Kathleen St. Louis Caliento’s journey into leadership is rooted in her personal experiences as the daughter of Haitian immigrants who faced systemic barriers in achieving professional recognition and opportunity. Inspired by her parents’ resilience and focus on possibility, she has spent nearly three decades addressing issues of social justice, particularly in the areas of educational equity, workforce development and economic empowerment.
Caliento is a visionary leader in the nonprofit sector, serving as president and chief executive officer of Cara Collective, a Chicago-based workforce development organization founded in 1991. Cara Collective’s mission is to build an inclusive economy by creating employment pathways that empower individuals and uplift communities. Under her stewardship, the organization has continued its 30-year legacy of placing individuals affected by poverty into over 15,000 jobs, advancing economic self-sufficiency through its four entities: Cara, Cleanslate, Cara Connects and Cara Plus.
A key highlight of her tenure at Cara Collective has been the relocation of Cleanslate operations to Englewood, which resulted in a 60% increase in program interest and a 30% rise in participant engagement. Cleanslate now serves over 500 transitional workers annually, providing valuable work experience and paving the way to long-term employment. Additionally, Cara Collective launched the Cara Accelerator Program, a fast-track initiative that reduces time to job placement for participants ready to move swiftly into employment.
“Every time I hear a participant’s story of transformation – whether it’s landing a job, signing their first lease or achieving an educational milestone – I’m reminded why we do what we do,” said Caliento. “These stories fuel my passion and commitment.”
Recognizing the transformative power of technology, Caliento has integrated digital literacy into the organization’s core programming, equipping participants with the skills needed to thrive in an increasingly digital economy. These innovations have yielded measurable success, with 976 jobs secured in FY24 and $7.3 million in annual participant earnings.
Caliento’s accomplishments extend beyond her role at Cara Collective. She is a published author and holds a Ph.D. in secondary science education from Columbia University. Her leadership has been recognized nationally, with speaking engagements at conferences like ASU+GSV and op-eds featured in Crain’s Chicago Business. In 2023, Cara Collective received an $8 million unrestricted gift from philanthropist MacKenzie Scott.
“Dr. Caliento’s leadership style is both empathetic and strategic – she understands the complex barriers that individuals face and works tirelessly to create an inclusive environment where everyone has the opportunity to succeed,” said her staff. “Her approach is holistic, addressing not just the immediate needs of employment but also the underlying issues that can hinder long-term success.”
