Courtenaye Jackson: - From Prosecutor to Purpose: A Journey to Justice

What does it mean to lead with purpose, principle, and power?

This episode features Courtenaye Jackson—currently General Counsel for the Children’s Aid Society in New York City. With a $300M endowment and a wide portfolio of schools and social services, Courtenaye brings legal expertise and deep conviction to systems in service of children and justice.

But her path wasn’t linear. From growing up in Queens with dreams of being a forest ranger, to tipping sheep at Cornell, to launching a powerful legal career that has spanned the Manhattan DA’s Office, human trafficking interventions, and a decade as General Counsel for the NYC Department of Education, Courtenaye has lived what it means to fail forward.

Together, we explore:

• How formative failures taught her what her real “genius” is
• The ethical weight of criminal prosecution—and why she left it
• Stories of trauma, resilience, and redemption in the justice system
• How to lead when your team might not all be aligned
• What it means to truly change a system, not just work in one
• How compassion and justice go hand in hand

Courtenaye’s work invites us to ask:
Are we building systems that solve problems—or perpetuate them for profit? 

Are we willing to reset when the path we chose no longer serves our purpose?

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Learn More:

•Children’s Aid Society

•NYC Department of Education

•Center for Justice Innovation (formerly Center for Court Innovation)

•Midtown Community Court

“I think we’re all called. Not everybody gets to pick what they’re good at. I think that’s part of the design—your genius is the packaging for your purpose.”

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Producer, editor and host: Ryan Maxwell

Theme music: Ryan Raddatz

Guitar music: Adeline’s Guitar

The views shared on this podcast are those of my guests and the host and do not necessarily reflect those of any employer past or present.