Leading on the Court and in Business: Rachel Wagenman

Serving Up Stories and Strategy: How Pickleball Inspires This Honolulu Marketing Leader

Meet Rachel Wagenman, Director of Marketing and Communications at La Pietra Hawaii School for Girls. A proud La Pietra alum, she returned to her alma mater to share the stories that shape its community and to create opportunities that empower the next generation of young women.

When she’s not leading marketing efforts at La Pietra, Rachel is giving back—whether through volunteer work, creating content for Outrigger Canoe Club’s publication, or battling it out on the pickleball court.

Rachel sees the parallels between leadership and pickleball—and she sat down with us to share her take on both.

Currently residing in:

Honolulu, Hawaii

Where did you grow up and what high school did you go to?

I was born and raised on Oahu. Grew up in Kalihi and Aiea, but went to school at La Pietra – Hawaii School for Girls near Lēʻahi. I’ve always been driven, but I really think that La Pietra taught me to embrace who I am as a person, be a strong yet compassionate leader in my community, and to follow my passions.

How did you discover pickleball, and when did you start playing?

My husband Aaron and I are often in the Kakaako area, so when the new courts opened in 2021 at Mother Waldron Neighborhood Park, we were intrigued! We bought two paddles and some balls from Target just to try it out, but we quickly started playing often for fun. I played tennis in high school, so it was a fun, low-pressure way to get back into racket sports.

What do you love most about pickleball?

I’m a competitive person, so I love the thrill of being up at the kitchen in the middle of an intense rally—just battling it out!

But what makes pickleball really fun is how easy it is to pick up and play, making it a sport that brings people together.

One of my favorite things is playing with Adrienne Kadokawa (pictured above), one of my best friends since high school. We played basketball together back then, and now our doubles matches with our husbands bring back that same competitive fire—just on a different kind of court!

How often do you play?

Not often enough! With courts in such high demand, my husband and I try to set up our own net at parks around town to get in some play time when we can.

What paddle are you using, and what do you like about it?

I play for fun, so when it comes to the paddle I use, it really comes down to the aesthetics. One year for Christmas, I bought my husband a super cute paddle from Recess online, and I got myself one to match. Does anyone else do their holiday shopping like that—one for you, one for me?

Outside of work, my husband and I love to travel—especially cruising. We recently got married on a Disney cruise to Alaska, which was an unforgettable experience!

Next on our list is a Mediterranean cruise, and eventually, we’d love to do an Antarctica expedition cruise.

When I have some time to myself, I love hiking Makapu‘u and supporting local businesses—whether it’s trying new restaurants or hanging out at cute coffee shops with friends. Fun fact: I used to be a big Yelper! I still enjoy writing the occasional review when I find a great spot worth sharing.

What do you do outside of pickleball?

Outside of pickleball, I’m the Director of Marketing & Communications at my alma mater, La Pietra – Hawaii School for Girls.

I love sharing the incredible stories of our community—whether it's the outstanding achievements of our current students or the remarkable paths our alumnae are forging in their careers. I’m always cheering for the sisterhood!

I consider myself a storyteller, so it’s no surprise that outside of my day job, I’m the editor of Outrigger Canoe Club’s Ama Magazine. I’m also a member of the Chamber of Commerce’s Young Professionals and the Organization of Women Leaders. I’m also actively doing volunteer work with the American Lung Association in Hawaii as the chair of the Young Leaders Cabinet and as a member of its Women’s Cabinet.

You’re the Director of Marketing & Communications for La Pietra – Hawaii School for Girls. Pickleball is sometimes compared to business—strategy, adaptability, and teamwork all play a role. Do you see any parallels between the game and your work?

Yes, definitely! Just like in pickleball, in my role at La Pietra, I'm constantly thinking a few steps ahead. Whether it’s crafting messaging that resonates, anticipating trends, or adjusting strategies in real time, success relies on strategy, adaptability, and teamwork. On the court, you read your opponent, make quick decisions, and adjust your game plan—similar to marketing, where understanding your audience and staying flexible is key.

Pickleball also teaches the value of collaboration, much like how marketing at La Pietra involves working closely with various departments, alumnae, and community partners. Just as a team on the court must communicate and support each other to succeed, we work together to advance the school’s mission, ensuring that everyone is aligned and moving forward with a shared goal.

And, of course, both require some finesse—placing the perfect shot or delivering the right message at the right time.

If you could invite anyone—business leaders, mentors, or colleagues—to play a game of pickleball with you, who would it be and why?

My boss, La Pietra’s Head of School, Jen Grems! She is a paddle tennis player through and through, so it was a big deal when she first picked up a pickleball paddle. I won’t say she’s converted yet, but I’d love to challenge her to a match!

What’s one lesson from pickleball that you think every professional should apply in their work?

The power of having fun. Pickleball is an exciting, fast-paced game that's lighthearted even when things get intense.

In the professional world, having fun and not taking yourself too seriously can lead to better teamwork, more creativity, and a positive work environment. Sometimes taking a step back to have fun, spitball ideas, and let off steam gives you the creative freedom you need to come up with your best solutions.

When you create space for fun, it fosters creativity and builds stronger connections, which ultimately leads to greater success.