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When Tom Owens started connecting homeless adults with job opportunities, he did it out of the back of his car. Twenty-eight years later, this one-man initiative – which became Cara Chicago – has evolved into a program that includes socio-emotional training, job placement, and one-year retention coaching, that has helped adults experiencing poverty get 10,000 jobs at 70% one-year, same-firm retention rates. And now it’s being done in three cities across the country.

Cara wasn’t developed with national scale in mind, but it evolved based on the observed needs of our participants. At Cara, everything we do is intentional – the way we motivate participants by nudging them out of their comfort zones to do more than they ever thought possible; the affirmation participants receive by “ringing the bell” when they get a permanent job or getting their plaque on the Great Wall when they make it one-year at the same firm; and the community we create to provide the support system our participants often lack. We knew that our success wasn’t in specific activities we could just write down and distribute; they were based on guiding principles that would take the right culture to succeed. We kept this top of mind as we started to explore scaling models through the support of Stand Together Foundation.

With Stand Together’s investment, we established our Expansion department to bring our vision to life. We leveraged Stand Together’s research capabilities to assess potential markets on key metrics like poverty, crime, unemployment and education. This data alone was not enough to determine where Cara should expand – we knew that trust within the community was key to our success. Not only would we need the trust of prospective participants, but also of local employers. Our model would only succeed in a new city if we worked with organizations already embedded in the local ecosystem and steeped in the culture of the people that lived there. We saw this work when Lutheran Social Services of Indiana (LSSI) adapted our model in Fort Wayne in 2016, so we knew it was possible. But like all things at Cara, we understood that finding the right partners required intentionality. With Stand Together’s help, we built a rubric by which to vet the viability of potential affiliates, and a robust pipeline of prospective expansion partners to go with it.

As we developed this due diligence model, we identified five factors to assess organizational fit (see image). To be truly transformational, we understood that the relationship couldn’t be transactional, but rather, a long-term partnership where we could grow with each other.

Cara’s Partner Selection Due Diligence Mode


We found that first partner in Atlanta Mission, the largest homeless shelter in Atlanta. After three months of due diligence and 10 months of carefully co-creating a model, we launched a program that blended our intellectual property and expertise with theirs. Since starting in July, the program has already completed one cohort and developed partnerships with a half dozen employers ready to hire their participants.

While Cara’s expansion efforts are still new, we are encouraged by how our approach has adapted to different contexts. Both LSSI and Atlanta Mission are faith-based, while Cara is not. LSSI’s population tends to be Caucasian and Atlanta Mission is a homeless shelter – characteristics that we don’t share. Similarly, our two social enterprises – Cleanslate and Cara Connects – have expanded with partners with different models and demographics. And yet, the transformations our partners see in their participants are just as profound as those at Cara. Our guiding principles approach, straight from the Market Based Management (MBM) playbook, has allowed us to flex in different ways to expand how Cara works. This flexibility has also enabled us to learn from our partners, who have the room to adapt and innovate, making us, them, and the whole sector stronger.

As we continue to work with other Catalysts and partners, we recognize the need for a holistic, long-term and proven approach to workforce development across the country. However, affiliation moves slowly – as it must, in order to co-create programming and lift up the culture of each affiliate organization. In order to have the impact that we desire, we needed to build out an additional pathway to scale that could amplify the number of people served and accelerate our learning through trusted partners in markets across the country.

To that end, we are launching a lighter-touch alternative, Cara Institute, a three-day immersive training that exposes organizations to our model, culture, and other practitioners who are willing to share their best practices and best failures. We hope that through Cara Institute and the national Cara Network we are building with these partners, we can create a community of cross-learning for organizations facing similar situations across the country, where we can all walk away with our thinking nudged and our models stronger.

Tom started Cara focusing on one participant at a time, recognizing that each individual is different. We’re doing the same thing through our expansion – adapting our model, one organization at a time, because we know each community is different. While our focus is building out our affiliates and Institutes, we’re learning that we’re doing something bigger too: we’re shifting perspectives on how workforce development can be done.

Sara Wasserteil is Managing Director of Expansion and Integration. Aleena Agrawal is Expansion Strategy Manager. Cara has institutes scheduled in September and November 2019, and February 2020. Learn more at www.carachicago.org.

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