Get Closer

Get Closer: Kathleen St. Louis Caliento of Cara Collective

October 11, 2023

There is a growing recognition that the education-to-employment systems in America are not working for most people. That’s why New Profit is investing in visionary social entrepreneurs who are creating access to postsecondary and career opportunities for young people from historically overlooked communities and driving economic mobility.

Each leader is advancing a different approach, with a model that is deeply responsive to the needs of the communities they work with. What these leaders have in common is that their insights, expertise, and efficacy come from their first-hand experience with the systems they aim to shift, and their close connections to the communities they aim to serve.

In this series of dialogues, we get closer to these proximate leaders and their organizations to highlight the ideas, insights, and innovations that are advancing equity and opportunity in America.

Kathleen St. Louis Caliento is the President & CEO of Cara Collective, an organization dedicated to helping people experiencing poverty develop the skills and confidence they need to get and keep gainful employment. Kathleen has over two decades of experience in urban education, student success, and dismantling social injustices.

Abby Marquand is a Managing Partner on the Economic Mobility team at New Profit, leading the venture philanthropy organization’s efforts to support proximate leaders building new systems of opportunity in the United States.


Abby: I’m so excited to finally be having a chance for a deep dive with you, Kathleen. Can you start by telling us a bit about your story, and how you got into this work?  

Kathleen: I am the daughter of Haitian immigrants, and there were many times that my parents faced inequity and were denied access and opportunity. In particular, I think a lot about the resources that our family needed not just to survive, but to thrive educationally and professionally. I think about the systemic hurdles my parents were trying to overcome, navigating the educational system and all the unknowns of the professional world. My father used to say something very harsh to me, which was: “you are Black, and you are a woman, and that’s two strikes against you. No one’s going to listen to anything you say unless you have an education.” So education was always very, very highly valued in our family. Watching what my parents went through definitely drives the work that I do, it’s the reason I started my career from an educational reform perspective. 

Abby: How does that drive your point of view leading Cara Collective? 

Kathleen: From working in education reform, my career has slowly started to shift, because so many of these social determinants are intertwined. The fact that I’m now squarely in workforce development is actually not very far removed from the work that I was trying to do in education reform, such as fighting for equity, high-quality teachers in schools, and ensuring that everyone had access to information to make decisions for their children’s education. So even in my educational work, I tried to create pathways for students’ futures, working with them in school to place them in internships and to help them understand and recognize what is possible for their careers, and to help companies recognize that upcoming talent in them. Unfortunately, in this society, we have systems in place that are meant to keep certain people from accessing certain resources, and that has really been the impetus of my work: making sure that folks have the access they need to make the best decisions they can for themselves and their families.

Abby: A number of things you’ve said really struck me, but in particular, I want to go back to the way you spoke about “the unknowns” that exist within the professional world. People have to navigate the hidden systems and networks that exist, so many that were designed with purposeful inequity towards specific demographics. In the field, we hear a lot about the importance of “social capital” in navigating these systems and structures. How do you think about social capital at Cara Collective?

Kathleen: It is absolutely integral to our vision. We fuel a national movement to eradicate financial and relational poverty. People typically understand what we mean when we say eradicating financial poverty, but we often get asked what relational poverty is, and that’s exactly the social capital you’re asking about. The folks we serve have experienced missteps, misfortunes, or injustices, and are often told they need to be defined by those experiences. We spend a lot of time rewiring that thinking, proving on a day-to-day basis that there is a community that cares about you, even when you make a mistake, even when you face injustice. So, social capital is really inherent in our model. We also talk about the importance of networking, to set participants up with further resources and support through their next steps. Folks graduate from Cara not when they secure a job, but when they’ve been at that job for a year, because we understand that landing a job won’t make all a person’s problems magically disappear. We assign them retention coaches who can continue to support them and help them navigate the trajectory of their career and their workplace relationships. 

Abby: It’s clear that you, as a leader, believe that these problems are multi-faceted, and in order to actually create an inclusive economy, we need to tackle multiple issues. One thing that’s so compelling about Cara Collective is that you entwine the workforce development piece with other programs. Can you talk about those a bit?

Kathleen: About two years ago, we rebranded to Cara Collective, which houses four entities: Cara, Cleanslate, Cara Connects, and Cara Plus. The first entity is Cara, our traditional program for professional and personal development. That’s where folks come in, learn about each other and themselves, and get the skills they need to be successful both in jobs and as humans. We recognize the trauma and other factors that might be holding some of our folks back, and we set up support programs to help them work through these. So we include networks to assist in areas like housing, childcare, and legal aid. We’re also building up our mental health support resources for our participants. 

