How Leaders Lead with David Novak · 2026-10-22 · 73 min · 15,654 words

#314: Kyle Leahy, Chief Commercial Officer, WHOOP – Outhire yourself

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Hello and welcome to another episode of How Leaders Lead with David Novak Today's guest is Kyle Leahy. She is the former CEO of Glossier and now serves as the chief commercial officer at Woop. Kyle has built her career on taking on new challenges and learning from each one. And in this episode, you're gonna learn how to keep growing as a leader and how to make the most out of every opportunity that comes your way. Enjoy this conversation with David and Kyle and stay tuned to the very end of the episode, where we'll debrief some of the key takeaways from this conversation so that you walk away with something practical to apply to your life and to your leadership. Enjoy this conversation and I will see you at the Debrief. You know, you you and I have something in common. We just love food and you you're you're a self described foodie.

What's a meal that you've had recently that you just can't stop thinking about? Oh, well, I love food, David, like you said, and I love experiences and trying new restaurants with my husband Mike and our kids traveling the world. Um, but I also love just being at home. So I'd say last weekend, um, I live in Massachusetts and my parents live nearby and they came over with my husband and my kids and my husband cooked ribs and it was just like a cozy ended up being a Nor'easter here in the New England area. So our dream of having kind of a backyard barbecue moved inside, but it was with people I love, with food I enjoyed, and mostly just being connected with with those that I care the most about. That's fantastic. And you said you love to travel. W what was your last big adventure? uh that really lived up to the hype. You know, we get so excited about these the holidays we're gonna go on.

Yeah, I mean, we've uh always been kind of prolific travelers and trying to explore new places, trying to be curious and to learn and explore the world. Uh earlier this year, be f between my time at Glossier and now at Whoop, uh, we went to Southeast Asia with my kids. I've got a seven year old and a five year old who are like the light of my life and at fun, engaging, exciting ages. And so we went to Vietnam and Thailand and Singapore and Laos and really just like introduced them to the world in a really meaningful and powerful way. And it was incredibly memorable, filled of just an incredible sense of culture and the graciousness of the Southeast Asian environment and community filled with food and adventure. It was something I'll carry in my heart forever, for sure. Yeah, I'm sure you will. I spent a lot of time in in Asia as well, and there's there's No place really like it, you know. And you hit on one of the things that we love there, too. It's a great food. It's really fantastic, you know. Now you've just started a a new chapter as the chief commercial officer at Woo.

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