Leap Voices is a new series lifting up the importance of equity and high performance by sharing the voices and experiences of Leap Ambassadors.

Standing in the Gap: An Advocate for Student Parents

Samantha Sherrod • March 2023


Leap Ambassador Reginald Grant thought he’d become a fourth-grade teacher, not an organizational leader. Yet for more than 20 years, he has provided direct services to youth and worked in funder roles to support organizations serving young people. Today, Reginald is the Chief Operating Officer of Generation Hope, a national nonprofit that provides direct services to teen parents pursuing post-secondary education and that advocates for student-parent educational equity. Leap Ambassador and support team member Samantha Sherrod spoke with Reginald about what inspires him, his role at Generation Hope, leadership, high performance, and what it’s like to be a “Black unicorn” in the nonprofit world.



Samantha: There’s a common thread throughout your work: youth. What inspired and continues to inspire you to work with youth at Generation Hope?

Reginald: I learned the importance of caring for youth while growing up in the Kayton Homes public housing community in Savannah, GA. The older people in my community taught me this principle, which has shaped my work and who I am as an individual. I look at myself as a youth practitioner first. Thinking about the young people in my community is at the core of everything I do.

I know firsthand what it’s like to be a part of a community where teen mothers and fathers need support as they pursue their education. Three of my four sisters had children in high school and were student parents throughout college. With my sisters in mind, I joined Generation Hope to advocate for student parents and dismantle the challenges they experience. The resilience in young people to overcome obstacles inspires me, and I’m honored to provide a service, stand in the gap, or just listen to them.

Samantha: Describe Generation Hope.

Reginald: Generation Hope is a national nonprofit organization with headquarters in Washington, DC. It was founded by teen mother Nicole Lynn Lewis, who was pregnant when she started attending the College of William and Mary. The campus environment was geared toward high school graduates with no parental responsibilities. Nicole created Generation Hope to ensure that teen mothers and fathers pursuing their college degrees don’t face the roadblocks she encountered, have opportunities to succeed, and experience economic mobility. We do this work by engaging education and policy partners to drive systemic change while providing direct support to student parents in college and their children through holistic programming. We are a two-generation solution to poverty. More than 75 percent of our student parents are first-generation college students and most are considered low-income.

Samantha: What roadblocks do student parents face?

Reginald: Although more than one in five college students are raising children while attending school, student parents are an invisible population on college campuses. Post-secondary institutions aren’t collecting data on this population as they do for veterans and first-generation students, which makes it difficult to design policies to address the issues of student parents. For instance, higher-ed leaders aren’t leveraging Title IX to provide aid to student parents. Less than two percent of teen mothers who have a baby before the age of 18 earn a college degree before the age of 30. But if we disaggregate that data by race, we know that the majority of those teen mothers are women of color who are experiencing high levels of debt once they graduate, if they graduate. Ensuring that these women have support is critical to their success. Attendance and no-child-on-campus policies in higher education often fail to consider the challenges faced by student parents, especially when their child is ill and they cannot attend classes or when they don’t have access to affordable, quality childcare. Furthermore, being a person of color and a student parent can add an additional layer of oppression to an already challenging landscape.

Samantha: Describe Generation Hope’s flagship programs and their impact.

Reginald: Generation Hope’s flagship program is the Scholar Program, a mentoring program with wrap-around support for teen parents up to the age of 25 in the Washington, DC area and now growing to New Orleans, LA. We currently serve 142 teen parents who have committed to attend at least two classes each semester at either a two-year or four-year college. Each Scholar has a Hope Coach [case manager] who helps them navigate the collegiate experience, connects them to resources like affordable housing, and facilitates emergency assistance from Generation Hope. Scholars are also mentored by a community member who contributes to the Scholar’s annual tuition in the amount of $1,200 for a two-year school and $2,400 for a four-year school. In addition, Scholars have access to life skills training, parenting classes, and other workshops to support them on their college journey.

