Let’s start with reasons why to become a skydiver driver:
- dropzones usually* hire low time pilots, they’re all over the country, you may have the opportunity to get turbine experience at some point, and the job is so much fun.

Some cons: it’s day VFR only so no instrument time, no night time, and no cross-country time either. Your best bet is to do one season, and either move on to a turbine DZ or switch to a completely different kind of flying that will get you to your ATP minimums.

If you haven’t crossed the 500-hour mark yet, you can still get the job at a lower total time. I got mine at 400 hours. I also know some dropzones that will hire fresh commercial pilots, but in exchange, you’d have to commit to two seasons or any other agreement.

First, there’s a course that trains and helps low time pilots get a jump pilot job. This is not sponsored, but my guide wouldn’t be complete without at least mentioning it.

To fly skydivers, you undergo “specialized” training, which can be conducted by Jumpers Away. After completion of their program, insurance providers agree “to favorably consider” adding a Jumpers Away graduate with under 500 hours to the insurance policy…

Some of their graduates have been able to find jobs with as low as 284 hours.

Here’s a list of DROPZONES THAT HAVE HIRED or WILL HIRE JUMPERS AWAY GRADS.

You’re paying for hours in a C182 so it’s not cheap.

I’ll also say I’ve come across operators that love the program, and some that do not care for it. My point is, completing the course should put you ahead of most applicants, although still does not guarantee a job.

Keep in mind not all of their graduates manage to find jobs afterwards.

Jumpers Away only have training slots for April, and dropzones are expecting an April/May start.

Assuming you want to take action now, let me show you how I would do it, knowing what I know now.

I’ll explain how to win over your local dropzone, and how I got my out-of-state job offers last season (so you can just copy me).

Do note networking — which is what I’m going to talk about — is NOT a magic button you can push to get a job offer. Experts and coaches recommend to start at least 6 months prior to needing a job for it to yield results.

A question that always comes up is how to make your application stand out.

People will tell you to “network.”

And when you ask how, they’ll tell you to just “knock on some doors resume in-hand” or “to be the airport bum. “

It’s not necessarily bad advice, it’s just frustratingly surface-level.

They tell you what you need to do, they never actually give actionable steps.

Well, I will.

Here’s how to do all of the above to get a skydive pilot job.

The problem with just showing up at the airport to “shake hands” is that you’re not always welcome. I don’t mean that in a bad way. But some operations simply don’t have the time to “entertain” you showing up unannounced.

Simple solution: announce (duh!), and bring something.

I can’t speak for every low-time operation, but for dropzones, two options.

First, buying a tandem → bringing business.

I’m sure you’ve heard pilot hiring is a lot about whether or not the person hiring you can see yourselves being stuck with each other.

When you book a skydive, you have up to an hour to do that.

If you can show your prospective employer and coworkers (the guy that’s going to jump with you, the person at the front desk) that you’re not too bad to have around, you’re effectively standing out.

Maybe don’t start with “I’d love to fly for you” though. Have genuine conversations, show interest in the sport beyond time-building.

I’m sure there are ways to trick your way into the job if you’re just in it for the hours, that’s all yours to research but I wouldn’t recommend it.

Now, tandems go for upwards of $250.

Quite expensive for just a “chance” at getting a job, right?

The second, more affordable option is buying beer → bringing a gift.

Skydivers like beer. They have some sort of tradition where for each first/memorable event, the person has to buy the dropzone a case of beer: first solo, landing off-property, first tandem, buying gear…

This season, a guy followed the advice of just showing up and dropped by the dropzone during a pancake breakfast at the airport. If you don’t know what that is (I didn’t), it’s just a get together at the airport. Great time to network because a lot of pilots will be there.

That’s what the guy wanted to do. The main thing he could have done better is bring a case of beer with him.

On pancake breakfast days, the airport is swamped. We don’t really want to let in the building anybody who wants to “talk” when it’s that busy, so he just left his resume, and we didn’t even get to meet him…

→ picking a day where we have the space and time to discuss would’ve helped too. And if he showed up, 6-pack in hand, I bet he could’ve offered to put it in the fridge, get in and meet everybody.

Because the goal isn’t to leave a resume and check it off your to-do list. It’s to make an impression and unfortunately, I don’t think that guy did that day. At least, not on us.

The beer trick works because, not only are you showing up with a gift, it’s also a thoughtful one. It shows you’ve done some research.

This is definitely not going to be as novel or efficient as the beer trick. I’m sure you’ve shot some apps and only heard crickets.

But let me break down what I did last season to have 3 interviews in 24 hours.

No, I didn’t “know” anyone.

→ A combination of 2 things: job board (luck) and cold outreach (persistence).

I did the first interview on a Sunday at 10 AM, the second one that afternoon, and the last one the day after at 9 AM.

Two of the three interviews were secured after I saw their ads on ClimbTo350.

Shot my applications and got replies within hours to set up the interviews. I actually ended up at one of the two, and attached is a screenshot of the exact email I sent.

I would like to point out that the reason this email worked is because I didn’t use AI to write it. They said I was probably the only one. So, the method to stand out is to NOT use AI because everyone else will.

There’s even a typo towards the end.

I got the last interview because I found the front desk agent’s email, who then put me in touch with their chief pilot.

The chief proceeded to tell me he actually had 3 positions available. So if you want to get technical, I interviewed for 5 jobs within 24 hours, but whatever.

The timeline here was a lot longer.

I sent the very first email a year before, then reached out again a year later with an updated application, and got on the phone with the chief pilot a week later.

Attached are the exact emails we exchanged.

Bottom line is to just make it sound human. That’s definitely the method, as long as you have enough relevant experience.

I’m sure the fact that the Chief Pilot and I were in Miami at the same time helped as well (that’s where we were going to train).

I hope this helped bring some light on what you can tweak in your approach, to get a skydive pilot job.

If it did, I have one more thing for you before you go…

Once again, I’m going to be curating the internet for every low-time job I came across this year (Job Alerts). But instead of just sending individual emails, I’ve decided to build a community around it.

Why?

→ to facilitate the exchange of information and quality-control those paid job boards famous for recycling listings.

3 cases just from Q4…
- I got a text that this position was actually outdated (although posted on BizJetJobs)
- Someone emailed me to explain why this King Air job isn’t really worth it
- I was made aware Planesense’s requirements had shot up about double the posted minimums

Those were valuable information.

I don’t want to be the only one “in the know” when I learn of something new → a community is the solution.

I tried to use Facebook before, but there just isn’t an incentive for people to share if they’re in a “free” group.

Instead, a monthly subscription will encourage people to share.

There’s a little more to it but essentially, if you share a job before I do in the community, your next month is on me.

Furthermore, making a contribution similar to the examples above grant you points. If you rack up enough, next month on me.

But this is a work in progress, which is why we’ll only do 75 members for the first month, so we can adjust the point system, the subscription and everything else accordingly. My ultimate goal is to have the most reliable source of information about current low-time pilot jobs.

The current job board ecosystem (paying $20-25 a month just to get a link to apply for a job you know NOTHING about) did help me get a job last year. That’s why I don’t believe the whole thing needs to go.

But it could be better.

I have two big projects for The Road to 1500 in 2026, and the Pilot Job Hub is one of them.

Today is the official day of launch. Join us here.

Until next time,
— Ivan

P.S. if you don’t know what a job alert is and what I mean by curating jobs on the internet, here’s the archive of the alerts I sent in 2025.