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Chimers in Leadership: Meet Lindsay Chastain, VP of Growth Marketing

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“You only know what you see, and I grew up seeing most women on a path that I wasn’t excited about,” says Lindsay Chastain (she/her/hers). “Then there was my neighbor - she wasn’t on the same schedule the other moms were, and I was so curious about what she was doing as a corporate executive. It was the start of my ongoing journey to find a path that fits for me rather than taking the one already laid out. That neighbor is still a mentor to me today.”

Here’s a look at Lindsay’s path to leadership and how she brings her authentic self to her role as a leader every day.

A natural leader.

“Leading has always come naturally to me—I’m an independent firstborn kid,” Lindsay says. “I’m typically quick to jump in and push things forward.”

Lindsay was thrown into her first formal leadership position in her role as the first digital marketing lead launching e-commerce at a legacy retail brand: “I had to lead a project that nobody else really understood, bringing together agencies and contractors and educating the company about ‘this thing called digital,’” she says. 

“In much of my career, the scope of my team or the projects I’ve led have expanded because no one else wanted to drive. I get a lot of energy from solving problems and creating environments where people thrive—and doing so in new, innovative spaces is always an added, exciting challenge.”

Pushing boundaries and finding her own way.

Although leading comes naturally to Lindsay, her journey to leadership hasn’t been without its challenges—or lack of representation for her to look up to. “It has been a challenge to figure out how to bring my authentic self to my role as a leader, especially when there aren’t always models to follow,” she says. 

In the women she has seen represented in leadership, Lindsay has found encouragement to lead in a way that’s uniquely and authentically her own. “I’m the type to push up against things and see what sticks—all of which helps me understand boundaries and where I can thrive,” she says. “I’m able to recognize that I won’t be successful everywhere, and I’m totally ok with that.”

While Lindsay is very familiar with existing ideals around being a leader—she’s been working on a new approach that better fits her. “I’m on a new journey where I don’t care if I get the credit, and letting go of the ego that comes with that has been an exciting development,” she says. “It’s made me realize you don’t always have to lead from the front, in fact, you can lead without people even knowing you’re leading. Because when we look at what it means to be a successful leader, it means achieving things as a whole team—not as an individual or a function—so debating who gets credit shouldn’t matter if we’re achieving the desired outcome.”

What’s more, many women are naturally less inclined to lead from the front—Lindsay included. “It’s taken me a while to figure out how to show up authentically while still making my voice heard,” she says. “I’m by no means shy, but I also don’t need to hear my own voice in every meeting. It’s been fun exploring how to be authentic in the room and figuring out what works for me. The first step was letting go of any need to be like anyone else and then embracing my own style.”


Finding her own version of success and building trust with her team.

As a leader, Lindsay stays focused on inspiring her team, creating an environment where they can thrive, and then getting out of their way. When it comes to measuring her success as a leader, she looks to her team: “Are the people around me thriving? Are we achieving our vision? Is everyone staying curious and engaged?” she says. “And what that really rolls up to is: Are we having fun? If it’s not fun the majority of the time, then we need to do something differently.”

One lesson she’s learned navigating her own path as a leader is that impostor syndrome is real: “I’m constantly making decisions without complete information,” she says. “Whether right or wrong, it’s more about continuously learning, recognizing your mistakes and correcting them. A big part of feeling safe doing so is building trust: “Building trust is critical; you have to trust the people you work with and they have to trust you,” she says.

“I like to push boundaries and take things apart—I’m in a constant state of reflection and revision, including on the state of leadership,” she says. “I strive to advance societally-driven acceptance of all types of leadership and believe that anyone can be a leader, no matter their role.”

She’s done just that and pushed boundaries at Chime, launching a pilot program for the development of young women leaders at Chime. “It’s about being your full self as a leader and helping people thrive in any environment, as well as how to navigate the many things women can struggle with, such as finding your voice and claiming your space,” she says.