulled out of the pile. If it doesn’t make it out of the Idealist pile, it may be about keywords or something, so make sure you are in the first group, or at least early on.

Will this strategy work or not?

Only time will tell.  I based my advice on my experience as a non-profit CEO who admired people who had the chutzpah / nerve to contact me directly. By doing so, they were telling me that they a) were determined, b) had research skills and were resourceful, c) were bold and confident, and d) really wanted to work at our organization.
If they kept on contacting me, that would be “stalkerish.” One time, though? Usually effective. If it doesn’t get you the result you wanted, you haven’t lost anything. Because you didn’t have the job anyway. And just maybe this tactic will bring you to the person’s notice even if the Applicant Tracking Software doesn’t notice you.