I haven’t really seen anyone share any of their cover letters to get feedback from others — unlike resumes…

When I say cover letter, I usually just mean the email body, although I recently started attaching my cover letter as a .pdf (depending on circumstances). Until I see actual results doing that, I think it’s best I stick to “proven” methods, right?

I kind of get why posting a resume online is much easier than posting a hire-me-please pitch. Cover letters are personal, and they’re lowkey the only edge you have over others, all else equal.

Today, I figured I’d share what worked for me because I’ve gotten a few positive replies over time. Unlike last week, this is mostly from personal experience, so the examples are specific to me. But the principles are the same.

For context, a month after starting my skydive pilot job this spring, I came across another jump pilot job. I knew mine was going to end at some point, so I decided to reach out.

Tried a not-too-generic email subject: I feel like “pilot application” or similar is safe, but also overdone. I agree enthusiastic’s a buzzword, but adding (relatively) makes it sound less braggy, to increase the likelihood of the rest of the email actually being read

“Hi X” → not “to whom it may concern” or whatever, mainly because I knew the name of the person I was sending the email to, but also because that’s just too serious.

“I saw on SkydiverDriver that you’re looking for a pilot. I just started flying jumpers in upstate New York. Because our season ends in October, I figured I would introduce myself now, should you need someone around then” → makes sense to open the email with the reason why I’m reaching out, and being honest upfront by saying I’m not looking right now, but maybe later.

“As of today, I’ve flown 34 loads, and it’s been a whole lot of fun. Figuring out how to time my runs to be able to turn the next load as fast as possible (still perfecting that one) or just (re)mastering gusty crosswind landings, all the learning takes me back to my flight training days, and I’m enjoying it so far” → this part explains what I meant in the email subject (i’m selling myself)

“I’ll have significantly more experience by the time I’m done. And I definitely would love to move back south to a warmer state, so if you have a position that opens up this winter, please, don’t hesitate to reach out” → I’m now trying to persuade them they should at least maybe keep me on the list of potential hires.

“I attached my resume for future reference” → as much as I hate corporate form, that expression does the job.

Blue skies is my go-to email signature. It just works.

[now, including a link to my Linkedin profile was too much, and I don’t do that anymore]

The P.S. section might be the secret sauce. Did you know that’s one of the most read part of an email?

I try to throw in a very specific final selling point whenever I can. For skydiving jobs, that’s usually my weight. Here, I added the fact that I speak Spanish because I’m assuming a good portion of the jumpers there do.

I didn’t expect to get a reply the same day, or even for them to reach out 2 months later.

And it’s where being upfront made sense: the future hiring timeline was clearer on both sides.

See how they also signed with “Blue Skies” by the way. It just works.

So… why am I not flying for them now then?

First, I was under contract until the end of October, not September.
Second, because honestly, I want to give other low time jobs a shot. And now that I’ve completed my first season of flying skydivers, if I really wanted to go for a second one, I think I would just run it back with the boyz at my dropzone instead of going to a new one.

I must say I did hear two weeks ago they were looking for someone, but was told to keep it to myself — which is why I’m “censoring” stuff in the screenshots. Same thing for SkydiverDriver, I’ve been asked before to not share their job posts, so I don’t.

It seems most companies straight up HATE being flooded with emails from us. That’s actually what the owner of Paragon Skydive meant in the low time pilot job alert I sent for their C206 job: he wasn’t unhappy about the quality of the applications he was getting, it was the volume lol

I hope my little analysis made sense though.

Bottom line is, for most low time pilot jobs or for jump pilot jobs at the very least, I think keeping the tone real will work better than going for the polished tone. People just assume it’s AI-generated even when it’s not because of how common it’s become.

You are welcome to copy this framework. Do try to make it as authentic as possible though, otherwise it’s going to stop working too soon. This is sort of why I can’t just breakdown ALL my emails.

Not sure what I’m sending next, but probably the research on cadet programs.

Talk soon!
— Ivan