Navigating Opportunity: Whitney Gates on Aviation, Adaptability and the Power of Saying Yes

Whitney Gates didn’t expect to end up in charter sales. If you had asked her when she was 18, fueling planes at the airport in Bloomington, Illinois, she probably would have told you she was going to be a pilot. However, as Whitney’s 30-year Pentastar career proves, sometimes the best routes are the ones you don’t plan for.

We sat down with Whitney to talk about her career, her perspective on the role of women in aviation, and how her journey continues to evolve.

Q: How did your career in aviation begin?

Whitney: My grandpa was a Liberator Captain in World War II. I knew my strength in math could be applied to flying, and I liked to travel – so flying made sense. I went to the University of Illinois Institute of Aviation and earned all my ratings.

I came to Pentastar right after graduating from college. I was hired as a Customer Service Representative (CSR) in the FBO but was quickly recruited to be a flight attendant. That evolved into flying for nine years, becoming Chief Flight Attendant and Manager of Inflight Service for one of the “Big 3”, and then stepping into flight ops after my second daughter was born.

Later, I worked in operations, resigned for a few months and then Pentastar recruited me again for charter sales. I didn’t plan it, but it has turned out to be my favorite role!

Q: You’ve worn many hats over the years. What’s been the common thread?

Whitney: Whether I was fueling planes at 18, working as a flight attendant, in operations or now charter sales, it’s always been about serving people — the customer service thread runs through everything.

When I sell a trip now, I understand every part of what’s happening — the fueling, the parking, the flight attendant’s job, the pilot’s job, the operations side — because I’ve done it all. Charter sales is more technical than people think. It’s about knowing the different aircraft capabilities, delivering the best service, and constantly problem-solving. Whether it’s planning and finding special catering in a remote place or coordinating schedules and duty days with operations, I’ve been there and get it, and know that it all makes a difference.

Q: What advice do you have for women looking to break into aviation?

Whitney: Take the first step. Dip your toe in the water. You don’t have to have it all figured out. I thought I’d fly every day for the rest of my life, but if I were doing that now, I wouldn’t be happy — I want to be home with my kids.

You can keep learning as you go. I earned my dispatcher’s license long after my pilot ratings. Don’t get stuck thinking you have to know exactly what you’re going to do for the next 10 years. You’ve got 50 more after that. Try something, then try something else. Don’t be afraid to do things that make you feel uncomfortable.

Q: Have there been women who inspired you in your career?

Whitney: Kellie Rittenhouse and Kris Mayle are absolutely two of the women who have inspired me. Kellie and I started working together when I was eighteen – I fueled airplanes, she sold charter at an FBO in Bloomington, Indiana (BMI). She’s fearless, smart, determined and has done so much in this industry. Kris Mayle was my boss back when I was Chief Flight Attendant. She is very level-headed, hardworking and smart. Both ladies are great examples of people who took their experience in different directions and were highly successful.

I also learned a lot from the flight attendants I worked with when I was younger. They taught me how to be there but not be seen, how to handle difficult situations with certain pilots and how to stand up for myself. Back then, there wasn’t catering readily available or the level of additional support like we have today — we did everything ourselves. Those early corporate flight attendants were industry pioneers — thank you Judi and Brigitte!

Q: How do you see the role of women in aviation evolving?

Whitney: Honestly, I don’t ever think of it as male versus female. I started as a pilot, which was a traditionally male role. I definitely had to outperform my male classmates to pass my check rides – even with female examiners!  Although frustrating, it just makes you that much better. On the flight line at BMI, they busted my chops every day — but it made me tough. You come out of these trying situations and you’re not afraid of anything.

I do think the industry is shifting, though, with more women coming in. The key is having people skills and tenacity, which is true across every industry, not just aviation. My personality and expertise help sell our charters — we’re a premium service, and I still sell a lot of trips because people trust me, not because of the price point. It’s about building relationships and solving problems. They know I’ll be around before, during and after the trip to handle any issues.

Q: What’s the most rewarding part of your work?

Whitney: Being part of people’s big moments is incredibly rewarding. We’ve flown wedding parties, families to Mayo Clinic for medical treatment, and picked up surrogate newborns during COVID, flying them home when the airline flight could have been risky or even deadly. Once, we had the honor of flying a family to meet their soldier coming back from Afghanistan who passed away in the line of duty. You don’t ever forget those trips.

You end up being part of their “family” for the long term. Some of my charter customers were my clients when I was a flight attendant. It’s full circle. It’s a lifetime commitment, and I love being part of that.

Q: You’ve spent 30 years at Pentastar. What keeps you here?

Whitney: I bleed blue. Pentastar truly is family. They’ve stood by me through some tough times, and I’ve been able to be successful because of that support. They offer the kind of trust and management style that makes me loyal.

Q: Any final advice for the next generation?

Whitney: I can’t stress enough that relationships are everything. We’re in the business of solving problems, and it’s those connections that help you find solutions when things go sideways. Whether you’re booking a flight or dealing with a mechanical delay in the middle of nowhere, it’s not just what you know but the people you know who make all the difference.

Transparency. If the situation deteriorates, just be honest about what’s going on and how you’re going to recover. If you can’t recover, admit it and figure out how to help them from there.