Meet the Team: Willis Orlando

Jul 5, 2023

4 min read

My team is so incredibly passionate about getting members great deals and sharing their own passion for travel, and everyone genuinely enjoys working together.'

Tell us about you! (Where are you from, hobbies/interests, things you do outside of work!)

I was born in Queens, raised in Woodstock (yes, that Woodstock), NY, and now live in the beautiful, walled city of Lucca, Tuscany, Italy, with my wife, daughter, and dog. When I'm not working, I love traveling (32 countries and counting!), hiking, cooking & eating, watching and being repeatedly disappointed by my New York Mets, and soaking up the sunshine in a park or at the seaside. Nothing makes me happier than finding a sunny spot with a nice view, partaking in some snacks, and spending time with my family.

What does a Manager, Product Operations do anyway? How did you get into Product Operations?

As the Manager of the Product Operations team, I'm responsible for ensuring our amazing team of Flight Experts has everything it needs to get those tantalizing deals to our members and that Going's deals maintain their signature high quality. I'm constantly pouring over data to see what deals we can expect to see, which deals our members are looking for, and how we can more effectively help our members get where they want to go.

While I have prior experience as a Manager in hospitality and nonprofit work, I came to Going as a Flight Expert. Since then, I've put in the time to learn everything about flights, deals, and our product, so I can lead our team and help everyone in the company fulfill our mission of helping our members never overpay for travel again.

What's your favorite thing about your role here at Going?

It sounds sappy, but it's the people I work with. My team is so incredibly passionate about getting members great deals and sharing their own passion for travel, and everyone genuinely enjoys working together. We interact constantly and somehow never get sick of each other.

I also am absolutely addicted to member testimonials. When I or someone on my team sends a sweet deal like $316 roundtrip to Tokyo or $370 roundtrip to Italy, and the testimonials from our members start pouring in, I get chills. I get incredibly excited when we can help folks living near smaller airports access parts of the world they never thought possible.

What advice would you give to a candidate interested in working at Going?

Start building your skills, both in your area of focus and in the greater travel sphere. Candidates who come to the table with exceptional talent, a wide variety of experiences (both personal and professional), and a passion for and understanding of travel thrive here. Also, when you're ready to apply, be yourself. One of our core values is 'Be Human,' and we live by it. We're a company composed not only of exceptional talents but of exceptional humans.

What's kept you here for 4 years?

There are three main things. First, the mission. I love helping folks get to travel, no matter the destination. Knowing I've been a part of thousands of people's travel stories gives me the warm and fuzzies. Second, the people. My coworkers here are incredible and deserve the best, and if I can help them enjoy their days a little more or thrive a little more in their work, I'm happy. And finally, it's the lifestyle. I love working for a company that is remote-only. I love the trust the company's leadership has in us to decide the working style that works best for us and our teams. I love the perks (the three months I took off for my daughter's birth were incredible, and getting a little cash to spend whenever I meet up with a coworker is terrific).

Where is the coolest place you've worked from, and why? 

I've worked for Going, sending flight deals from over half a dozen different countries, from Costa Rica to Greece and beyond. While I have a lot of favorite mobile offices, the coolest has to have been on a floating island made of reeds in the Uros, Lake Titicaca, in Peru. Working off my cell phone's hotspot (service was remarkably consistent there!) on a floating island in a lake, almost 4,000 meters above sea level, was a remarkable experience. And being right there meant that the second I was off work, I was immediately immersed in the place and the culture. It was amazing.

What always makes you laugh, no matter what? 

Dad jokes. I've been a dad for almost three years and was born for this thing. I've been making the world's corniest jokes all my life, and they've failed to land with basically anyone except myself. Then one day, all of that changed. I went from being cringy to being a dopey dad. And I love it. I'm not sure what my daughter thinks of it. She's successfully executed the 'roll your eyes at Papà' move a few times. I expect she'll be a real pro at that by the time she's a teenager.

If you want to join Willis and the rest of the Going team, you can check out our careers page for openings!

Published July 5, 2023

Last updated December 28, 2023

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