Partner Story

Hillside Work-Scholarship Connection

Since Hillside Work-Scholarship Connection (HW-SC) began in New York 30 years ago, its unique emphasis on providing multiple anchors of support has helped thousands of students graduate from high school and transition to postsecondary education and careers. In 2008, after an enthusiastic response from local school leadership and community stakeholders, Prince George’s County, Maryland became HW-SC’s first extension site. VPP recognized the high graduation rates and other positive outcomes HW-SC yielded in the county and decided to make an investment in HW-SC. By the completion of VPP’s investment, HW-SC helped over 850 Prince George’s County students stay in school, earn their high school diplomas, and prepare for employment and postsecondary education.

Karene Brodie, Carol Thompson Cole and Michelle Gilliard tell the investment story.

  • Karene Brodie

    Hillside Work-Scholarship Connection

  • Carol Thompson Cole

    Venture Philanthropy Partners

  • Michelle Gilliard

    Venture Philanthropy Partners

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Karene Brodie – Executive Director, Hillside Work-Scholarship Connection: Hillside Work-Scholarship Connection’s limited capacity in the region before VPP’s investment really challenged us to run the organization with a very skeletal staff and operation. It’s tough to plan, establish structure and think long-term and big-picture, while also having to attend college tours to ensure quality, best-practice modeling and delivery of our services with fidelity.

Carol Thompson Cole – President and CEO, VPP: Prior to our investment, HW-SC had a culture of metrics, which was important, but they were also building a strong relationship with Prince George’s County. This was the final investment in our second fund, so we wanted to strategically choose a capacity-building investment that would contribute to our future work in Prince George’s County.

We also realized the value that we could offer to HW-SC – the expertise of navigating the region – that was our secret sauce for this investment. We knew we could help make connections beyond those that they already had. We saw an organization that was high-performing, that we could add value to and help them grow more in the community.

Karene: Working with VPP presented so many great opportunities to leverage existing public and private resources and expand funding opportunities. We wanted a long-term relationship with investors. We wanted to know that, beyond Wegmans, others valued and believed in the work that we were doing over time with young people and could really grow with us over multiple years toward the outcomes and the stability we were seeking.

The most tremendous resource that came as a result of this investment is the infrastructure that we managed to build; including, a strong and locally-based human resources capacity in order to attract and develop strong talent, and a more standardized performance measurement structure for data capture, analysis and recording. In addition to those resources, we received support for growing our model to scale. At the direct services level, the ability to have more Youth Advocates in place and infuse training and technical support without compromising service delivery was key to our fidelity, expansion and innovation.

Michelle Gilliard, Partner, Venture Philanthropy Partners: The major goal that we established together was to strengthen the capacity of the organization to expand the number of youth being served. As Karene mentioned, it had a lot to do with building out the infrastructure with key positions, which included positions such as a chief operating officer and an HR professional.

Carol: It became clear that increasing the capacity of the Youth Advocates was also important and Hillside-Work Scholarship Connection was able to make that case to our board. The other important piece was that as we were building the investment from the business plan, even though we scaled back from HW-SC’s initial high, fast-growing aspirations, people were still concerned whether the growth goals were too aggressive. Another factor was that HW-SC was the first investment of this kind to serve Prince George’s County. There was a real fear that it would be difficult to reach the goal to serve more youth at high quality with HW-SC’s existing capacity.

We spent a little more time in dialogue and actually called an additional meeting to really test that. In the end, it worked out well.

Michelle: Yes, it did. And one of the reasons why is because of the positions we helped put in place. We had to be thoughtful about which positions were most important for an organization that had a headquarters in upstate New York. The organization couldn’t really grow in this new location without having the right capacity of local staff to talk to local employers and the school system. It had to be localized and adapted to the culture of HW-SC in Prince George’s County.

The plan was to grow to serve 870 students over the course of this investment. We helped to manage the milestones, but it was also important for VPP to help HW-SC’s headquarters understand how the local HW-SC affiliate had to adapt to the needs of Prince George’s County. Given our experience with replications and our expansive knowledge of the region, we were able to step in and advocate for the local organization’s operational capacity needed to serve triple the number of students.

Carol: We were able to provide context to HW-SC’s headquarters about the difference in the economies in Maryland and New York. You’ve got to adapt to the realities of the place that you’re in.

