Bold, Not Bossy: Ivybrook Academy COO Amy Cowan on What It Takes to Lead in Early Childhood Education

Twenty-six years ago, Amy Cowan stood at the front of a third-grade classroom. Today, she helps lead a preschool franchise with more than 60 campuses open and another 75-plus agreements signed. What happened between then and now is not a straight line. It never is.

In a recent episode of Childcare Conversations with Kate and Carrie, Ivybrook Academy’s Chief Operating Officer sat down to talk about her path from public school teacher to franchise executive, and about what it actually means to lead boldly in a field that has historically underestimated its own leaders. The conversation ran 25 minutes. It could have gone longer.

She Built Up to This From Inside Schools

Before Ivybrook, before franchise operations, Amy was in the trenches of public education. Third grade. Then interventionist work. Then instructional coaching and school administration. Those details matter because they shaped what kind of leader she became. She did not arrive at a COO role through a business school program or a corporate ladder. She arrived through schools, through teachers who needed support, through parents who needed to trust someone.

When she relocated and eventually joined Ivybrook Academy, she came on as an assistant principal at the Weddington Campus. That is worth noting. She learned the model from inside a school building before she ever learned it from a corporate office.

The Mentor Who Left a Mark

Ask Amy about her leadership philosophy and she goes back to one person: a female principal she worked under early in her career.

This was someone who did not gatekeep. Who actively pulled other women up. Who led with confidence without making confidence feel like a performance. “She modeled bold leadership,” Amy said.

Bold leadership, in Amy’s telling, is not about volume or dominance. It is about showing others what is possible and then making space for them to get there. That mentor did not just inspire Amy. She gave her a template for what to do when she eventually had the position to do it herself.

This is the kind of influence that compounds over decades. And it is visible in how Amy now approaches her own role at Ivybrook.

Saying Yes When It Feels Too Soon

One of the clearest threads in Amy’s conversation is her relationship with discomfort. She has learned to treat it as a signal, not a stop sign.

Her guidance for women who want to grow into leadership is direct: when an opportunity makes you a little uncomfortable, that is your cue. Not to hesitate. To say yes.

This is not recklessness. Amy is specific about the preparation that needs to happen first: researching the people you are meeting, walking in knowing what you want to communicate, being ready to listen as much as you speak. But the preparation is in service of showing up, not of finding a reason to step back.

She is also honest about something most leadership advice glosses over: confidence often comes after you start, not before. You do not wait until you feel ready. You show up, do the work, and let competence and confidence build each other along the way.

What “Bold, Not Bossy” Actually Means

Amy’s phrase for her leadership style is the kind of thing worth writing down.

Bold, not bossy.

What she means: you can be clear, direct, and confident without running people over. You can hold a room without shutting others out of it. Assertiveness and respect are not at odds with each other. In Amy’s approach to leadership, they are inseparable.

This is also the culture she works to reinforce across Ivybrook’s growing network. The same attention to how people feel in a space, the same belief that every person in the room brings something worth hearing, the same conviction that how you treat people is not separate from the work. It is the work.

What Families Should Know

When you tour an Ivybrook campus, you are walking into a place where the leadership structure runs deep. Amy Cowan brings 26 years of early childhood education to every operational decision: how campuses are supported, how school owners are trained, what consistency looks like across locations.

The philosophy that guides Ivybrook classrooms, the Reggio Emilia and Montessori approaches, the focus on each individual child, does not happen by accident. It requires people in operational roles who believe in it and know how to build systems around it. Amy is one of those people.

What Franchise Prospects Should Know

If you are exploring Ivybrook Academy as a business opportunity, Amy Cowan’s background is part of what you are buying into.

The support she provides is not generic. It is built on two and a half decades of knowing how schools actually run, what teachers actually need, and what families are actually looking for when they walk through the door. That context changes the quality of the guidance.

She talks about skill sets as something always being built, never finished. That same belief runs through how Ivybrook supports its school owners. Training is a starting point, not an endpoint.

Listen for Yourself

The full episode is worth 25 minutes of your time. Amy is specific, direct, and warm in equal measure. She does not speak in abstractions about leadership. She speaks from experience.

You can find Childcare Conversations with Kate and Carrie, Episode 365, wherever you listen to podcasts, or watch it on YouTube here.

Amy Cowan serves as Chief Operating Officer of Ivybrook Academy, a national half-day preschool franchise built around a blended Reggio Emilia and Montessori approach. Learn more at ivybrookacademy.com.