We’re eliminating the stigma of having a child while in college and transforming the higher-ed culture in support of student parents through FamilyU, a two-year, cohort-based technical assistance program for colleges and universities to improve student-parent outcomes. We’re working with 11 universities nationwide, including two Historically Black Colleges and Universities (HBCUs). Upon completion of FamilyU, participating higher-ed leaders will have data instruments to identify student parents on their campuses and communicate with that population to determine how to meet their needs. They’ll also evaluate the policies on campus that hinder student parent success and ensure that the group is recognized and supported. For example, they create recruitment materials that reflect student parents, develop training for all staff and faculty that focuses on the experiences of student parents, and make resources available to student parents, including diapers and toys for their children while on campus, to create a more inclusive environment.

We support 41 preschool- and kindergarten-aged children of student parents through Next Generation Academy, which focuses on literacy and social and emotional development. In this program, the student parent and their child are matched with a family in the community to increase their social capital, participate in monthly home visits to support the child’s cognitive and social-emotional development, join family dinners with other Scholars and children, and receive brand new  culturally diverse books. Parents of students in the Next Gen program also receive a monthly stipend to help with childcare or other enrichment activities.

Generation Hope’s graduation rate is on par with the national average for all college students whether they are parenting or not. When disaggregated, we see our Scholars thriving in comparison to other students.  For example, the six-year graduation rate for Black student parents in our program is 52 percent, eight percent higher than the national average of 44 percent for all Black college students. The six-year graduation rate for Latinx student parents in our program is 69 percent, 18 percent higher than the national average of 51 percent for all Latinx college students. Student parents involved with Generation Hope are doing well, and once they graduate from college, many are on the track to experiencing economic mobility.

Samantha: Describe your role as Chief Operating Officer (COO) at Generation Hope and a current project that excites you.

Reginald: As COO, I ensure we have a sound human resources system, financials, practices, and policies for our organization; that our CEO’s directives are being met; and guide our work using our race-equity blueprint. Because this work is dear to me, I’m a part of its design and execution. I’m involved with our direct service; I can often be found with the program team, training mentors on how to build authentic relationships. My immediate connection to our work helps me better understand the Scholars’ and the Hope Coaches’ experiences, thus creating an inclusive and equitable strategic plan.

I am leading our expansion to our new Scholar Program location in New Orleans, LA. The community is committed to transformation, equity, and giving everyone a chance, which is critically important as New Orleans has the third highest teen birth rate in the nation. Just like in the DC region, we are being intentional about how we grow our work in New Orleans, inviting local business leaders and education champions to the table who are not always represented when it comes to building new things. Many of them are Black and Brown business owners, educators, and philanthropists who are giving back to the community and might serve as our first mentors to our new class of Scholars there. We’re excited about offering our services to New Orleans and continuing to help young parents transform their lives through higher education.

Samantha: Congratulations on Generation Hope’s expansion and serving more people than ever under your leadership. Why has Generation Hope been successful?

Reginald: Student parents are pivotal to our success. When we created our strategic plan at the start of the pandemic, we involved them. If student parents don’t like something, our team focuses on their feedback and returns to the drawing board. Student parents give us insight into how they experience Generation Hope, what we need to improve, and where they don’t see themselves in programming and policy efforts. They are also involved in the hiring process. A student parent participates on every interview panel for our programming positions, and they hold the same amount of power as a staff member. It is our practice to always have student parents ask a candidate the first question and contribute first when we’re discussing a candidate after the interview. They’re the experts of Generation Hope and are compensated for their insights.

We don’t just serve student parents; they are leaders within our organization. And they are excited to be ambassadors of this work. Recently Generation Hope was featured on Good Morning America, and a Scholar talked about how life would’ve been more difficult without Generation Hope. While this is a testament to Generation Hope’s work, we can’t take ownership of that Scholar’s success. Student parents are resilient and, therefore, will be successful in some capacity. But, with Generation Hope, they voiced their needs in a supportive space, which made the journey a little less challenging.

Samantha: Describe your leadership style and how you operationalize that approach.

Reginald: I believe in servant leadership, which involves putting the team first. However, during the pandemic, I realized I often excluded myself when ensuring the team was healthy. As a result, my leadership style now embraces honoring my talents, giving myself grace, and pursuing self-care.

With this new leadership approach, I prioritize self-care and mental health for the team at Generation Hope. We have destigmatized the shame around mental health and asking for support. Starting in the pandemic, we allocated at least one self-care hour to each team member per pay period. During this sacred time, they can tell their direct supervisor or external stakeholders, “I won’t respond to you during this hour, but I will respond to you when I return.” Also, we hold weekly check-ins with each team member and prioritize asking, “What’s going on with you and how’s your heart?”

