The Fine Line | CAROLINE GILROY

Caroline Gilroy is a co-founder, mother, and creative.

As a mother of four, Caroline navigates the beautiful, messy intersection of ambition and family life. That lived experience carries into her work as a creative entrepreneur building a brand from the ground up — placing her squarely within The Fine Line, where leadership, creativity, and caregiving constantly overlap, and balance is defined less by perfection and more by presence. Alongside Agee Gretta Leinberry, she co-founded Couper, a multi-brand online destination featuring exclusive, museum-worthy capsules in women’s ready-to-wear and accessories.

In this conversation, Caroline reflects on what it looks like to lead a growing company while staying deeply connected to her family. She shares how she releases guilt, invites her children into the reality of her work, and models resilience, teamwork, and heart along the way. Her perspective is a reminder that success is rarely linear, or solo, and that building something meaningful can coexist with raising thoughtful, grounded humans.

How do you stay connected with your family while managing a busy career leading Couper?

I’m very intentional about the small things. Mornings, school drop-off, bedtime… those are sacred to me. I also try to blend worlds when I can: kids popping into meetings, trips that mix work and family, letting them see what I’m building in real time. It’s not about perfect balance (that doesn’t exist), but about presence where you are.

What advice do you have for working moms?

Release the guilt. It’s not helping anyone. There will be seasons where work needs more of you and seasons where your family does, and both are okay.

Build a support system you trust, ask for help without apology, and remember that showing your children what passion and commitment look like is a gift, not a trade-off.

How do you involve your children in understanding your work, and what do you hope they learn from watching your career?

They’re very aware of Couper. They see the clothes, the piles of boxes, the photos, the chaos and the wins, but they also see the hard days. I don’t hide the losses or the moments when something doesn’t work out the way we hoped. I talk to them about rejection, about trying again, and about the fact that building something meaningful is never a straight line.

They also see how much I lean on my husband and how we support each other, divide and conquer, and show up as a team. I want them to understand that success is rarely solo, and that asking for help is a strength, not a weakness.

More than anything, I try to show them resilience, humility, and heart.

That it’s okay to dream big, to fail loudly, to work hard, and to do it all with kindness and gratitude along the way - especially towards the people who are working with you along the way.

FOLLOW ALONG

Follow Caroline’s journey on her Instagram, and shop Couper here.

Follow Brigade Events and stay tuned for the next iteration of The Fine Line at @brigadeevents.

We’d be honored to include you — or a woman you admire — in this series. If you or someone you know has a story to share, we’d love to hear from you. Reach out to us at carly@ingoodcompanypr.com. Together, we can uplift, support, and redefine leadership for the next generation.

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