A 12-year-old girl pedals through the rain on a Sunday morning. Stacks of newspapers are balancing on her bike, unknowingly building values that would later define her future in civic leadership.
Dr. Kathleen St. Louis Caliento’s journey to becoming President & CEO of Cara Collective starts with her upbringing. Born to hard-working Haitian immigrants, she carries the lasting impact of their sacrifices. “Their journey shaped my values of determination and perseverance,” Kathleen says. “I’ve always felt a deep responsibility to honor their efforts by striving to be my best, to ensure their sacrifices were never in vain.” From her very first job delivering newspapers, she learned that showing up for her community mattered. “My customers counted on me to deliver their papers on time, and I learned that reliability and consistency weren’t optional — they were the job.”
Her multilingual background, fluent in Haitian Creole, French, and Spanish, is also a big component in her ability to connect with communities. “I’m a firm believer in the power of language and culture to build genuine connections,” she states. “It’s one of the most meaningful ways to bridge differences and foster trust”. Her Haitian background emphasizes the importance of community building and relationships, which has heavily influenced her leadership style. “In Haitian culture, community is everything,” Kathleen explains. “We lift each other up, we care for our families, and we don’t succeed alone. That spirit has stayed with me, and it’s central to how I lead.”
Early on, Kathleen recognized the importance of education. This realization led her to a PhD in Secondary Science Education. “I wanted to learn everything I could to drive meaningful change and expand access and opportunity for all,” Kathleen states. But her educational journey didn’t stop there. Her experiences in the business sector showed her a whole new way to drive systemic and lasting change. “That experience showed me the potential of combining mission-driven work with strong business principles to create lasting impact,” Kathleen explains. “It also motivated me to learn the language of the business world so I could bring those tools and strategies into the social impact space.” So, with this, Kathleen also pursued an MBA.
While her academic journey gave her the tools for systemic change, it was her entry into executive leadership that would shape her next chapter. Her first Executive Director role was with Spark Program Chicago, a Career Exploration program that works with Chicago’s middle school students. For Kathleen, this role was pivotal to her leadership growth. “It challenged me to step fully into accountability and helped me understand the true power of partnerships in driving social impact,” says Kathleen. “It was a turning point in how I thought about scale and sustainability: meaningful partnerships weren’t just helpful — they were essential to growing our impact.”
In 2021, Kathleen assumed the role of President & CEO of Cara Collective; an organization whose values aligned closely with her own. She was already a big admirer of Cara’s work, so being asked to lead such an organization was nothing short of exhilarating. “I remember when I first got the call—I thought, ‘Did you get the right number?’” Kathleen recalls. “Knowing I would have the chance to shape the strategies that will guide us for the next 30 years filled me with a mix of shock, excitement, and joy.”
Her time with Cara, much like any large role in such an important organization, has had its setbacks and successes. One significant setback Kathleen experienced (within her first year at Cara Collective, no less) was the COVID-19 pandemic. The pandemic was hard on a lot of communities and organizations. In 2021, over 75% of nonprofits reported job vacancies greater than 10%, and Cara was no different. “At one point we peaked with about 36% staff attrition in late 2022,” she states. “The Great Resignation” pushed her leadership skills to the test. “You think you can rely on a crisis manual for moments like that, but the reality was unlike anything we could’ve prepared for,” Kathleen explains. She responded by reevaluating employee benefits and PTO policy, ensuring competitive compensation, and investing in staff development. Kathleen reflects that this moment taught her to lead by listening first; understanding what participants, staff, and the community needed to feel safe, supported, and seen.
Despite the hardest days at Cara Collective, Kathleen speaks most passionately about the victories. “At Cara Collective, we believe in celebrating every milestone,” she states. “From the moment a participant rings the bell to mark their new job, to seeing them return a year later to proudly graduate from our program, each moment is a powerful reminder of what’s possible.” She lights up when talking about “Motivations”, a Cara Collective tradition she describes as “better than any cup of coffee that you could have in the morning.” Each morning, participants gather to reflect on a daily topic, share their stories, and end with a unifying song and dance. “It’s just really beautiful to hear how people come together once that vulnerability is revealed,” Kathleen says.
One standout memory was the grand opening of the Englewood Cleanslate Facility in 2022. Cleanslate is a Cara social enterprise, helping transform communities and neighborhoods through exterior maintenance like litter abatements, snow and graffiti removal and even light landscaping. This past year alone, this program provided nearly 750 transitional jobs. But the Englewood opening was unique. While most facilities focused solely on operations, this one began hosting programming on-site in response to community needs. Kathleen recalls that “We had not intended [doing programming at Englewood] at all,” yet there was such a large need for additional economic support in the community, “we had to pivot because we wanted to listen to the community members. Now, for the first time in any Cleanslate facility, we started providing programming.” Kathleen reflects:
“What made it even more meaningful was being welcomed into a neighborhood that has historically faced deep disinvestment. From day one, we began to see the impact of our presence — more job seekers walking through our doors, and powerful partnerships forming to support them. It was a clear sign that we were exactly where we needed to be, doing the work that matters most.”
Kathleen has a deep commitment to civic leadership, extending far beyond just the workplace. “It’s simply part of who I am,” she states. While she celebrates her multifaceted impact across several sectors—education, workforce development, health, and housing—her proudest role is being a mother. “Raising my daughter Mia is one of my greatest joys,” she claims. “She’s an incredible, spunky, empathetic, kind, and curious young person, and it’s a true privilege to watch her grow into who she’s becoming.”
From simply biking her paper route to leading a movement for opportunity, her path has always been about showing up. Kathleen shares a quote from Bryan Stevenson’s Just Mercy that she resonates with, “Proximity has taught me some basic and humbling truths, including this vital lesson: Each of us is more than the worst thing we’ve ever done.” 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. She explains, “We strive to bring our partners and supporters directly into the work, so they can experience it firsthand, form genuine connections, and truly understand the critical role we all play in addressing poverty.”
Learn more about CARA Collective Chicago & Dr. Caliento’s Amazing Work:
🌐Website: caracollective.org
📱Instagram: @carachicago
📍Location: 237 S. Desplaines Street
🎟️Get your tickets for Cara’s Summer Social on Thursday, September 4, 2025 from 6pm-9pm!