Then, we have our two social enterprises; Cleanslate and Cara Connects. Cleanslate, our flagship, is a neighborhood beautification company we launched because we recognized that folks who were either returning citizens or had long gaps in employment on their resumes were having a more difficult time landing jobs. Cleanslate is a way for us to provide this population with transitional employment, allowing them to build their resumes, hold down a job, hone some competencies and skills, and eventually use that as a launchpad for a permanent role with one of our employment partners. The other, Cara Connects, is our staffing firm that partners with leading employers across the city to place folks in temporary or permanent positions.

Finally, we have Cara Plus, which was raised as an entity to help us multiply our impact, share best practices, and work as a thought leader in the field. We work with other workforce development organizations and employers across the country to develop their inclusive employment practices. As we’re geographically expanding into new cities, these collaborations are important ways to get to know other social service committees, their constituencies and the people they serve.

Abby: I love how the four entities you mentioned all build on one another, and it’s so powerful how you’ve been able to leverage those to create real influence on employers. You also mentioned that Cara Collective is intentional about connecting with the organizations that already exist in the communities you enter. Something we talk a lot about here at New Profit is proximity, and it sounds like it’s also something that your model prioritizes. What does proximity mean to you and how does it show up in your work?

Kathleen: Bryan Stevenson, whose work I find really inspiring, often says the folks whose problems are being solved are not at the table creating the solutions. That’s why proximity is so important, because although we implement strategies, resources, and opportunities, we can’t purport to know what’s best for people. It’s very important to me that dignity is prioritized, and that we aren’t connecting folks with job opportunities in a way that implies they owe us gratitude, but in a way that works for them and aligns with their career goals. Is this what they want to do? Will it lead them down the path they want to go? Will it make them happy? 

But you can’t do that without proximity. So for us, formalizing evaluation and feedback from our participants helps us tailor our interactions and programs. I also think it’s so important for us as leaders to get an understanding of our folks and where they’re coming from by spending time together in person. The same goes for employers. Last year, we brought in 25 top executives from Allstate, a big investor in our work, and we essentially put them in the ring with our participants. They came out saying that out of all their years doing this, it was the most moving, productive, and real experience they’ve had, just because they were able to talk honestly. It was incredible because it’s more than meeting a recruitment quota, it’s about understanding programs like Cara—that enable you to get closer to people—are the ones that make the difference. Proximity is critical.

Abby: It sounds like you really value an asset-based approach where people bring their own motivations, strengths, and narratives, and you’re prioritizing those, which is not always how traditional workforce development programs work—historically just assigning bodies to open positions. What’s one thing you wish people knew about Cara?

Kathleen: Our job seekers want to work. So many frontline workers and workers that have been impacted by the criminal justice system are motivated and they are applying to advancement opportunities, internally and externally. The narrative that they’re lazy or taking advantage of benefits is tired. These workers are actually prioritizing their career advancements and it’s employers who aren’t responding to those needs. It’s also important to understand that folks who experience injustices are primed to make missteps, but given the opportunity, they will rise to the challenge every time. They are often willing to work harder than those who have had easier routes to securing work. 

Abby: Dismantling those narratives is powerful. How does Cara see itself in the ecosystem? How do people look to you in the thought leadership space?

Kathleen: We never want to come across like we know everything, we want to contribute to an ecosystem that creates a more inclusive economy. So we’re intentional about how we occupy spaces and how we consider differences. Cara considers education in different ways—It’s all intertwined, but through innovations like our retention coaches, we’re able to set ourselves apart and have a valuable voice in the space. We also emphasize that for employers, workforce development is not a numbers game. They’re missing something fundamental: the people.

We’re entering year two of our strategic plan, which we’re excited about because those four priorities are just so crucial. Going back to the proximity piece, it’s truly about deepening participant experience. I also want to emphasize how important it is for us to think about our role in communities. We just bought a new building for Cleanslate in the Englewood community. Now, we’re partnering with the local community organizations who have been fighting there for so much longer than we have. We are able to refer our folks to some of their programs, and vice versa, which is wonderful.

Abby: In the field, where are you finding inspiration right now?

Kathleen: Particularly in terms of corporations, I’m inspired by the folks who are putting their money where their mouth is. Here in Chicago, there are a few I can think of who have created pipeline programs to ensure that there are pathways to economic fulfillment for our participants. I’m also inspired by our participants. We provide the social network and capital, but they change their own lives. In light of all the obstacles they’ve faced, we see people from all stages of their lives who decide to break cycles and make a difference for themselves and their families. And that’s what drives me every day.