Often folks say, “Leave it [what’s going on with you] at the door.” But as a Black man in this work, I can’t leave my identity, experiences, and family at the door. Those aspects of who I am impact the way I work. So I’m creating an organizational culture where team members can be honest, gracious with one another, and feel comfortable sharing what’s honestly going on with them without feeling like they will be reprimanded or shamed.

As a man of color from public housing, talking about mental health is considered a third-rail issue. But our team can’t be healthy if we don’t prioritize mental health in the systems and processes impacting the person.

Samantha: What does high performance look like in the context of your work?

Reginald: Being a high-performing nonprofit is about accomplishing the goals that you set forth. But it’s also about how you do the work. And that’s why our commitment to race equity is important. Generation Hope is an anti-racist organization with a race-equity outcome and strategies based on our roles in the community. We have modified the Leap Ambassadors’ Performance Imperative to include eight pillars, not seven, to fit our organization. Race equity is our eighth pillar. We’ve used resources like Awake to Woke to Work to forward this work. Our eighth pillar helps us determine where we’re coming up short as we strive to be an anti-racist organization. We are committed to anti-racism beyond the statements we place on our website or social media. Because we primarily serve people of color, we cannot support a student parent without focusing on race equity. For this reason, we have a diverse leadership structure, frontline staff, board, and volunteers so that student parents can see themselves in Generation Hope. And everyone must attend race equity training to continue to learn and devise audacious strategies to support student parents.

Samantha: You identify as an African American cisgender man and you serve in leadership at a nonprofit, which is rare. What’s the experience like for you, and who has influenced you?

Reginald: I saw myself as a fourth-grade teacher. But when I joined the social sector, I approached the work from a different lens. Because I once received nonprofit services, my goal was to uncover and dismantle systems creating barriers for people to experience their greatest potential. So I listened to and co-created with the people most impacted by the work; considered the community’s culture, history, and institutions when designing strategies to support a community; and wasn’t afraid to be innovative. I’m the most reluctant leader. And the narratives around my intersecting identities say I shouldn’t be in a position of power. Sometimes I refer to myself as a “Black unicorn,” because high-level leadership in this field, especially working with children and youth, has involved white women leading the way. I’m often the only Black man in the room. However, I am honored when Black men and women see me and say, “I’m so proud of you.”  And I think, “I’m like you, if you only knew.” I wish my younger self could see me now and know he’ll be okay. It didn’t always feel that way when I was experiencing aggression and micro-aggressions because of my skin color.

I’ve been blessed to have some powerful Black women and men mentor me. They taught me to lead with my expertise and skills but to show up first with my heart. Terry Sims Snipe saw gifts and talents in me I didn’t see in myself when I was a youth counselor for the Housing Authority of Savannah, GA. Johnnie Gage, former Vice President of Programs and Finance at the Milton S. Eisenhower Foundation, introduced me to this career and taught me to navigate certain conversations and rooms. He’d say, “Reggie, when the elephants fight, the grass suffers. Remember in our work that children sometimes are the grass.” As I sit at decision-making tables, I remind myself of that African proverb that the weak get hurt in conflicts between the powerful. Deborah Scott, who ran youth development programs in Philadelphia, taught me to be honest with [young people] about my leadership experiences to help build their skills and resilience.

Today, I’m honored to serve a leader like Nicole Lynn Lewis, who has invested in me and sees me as a full partner as we transform student parents’ lives and their families. Leap Ambassador Art Taylor helped prepare me for leadership as I watched him serve as board chair and masterfully lead a national organization. Finally, I’m encouraged by my great-great-grandmother Blossom Hamilton, a Gullah Geechee woman, who’d say, “When does a lion get tired of roaring? A lion roars because that’s what it was made to do.” She inspired me to find what pushes me forward—working with youth who look like me. That’s what I was made to do.


Although Reginald isn’t a fourth-grade teacher, he still teaches every day. He may be a “reluctant leader,” but his leadership makes a difference in the lives of student parents, their families, and future generations.



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