Dr. Kathleen St. Louis Caliento, President and CEO of Cara Collective, traces her dedication to civic leadership back to her early years as the child of Haitian immigrants. She credits her upbringing with instilling values that continue to guide her work today. “From my very first job delivering newspapers, I learned that showing up for my community mattered,” she says.
Her ability to connect with diverse communities is shaped by her multilingual background—she speaks Haitian, French Creole, and Spanish—and the importance placed on community building in Haitian culture. “My Haitian background emphasizes the importance of community building and relationships,” Dr. Caliento explains.
Dr. Caliento’s focus on education led her to earn a PhD in Secondary Science Education and later an MBA after seeing how business could drive systemic change. “Early on, I recognized the importance of education,” she states. “But my educational journey didn’t stop there… My experiences in the business sector showed me a whole new way to drive systemic and lasting change.”
Her leadership path included serving as Executive Director at Spark Program Chicago, which works with middle school students on career exploration. She describes this role as pivotal: “For me, this role was pivotal to my leadership growth.”
In 2021, Dr. Caliento became President & CEO of Cara Collective, an organization focused on employment and economic opportunity for underserved communities in Chicago—a mission closely aligned with her own values. She recalls being excited by the opportunity: “I was already a big admirer of Cara’s work, so being asked to lead such an organization was nothing short of exhilarating.”
Her tenure has included challenges such as navigating through the COVID-19 pandemic and workforce disruptions known as “The Great Resignation.” During this period, she reviewed employee benefits and PTO policies while investing in staff development efforts to maintain stability within Cara Collective’s programs. Dr. Caliento reflects: “This moment taught me to lead by listening first; understanding what participants, staff, and the community needed to feel safe, supported, and seen.”
Among successes at Cara Collective is the tradition called "Motivations," where participants gather each morning for reflection and connection before beginning their day’s work together—a practice Dr. Caliento highlights enthusiastically: “Each morning, participants gather to reflect on a daily topic, share their stories, and end with a unifying song and dance.”
A notable achievement under her leadership is the opening of Englewood Cleanslate Facility in 2022—part of Cara's social enterprise efforts—which not only provides exterior maintenance services but also hosts programming tailored for local needs onsite. In its most recent year alone nearly 750 transitional jobs were created through Cleanslate.
Dr. Caliento’s commitment extends beyond workplace initiatives into broader civic engagement across sectors like education, workforce development, health care access, and housing support—though she identifies motherhood as her proudest role.
She draws inspiration from Bryan Stevenson’s emphasis on proximity when working toward social change: "Kathleen believes that this is the core of Cara Collective; that being close to the community and facing their issues is important to show up for those who need it."
Cara Collective continues its mission at 237 S. Desplaines Street in Chicago.