Is Icon Chief Pilot – East Your Dream Job?

If you want a fun, challenging civilian flying job that doesn’t involve the airlines, I just found one for you. Here’s the listing:

(Yes, I fly for Icon…part time. No, I don’t get a bonus if I recruit you. Yes, if you get this job you’ll be my boss. It’s okay, I have 8 bosses… 😉

TPN is a great resource for helping people get airline jobs, but there are some pilots who crave flying careers with a little more adventure. I’m sharing this job listing here because I think it would be the perfect fit for many TPN members. I also want Icon to do well as a company and having an experienced pilot with strong leadership skills in this job is pivotal. So, what is this job?

Icon Aircraft ( is headquartered in Vacaville, CA. Since the A5 is a very unique aircraft, and since the founder was a military pilot, the company requires all owners to go through a training course run by the company. Right now, all this training is done at one of two training centers. The first is Vacaville, and the other is at Peter O. Knight airport in Tampa, FL. ( This job listing is to be the Chief Instructor Pilot in Tampa, putting you in charge of all Icon flight training for the Eastern United States.

Per the job description, it’s a flight instructor job first and foremost. You need to already have a current CFI and enjoy flight instruction if you want to do this job. However, as the Chief Pilot, you’ll also be in charge of managing a bunch of other Instructor Pilots and Sales/Demo Pilots. Many of those are based in Tampa, but the company also has sales reps stationed around the country. This instructor force is diverse in experience and geography, meaning you’ll face interesting challenges in leadership and standardization.

Although this is an instructor job, you’ll also be responsible for helping the sales team. This means giving lots of demo flights to potential customers. Much of that will happen while traveling around the country. Some of that travel happens on airlines (so you can rack up points and miles) while some of it may include flying the A5 between locations. If you’re looking for a cushy pilot job with zero nights away from home, this job is not for you. That said, there’s far less travel than many corporate and most military and airline flying jobs. On those trips, you’ll end up getting to exercise a lot of leadership to oversee people, logistics, maintenance, aircraft, schedule, and safety.

Icon is a fun and fascinating company to work for. In many ways it feels like a startup, even though it’s been around for more than a decade. One way it differs from many startups though is that it has a lot of money. We all try to be good stewards, but you won’t be eating beans and rice in the alley behind the Motel 6 on your trips. As Chief Pilot – East, your opinion will hold significant weight and you will be able to help shape the future of the company. You have a counterpart on the west coast and you both report to an overall Chief Pilot or Chief of Flight Operations at HQ. If you’re willing to consider relocating for great employment opportunities, taking this job could definitely lead to you moving up the chain and getting that higher job in Cali. I see a potential for a great performer to go even higher in the company from there. If you’re interested the possibility of working your way into upper or even executive management in a growing company, this job is absolutely for you.

The A5 is the brainchild of an F-16 pilot who has a true vision for aircraft design and performance. It’s a pure joy to fly. I wish I could explain it better, but short of just taking you out and showing you there’s just no way. This job is not teaching stalls & falls to obnoxious teenagers in a rustbucket C-152. Although Icon always has a big presence at Oshkosh (,) you won’t find them marketing at the average FBO. They go to Lamborghini shows and have an A5 featured at a supercar dealership in Miami. ( I wouldn’t be surprised to see Icon show up at the F***ing Catalina Wine Mixer. This job is teaching seaplane operations to serious buyers, most of whom already have pilot licenses.

ICON Aircraft and Prestige Imports partnership will focus on ICON's vision to make personal adventure flying more accessible.

If you’re avoiding an airline job because you enjoyed exciting flying in the military and driving a giant bus for the rest of your life sounds terrible, the A5 will meet your every need. It’s easy to fly, but you could spend a lifetime learning to fly it well. The water flying environment is very dynamic, and I promise it will regularly find new ways to challenge you.

You may be wondering why this job is opening up. The current chief pilot (whom we’ve named Poomah) is awesome, but she’s finally reached a position where she can pursue a lifelong dream of becoming a military aviator. She’s looking at a minimum of 2-3 years of full-time military service and you’ll have some big shoes to fill. (Metaphorically that is. Her feet are actually kind of small.)

So, why am I floating this job to TPN? I’m looking for a very specific type of pilot.

Ideally, I’m thinking of a military pilot, though the right corporate or airline person could do the job too. This job absolutely demands someone with strong leadership and management skills. If you enjoy solving difficult-to-define problems and leading people, you will love this job. If you dread this loss of leadership opportunities associated with an airline job, this is definitely a great job for you.

It’d probably be a poor fit for an O-6 or above who drank a lot of Kool-Aid on active duty. You’ll be too dependent on process and other people licking your boots to function in such a flexible environment. However, it would be good for a candidate to have experience above the squadron level. You need to be able to build relationships, network, and work well with others in the sales, maintenance, and other departments throughout the company. A consummate line pilot who suffered through, yet excelled in some staff work will do best here.

The ideal pilot for this job needs to be highly experienced. It’s not enough to have a Commercial rating and 1000 hours of flight instructor time in Cessnas. I’m thinking someone with at least a couple thousand hours. Ideally, you’ll have done plenty of instruction, night, instrument, low level, and formation flying. Ideally, you’ve logged at least a few assault or carrier landings. This also needs to be someone comfortable not just with instructing, but with training, leading, and managing other instructors. The ideal person for this job will have experience as a military standards pilot, or an airline Line Check Airman.

This description fits a large portion of The Pilot Network, but there’s another set of requirements. To perform well in this job, you need to be conversant (if not fluent) in General Aviation. No, “I flew a T-41/T-3/DA-20 in flight screening a decade or two ago” is not good enough.

While this job requires the leadership, management, and standardization skills that a person can obtain in the military, it’s a 100% civilian operation. You need to be comfortable operating an aircraft with a piston engine driving a propeller. You need to be solid on VFR operations, flying from uncontrolled airports, civilian radio procedures, and the Federal Aviation Regulations. When you train customers, you’ll train them to the Sport Pilot level. The results of that final ride get reported to the FAA on an 8710 and you’ll be the one endorsing the student’s logbook approving them for LSA seaplane operations. If any of that confused you, you’re not the person I envision for this job.

That said, I suspect you’d be competitive for this job without as much depth of GA experience as I’ve suggested here. However, you should not apply for this job unless you’re actually willing and motivated learn and embrace the GA knowledge you need. If this post has you excited, but you’re lacking on GA street cred, you should go read Part 91 ( and Part 61 (especially Subpart J) ( right now. You should also rush out to your local FBO and do some civilian flying to re-familiarize yourself. These are just a couple small things you can do to help make your stars aling if you want this job. (

Surprisingly, while seaplane experience is definitely a plus for your application, it’s not required. Icon has regularly shown great discernment by recruiting for overall experience, skill, and attitude and then paying for their people to get a seaplane rating after being hired. Don’t let the fact that you don’t have this rating deter you.

This job isn’t for everyone, but if you like exciting flying, leadership, a challenging work environment, and you’re at least interested in the sales side of business, I think you’d love this job. If you think you have what it takes, I suggest you at least submit an application. Don’t hesitate to shoot me a PM if you want some more info on the job/company or other ideas on preparing for the interview.

I got excited enough to write this up because I happen to work for Icon and know about the job. This is far from the only opportunity like this out there. If you’re a military pilot looking for something more exciting than driving a bus, or you’re a fellow Canabus driver looking for a side-hustle, there are all kinds of fun and interesting flying jobs out there. Don’t be afraid to look for them. They all need motivated, experienced pilots, and leadership is always a plus. If you belong to TPN, that description probably fits you. Happy shopping!