Karene: That’s right. It is also important to mention the benefit to HW-SC in Prince George’s County of having the support of the New York affiliates. It was imperative for us to align ourselves with our NY-based colleagues and systems; as well as, regional collaborative efforts and other strong organizations that could support young people, both within and beyond what Hillside Work-Scholarship Connection could offer.

A few of our greatest alignments to date are the partnership we have with the Prince George’s County Department of Social Services, our collaboration with the Transforming Neighborhoods Initiative and the Ready for Work initiative’s youthCONNECT at Suitland collaboration with VPP. These are the ways that HW-SC philosophically likes to operate – connecting to partners and collaborative opportunities that help us do our work, maximizing strengths and avoiding unnecessary duplication in service. It is imperative in this region to do that as early as possible, as often as possible and in the best interest of the students we serve.

Michelle: Another important piece is how the national and local offices work well together. It has been exciting to see that HW-SC’s Business Process Coordinator, who was hired through our investment, is providing training to folks in New York. There is some great learning that has happened here where you can have local capacity on site and you can figure out what the relationship needs to be because there is a tremendous amount of important back office support that’s provided in HW-SC’s headquarters. It’s a back and forth dynamic where both can gain insight from and support each other.

Karene: I agree. Instead of a top-down application to replicating, we’ve now learned that there’s a knowledge share that goes both ways. We’ve been able to leverage the Business Process function; as well as, our human resources generalist, for example. It really has been a rich experience for us to expand how we think about growth. Because we were the first replication outside of New York, we had a lot of strengths drawn from HW-SC’s proven and well-established footprint in New York, and we also had a lot to learn. As an organization overall, we love to learn, grow and to apply continuous learning to our model.

We all come into this kind of work with the desire to support, the desire to change and the desire to impact. As a result of VPP’s investment, we really celebrate our exponential growth with quality- we increased our service capacity for students by 300 percent in three years. The fact that we’ve maintained our outcomes throughout this growth period has been phenomenal. Our local data can now formally demonstrate a seven-year trend on our impact here and the outcomes that we have been able to maintain. We’ve been able to maintain retention rates of students in the program in the high 90s. We also have promotion rates at around 96 percent and a four-year, on-time graduation rate of 98 percent.

Michelle: It is exciting to see HW-SC’s growth and achievements over time. It is impressive that HW-SC, with a high-touch model and being school-based, has been able to bring in many additional schools and serve a larger number of students in a short period of time. The organization is even stronger than it was when we started our investment. We helped it to grow and put it on a good trajectory to maintain and deepen the work in the County. Hillside Work-Scholarship Connection is exhibit A of a high-performing organization. Karene is an excellent leader who is passionate and has worked diligently to connect with the right people and places to move the organization forward.

Karene: Thank you Michelle. A final piece about this investment that I want to highlight and that I really appreciate is the value of leadership. I’ve learned and grown a lot throughout this journey. I tell my team sometimes that “My role is as a servant leader, but yours is especially cool because you all get to work so closely with the young people.” I appreciate VPP’s emphasis on the importance of leadership as much as the model and the work itself. It really does inspire you to do more and know the efforts lead to impact and appreciation.

We appreciate that you have invested in both my own and our team’s collective professional development.

Carol: One of the things that people say is that we select well and we did just that with Karene and Hillside Work-Scholarship Connection. If Karene had not been there, we probably wouldn’t either. To see that she shifted and pushed and pulled to achieve big aspirations has been amazing to watch and be a part of. She understands how to move a vision forward without giving up. I believe that’s a big part of the reason VPP’s investment in HW-SC has been so successful.

Investment Highlights

Hillside Work-Scholarship Connection of Prince George’s County identifies promising middle and high school students at risk of dropping out and provides them with academic support, mentoring, skills training, and the opportunity for part-time work. Students are paired with a professional youth advocate through graduation and up to two years post-high school. Full-time, school-based youth advocates serve as mentors and role models, working with students to address their individual needs and the obstacles impeding their success. Services include targeted academic supports, such as tutoring, test preparation, college readiness, academic skill building, year-round academic enrichment, and after-school programming.

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2014 – 2017 | $1,950,000


In Prince George’s County, only 71 percent of low-income students graduate on time. For those students who participate in the Hillside program and are employed by a Hillside Employment Partner, that jumps to 93%.

VPP’s investment will be used to help Hillside: