Homebrewed Heart with Cherilyn

Cherilyn Holloway - Development and Communications Manager at The Haven Home

Cherilyn joined The Haven Home in early 2025 with a passion for uplifting mothers in need of support.

As we all know, non-profit organizations are a beautiful and unique business structure that centers the idea of giving back and uplifts communities. However, it is less common knowledge that non-profits are not hard to come by. Although it is an often misunderstood, undervalued, and unnoticed industry, there are approximately 1.8 to 1.97 million registered non-profit organizations in the United States alone, making it clear that there are no shortage of causes to support or ways to get involved with our local communities.

Instead, what we lack is the knowledge to make informed decisions on what organizations we each feel a personal connection to and ways to support them. Cherilyn Holloway, the Development and Communications Manager for The Haven Home in Cleveland knows this struggle well and has made it her mission to connect individuals with her cause and ensure that they leave the experience having learned something new.

Cherilyn was born and raised in Oberlin, Ohio which she describes as an extremely diverse community. This small, liberal arts college town fosters the perfect blend of love and acceptance where all of its residents have only known the strength and celebration of one's differences. Leaving Oberlin for college and some of her early career, Cherilyn got a front row seat to how her tight knit community didn’t quite mirror the openminded-ness of the rest of the world.

Her small town upbringing was far from sheltered and Cherilyn was exposed early on to people from all walks of life with so much culture and community to share. Her father worked as an air traffic controller which landed her family in this culture rich area and she learned a lot about her own personal history as well with Oberlin being a part of the Underground Railroad. She went on to tell us that it not only felt that she was pulled to give back and make a difference, but that it truly felt discouraged by the community to not have an injustice or effort that you wished to help solve.

“Any possible way you can think of people being diverse, Oberlin has it. So for me, I always felt this call to serve others in some way shape or form. I even realized early on I was extremely blessed to have an economic status that was different from some of my friends with my dad being a government employee. But because of that I was able to see that if I want to go out to eat, I have to take enough money for my friends too and I had very generous parents who understood that and wanted to share what we’d been given,” she told us.

After attending college at The Ohio State University and eventually moving on to earn her masters in human service, Cherilyn was honest with herself about her dislike for the classroom and instead focused on the joy she felt from an internship opportunity that allowed her to work for a non-profit after school program in Columbus. This unpaid position gave her her first lesson in nonprofit management and the rest was history.

Cherilyn and Cindy (Executive Director of The Haven Home) at Woman Up Cle's Homebrewed Hope fundraiser in April 2025.

Cherilyn has now been working in the non-profit world for 30 years and has almost exclusively spent that time serving women and children. She has lived and worked in Ohio, DC, and Maryland and has had roles as a private school teacher, development specialist and executive director at a pregnancy center, and eventually landed in her current position. From these experiences, she has become an expert in non-profit development and communications and her skills make her an asset to every organization she finds herself a part of.

Over her time in this space, she has truly zeroed in on her own strengths and applies them to her daily work. Cherilyn said, “I found that what I like to do most is help facilitate effective communication. I truly believe that if you can facilitate effective communication and bring awareness that the development side of bringing funds comes on its own because you're connecting people to a cause that they already care deeply about, but they just don't know it's there.”

Her past experiences teaching children ultimately gave her insight into communicating and connecting with parents and her work in pregnancy centers and after school programs further connected her to the work she felt called to do. However, it wasn’t until she received encouragement for her skills that she knew she was capable of taking on a more administrative position in these organizations.

Connecting with individuals to speak about how the organization can help them along with what their personal needs and barriers really are. Upon returning to Ohio, Cherilyn knew that one of the largest struggles for mothers being able to take care of their children was finances. “I was actually hired as an Americore Vista to come up with some financial literacy programs for a community service center in Oberlin and that’s how I ended up creating an entire curriculum and using it to teach larger material companies about their onboarding process,” she told us.

After spending the next three years at a pregnancy center in Elyria, Cherilyn found herself ready to move on and tackle the larger non-profit issue of visibility and connection. Knowing that the communication aspect of her work was her calling, she started a job with an international marketing company that taught her the social media and communication skills she would later use to help non-profits reach the public.

Cherilyn said it best, telling us, “ I always say my goal is to turn a light bulb on. So if nothing else, if people walk away from me and they can say, ‘I never thought about it that way’ then I feel like I communicated something very effectively.”

Developing meaningful connections with mothers and the community is a top priority of Cherilyn.

Her drive to spread resources mixed with her understanding of the ins and outs of non-profit work eventually made her the perfect candidate for her current role as Development and Communications Manager for The Haven Home. The Haven Home is a Northeast Ohio non-profit that provides stable housing options for local pregnant and parenting women experiencing homelessness. Since 2017 they have expanded and adapted to the communities needs and now provide longer-term transitional housing and resources for up to 14 families.

Cherilyn’s role at The Haven Home began in February of this year and has already settled in to creating change in our community. Her work helping mothers is not only impactful, but necessary in ensuring equal access to safe housing and financial stability.

You can easily see that Cherilyn’s own experiences have led her to her work with The Haven Home. She told us, “I do not believe that everyone can have a dream and achieve it without support from others. I do believe that there are systemic barriers to that and what I have found as a mother, the way I have been able to achieve my dreams is with the support I've gotten. So if I want to encourage particularly more black women to say yes to motherhood, for the sake of rebuilding our community, then we have to break down some of those barriers that are making them feel like they can’t and rightfully so.”

Affordable housing is an issue for all and Cherilyn knows that it can be a first step in rebuilding a life and securing safety for a family. She said all of this made starting at the Haven Home the natural next step for her and now feels the impact of her efforts in her own backyard. Her day to day role includes connecting with donors, volunteers, and community partners along with finding the best way to leverage communications and resources to build what The Haven Home is trying to build.

Cherilyn cited lots of CRM (Customer Relationship Management) software, design programs, newsletters, and social media in her daily operations and hopes that as her position grows, she can begin to get out in the community and connect with others a bit more. Although she also joked, “Having me out in the community is good and I like it but then I have to come back and track all that I did and all the other work is still there. So I always joke that I’m mostly remote so I can stay focused and get things done.”

Cherilyn and her daughter smiling at the ball field.

We found this to be an interesting point made by Cherilyn regarding roles within a non-profit organization. Connecting back to the lack of knowledge that the average individual has regarding non-profit work, there is often a misunderstanding that to do this work, you must be outgoing, outspoken, and physically out in the community making a difference with your own two hands. This chat and hearing Cherilyn talk about the importance and impact of her role, which if she’s not careful can station her behind a desk, reminded us that administrative roles and non customer facing positions do exist in non-profits for those who seek them.

It serves as an important reminder that not only can anyone find a fit for themselves within a non-profit organization the same as they would in a corporate setting, but that the barrier of knowledge is truly what puts non-profits in their own category and makes them seem unrealistic for some. There is a clear disparity between those who are interested in non-profit work and those who have no idea that it could be an option for them. These are exactly the situations that make Cherilyn’s job so essential, being sure that anyone and everyone knows about non-profits, the work they are doing, and how the individual themselves can get involved.

We went on to talk to Cherilyn about how Cleveland has stacked up to the other places she has found herself making change and if the community here feels different in its support or acceptance. She shared, “I found that Cleveland is very supportive. Way more people know each other than I thought would know each other. Way more people have connected with us and we've had relationships with the Cleveland Cavaliers, the City of Cleveland, different mayors and congressmen, all the banks, and people really want to help.”

She really encouraged other non-profits to seek out the businesses or corporations that seem out of reach saying that they all have people within them who have the heart to help. She added, “Everywhere I named has a sector of their company that is solely for helping non-profits where they call it ‘community engagement’ or ‘community outreach’. Their job is to make those connections and help find out what the needs are so when people actually reach out to them it makes their job easier.”

