Flying High Together: Celebrating National Siblings Day with First Officers Sydney and Jeremiah Harper

In honor of National Siblings Day, we’re highlighting a truly special bond that soars above the clouds — literally! Meet Envoy First Officers Jeremiah Harper and Sydney Harper, a brother-sister duo who not only share family ties but also a passion for aviation. From encouraging each other through flight school to now soaring across the country as professional pilots, their journey to the flight deck is one of support, teamwork and shared dreams.


What made you want to become a pilot? Did one of you influence the other?

J: In high school, I took an interest in aerospace engineering. I took classes and studied the topic throughout school. During my senior year I was given the opportunity to experience a flight in a Piper Archer. After a tour of Dallas and performing some flight maneuvers, I decided that I would like to pursue a career in aviation as a pilot.

S: I had an opportunity to go on a discovery flight around Dallas. I remember it being a beautiful blue-sky day with a few light clouds. Looking out the window and being level with the clouds — I was hooked! My brother started flight school before me and his ability to fly home for a quick visit did influence my interest looking into aviation.

Where did you do flight training?

J: I completed my flight training through Coast Flight Training. After acquiring my certificates, I instructed at Skymates Flight Academy.

S: My journey started at the end of my high school year as I was working on my Private Pilot’s License (PPL) part-time while in school. After finishing up my PPL I did the remainder of my training at Coast Flight Academy. We instructed at Skymates Flight Academy before joining Envoy together.

What made you choose Envoy?

J: I chose Envoy because it was recommended by my mentors from the American Airlines Cadet Academy. My sister and I always wanted to work at the same company. We went to the same schools to train and instruct and are lucky to be able to be professional pilots at Envoy together.

S: Envoy was highly recommended to us both, and I had always looked forward to working with my brother.

What’s your favorite part of the job?

J: My favorite part of the job is landing the plane. Being able to get a perfect landing in just makes my day.

S: My favorite part of the job is a combination of learning a new airplane and landing. Landings are always changing and are different than the one before. 

Can you speak to the quality-of-life aspect of being a pilot at Envoy?

J: Work/life balance is supported and encouraged at Envoy. The company provides numerous lines that pilots can bid for to support their personal schedules and quality-of-life. On the job, the company provides us with well-maintained aircraft to operate. Envoy pilots are professional and take pride in teamwork to achieve getting passengers to their destinations safely and efficiently.

S: I have enjoyed working at Envoy and benefitting from the quality-of-life perks for pilots. Envoy has great pilots to work with, and guidelines to work together for safe and smooth flights.

What’s your best advice for other aspiring pilots?

J: Being able to see the world from the flight deck for the first time in an Archer, only made me crave to see more of the world at greater heights. Becoming a pilot requires determination and discipline, but being able to cruise over cities and landmarks makes it well worth it.

S: My advice would be to just go for it. If someone inspires you, then lean into it!

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