Kathleen Caliento

President & CEO, Cara Collective

Dr. Kathleen St. Louis Caliento has spent the past two decades committed to urban education, student success, and dismantling social injustice.

As the President & CEO of Cara Collective, she leads a social purpose enterprise with 30+ years of experience helping people affected by poverty (and often the interrelated challenges of recovery, domestic violence, episodic homelessness, incarceration, and systemic inequity) to get and keep quality employment. Further, Cara Collective works with employers and organizations across the nation to create more equitable workforce solutions and build a more inclusive economy for all. Through its four entities, Cara Collective produces more than 1,000 jobs each year, at retention rates more than 20 points higher than national norms.

Before joining Cara Collective in 2021, Caliento was the Chief Learning and Design Officer of the Academy Group where she led program design, data utilization strategy, professional development, DEI, and career and leadership development. As part of the founding team, she worked to dissect systemic issues that limit youth’s sense of possibility and pushed for experiences that boast rigor, radical equity, and a robust belief that the talent coming up behind us deserves the access and opportunity to learn and lead in world-changing ways.

Previously, Caliento held several leadership positions at Spark, including Executive Director of Spark Chicago. Prior to Spark, she was Chief Program Officer for Project Exploration, Director of Program Investments for The Chicago Public Education Fund, and a teacher in New York City Public Schools.

Caliento served on the University of Chicago Consortium on School Research Steering Committee for almost a decade and is a graduate of the University of Chicago’s Civic Leadership Academy. A Leadership Greater Chicago fellow since 2020, Dr. Caliento is a trustee of Adler University, serves on the Leadership Greater Chicago LFA board, is a founding board member of EPIC Academy, and a member of the Economic Club of Chicago.

A published author, she earned her doctorate and master’s degrees from Teachers College, Columbia University and graduated with a bachelor’s from Stony Brook University. Originally from New York City, but calling Chicago home since 2003, Caliento enjoys running, playing the guitar, and traveling with her family.