Cherilyn continued to talk about the benefits of connecting with others and how Cleveland's welcoming spirit has helped in her work saying, “It's been really great to feel like I could always pick up the phone and call somebody if I have an idea or question. Any type of advice, people in Cleveland are so responsive and just want to help. Clevelanders really do just have these big hearts that want Cleveland to do well. There are so many good organizations doing good work.”

Although it never surprises us as Cleveland lovers, it is always so encouraging to hear that people feel understood, accepted, and uplifted by individuals and businesses in our community. The Cleveland magic really is real and each time we connect with someone new, it is such a thrill to hear how the sense of community that is so unique to our city has positively impacted them and their story or work.

Outside of work, Cherilyn enjoys quality family time and celebrating life's accomplishments.

Things came full circle when we asked Cherilyn about something she wishes people better understood about non-profits and her work. As we have said in so many different ways, communication is key to making the community resonate with non-profit work and get involved. With getting involved, there are unlimited ways that someone can become a part of the cause including volunteer work, career positions, and donations.

However, along with this miscommunication comes a common misconception. Many people assume that non-profits will take help in any form they can get it, and while that may be true, those looking to make true and lasting impact should always dig below the surface level and reach out to find what an organization's needs really are and aim to contribute to those.

This is where Cherilyn’s piece of advice shines. She told us, “The best way to support a nonprofit that aligns with your values is to find out what they need. A lot of times when we think of, for example, The Haven Home or unhoused women, we think ‘okay, they're homeless so clearly they need toothpaste and toothbrushes and socks and underwear.’ Because we are a transitional home and our residents are not transient, we actually don't.”

She continued to explain this lapse in judgement saying, “I have to imagine that there are other nonprofits who would love that particular donation. So what I have found is that so many people get an idea that they want to help but it would have been more helpful had you called us and asked us.”

This happens often with the misunderstanding of what a non-profit can benefit from and people often are only willing to get involved in certain ways. Whether it be a monetary donation, physical donation, volunteer time, or a more permanent position, although the initial organization you have in mind may not be in need of what you have to offer, there is almost certainly another one who is. Taking the extra time and effort to seek out a good fit that aligns with your values, time, energy, and effort can make all the difference and create a mutually beneficial connection that leads to lasting change.

Finally, we asked Cherilyn what she sees for her future and that of The Haven Home. Although her time with the organization has been brief so far, she knows that it will continue to grow and expand as the years pass by and she intends to continue being an important part of that journey. The vision of The Haven Home is to expand and offer some next-step housing and see what that could look like for residents. The non-profit has been around for eight years now but its new organization model is only a little over a year old and so there is lots of change and transition still happening each day.

Cherilyn went on to say that although she typically feels that she can see herself leaving a role after a few months getting to know it, she recently realized that her feeling of moving on, doesn’t apply to her position at The Haven Home. She said, “I'm at the place where everything that I've learned for the last 30 years is finally all being used and I'm confident in using it. But then I'm also excited because there's so many possibilities for the future where I don't know what's going to happen and it can only go up, it can only get bigger, it can only grow.”

Cherilyn Holloway is the perfect example of ending up where you are meant to be, and how non-profit work can truly be for anyone who cares enough to make change. She is the embodiment of a life long giver and her work over the last 30 years in non-profit organizations proves that dedication is the key to lasting change and meaningful efforts. Communication really is at the heart of all non-profit work and with that being her job requirement, Cherilyn deeply understands its importance, impact, and inspiration. Her dedication to helping mothers and families navigate the hardships they face and overcome the barriers in their way truly sets her apart.

Working with her and The Haven Home on our Homebrewed Hope Tea Party Fundraiser in April was deeply rewarding and it was a pleasure to not only connect with Cherilyn again, but hear more about the epic story that has led her to such a wonderful organization here in Cleveland.