How to Lead a $30 Million Dollar Nonprofit and Turn Big Ideas Into Scalable Systems

Childcare is not a personal problem. It is an economic one, and the system built to support it is underfunded, understaffed, and breaking down.

On She Built It®, Jennifer Cowan, CEO of Connections for Children, a $30 million nonprofit serving the West Side and South Bay of Los Angeles, shares what it actually takes to lead a mission-driven organization through a pandemic, wildfires, a headquarters move, and a national childcare workforce crisis, all while continuing to grow. Jennifer talks about how she turns big ideas into scalable systems, what it takes to align public, private, and community stakeholders around a common goal, and why resiliency and flexibility are the most critical leadership skills in the nonprofit sector today. She also speaks to the founding of New York City’s first Expanded Learning Time model (now replicated nationally) and what leaders need to understand about building something designed to scale.

This is a conversation about systems, leadership, and what it looks like to keep showing up for families when everything around you is changing.

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Transcript

SPEAKER_01 0:00

Childcare is so important for women, but also for the economy, because if people can't find a safe, affordable place for their children to work, they're not going to go to work or be consistent or productive or be distracted. That's why I love what we do and I'm still connected to the mission because I believe it is critical for family stability, mobility, and also for early childhood development.

SPEAKER_00 0:29

I'm Melanie Farr. Welcome back to the Cheaplet Podcast, your go-to place to empower you to live the life and business that you crave. I'm here to talk about everything from having the courage to make life and career leads to the details of how to lead effectively, create successful teams, implement strategies for growth, and infuse tech innovation. I'm here to celebrate your wins and navigate through your challenges. I live in the city now, but I grew up in a town of a thousand people. I've navigated major life leaps, a senior-level corporate career, worked in professional sports, and now as a successful entrepreneur who loves business, technology, family, and making meaningful connections with you and the She Built It community. I also love a good workout and dose of self-care. Magic happens when we focus on the part of ourselves and our business that brings us joy. So turn up the audio, open your favorite notes app, grab your favorite drink, and here we go. Welcome to She Built It. Thank you for being here, Jennifer. You lead a $30 million organization. What does it take to operate at that scale? And what leadership skills matter most?

SPEAKER_01 1:38

We are fortunate in that we have an incredible leadership team and larger staff to help us implement the work that we do. So for me, having a team of leaders that I can collaborate with and brainstorm with and delegate to is key for the success of our organization. My approach in leadership is that one person can't achieve or implement everything on their own. So I think that's been the key to our organization even before I stepped into this role, having a strong team, being able to deliver our programs and services.

SPEAKER_00 2:19

And even as good leaders, we're not always good at everything. And so it's so good to have those teams around us that can support us in the areas that they're best at. Exactly.

SPEAKER_01 2:29

That's something I've definitely learned throughout my leadership journey is finding colleagues and other leaders who complement your skills. Of course, you need to be able to collaborate and work together, but you don't all want to have the exact same skills, exact same approach or background, because that is where you might get stifled and creativity and new ideas or new approaches will not come to light because you're all of the same mindset and from the same background.

SPEAKER_00 3:01

That's what makes a good leader is being able to look at yourself. It's not always easy. And in the beginning, it's hard being able to look at ourselves and say, okay, what am I good at? And what do I want to do every day? And then surrounding yourself with that team that is good at the things that maybe you don't want to do or maybe we're not the best at as a leader. Share with us more about who you are and what Connections for Children does and the core challenge that you're solving every day.

SPEAKER_01 3:26

So Connections for Children is a nonprofit organization. We serve the West Side and South Bay communities of Los Angeles County, helping families find and pay for quality child care that meets their needs. So we do that a few different ways. We help families navigate their options for child care and early learning so they can figure out what approach is going to be best for them. We also are able to access financial resources for low-income families so that they can afford the type of care and support that they need. So we work very closely with the child care providers and early childhood educators throughout our region to make sure that they are supported in their practice so that they continue to stay in business in the workforce, doing their best work and connecting families who are looking for childcare. That's what Connections for Children exists to do. And we are funded primarily through public resources, so state, local, federal dollars. So a lot of our work is also around awareness and advocacy so that people understand the importance of public investments in early childhood and think about that the same way we invest in other systems that support our communities. So people can work, go to school, support their economic stability.

SPEAKER_00 4:58

And this is a big conversation among women and men too. But around women, when we have kids, it's how do we have our kids? How do we care for our kids? How do we continue working? Maybe we love what we do when we want to continue working, and also have the opportunity to have a family.

SPEAKER_01 5:14

Yes. And I think something that is so important to remember is that childcare, it is so important for women, but also for the economy, because if people can't find a safe, affordable place for their children to work, they're not going to go to work or be consistent or productive or be distracted. I definitely think about that in my own career journey. If I hadn't had choices that felt comfortable and accessible for my own daughter, I wouldn't be in the role that I am now. So regardless of your economic circumstances, navigating those childcare options is very stressful and complicated. So that's why I love what we do and I'm so connected to the mission because I believe it is critical for family stability, mobility, and also for early childhood development. The opportunities that our young children get in quality early learning environments really sets them up for future success. And I think about for my own daughter who's now about to head to college, those early learning experiences were just so formative for her and the relationships that she developed. And I'm so grateful for the educators and caregivers who help provide those to her, in addition to what we did as a family.

SPEAKER_00 6:43

And as a mom and a parent, we can show up and do our best work when we know that our child is safe, when we know that our child is in a good place and going to be well taken care of. Right. You are known for turning big ideas into systems. How do you take something from vision to execution in a way that actually works at scale?

SPEAKER_01 7:01

I love a messy brainstorm. And I love working with colleagues who are comfortable in that mess, and then we can work together to figure out how we operationalize something. So I always love to start with what is our ideal scenario? And then we can think about okay, what are the resources we have? What are the constraints? What is possible now? For example, at Connections for Children, one of our goals was to increase the number of families and childcare providers that we're interacting with in the South Bay, which is part of our service area. We're better known in other parts of our service area. And so we started to think about okay, what are the program services that can most easily be replicated or better promoted in one part of our geography? So we were able to replicate our family time early learning program. We knew it was already really successful in Santa Monica, and we launched another version of that in Torrance. So the first time, a couple families came, the next time a few more families came, and now it is a thriving program that we're thinking we need to even expand further because of the demand. So I think it's also being patient and being comfortable with the slow build or success. We also decided to create a learning festival in the Torrance community to also bring awareness. So bringing together childcare providers, community partners, families to learn more about our work. And so we're seeing that was a way to also build awareness of the other services we support. And now we're seeing an increase in enrollment in some of our other services that we provide. So thinking of our larger goal and wanting to just increase our reach and impact in a particular geography. So having some strategic initiatives and building on what we already know we do well, we've been able to accomplish that.

SPEAKER_00 9:07

I love that you say a messy brainstorm. I'm going to use that one. And we have so much coming at us today with technology that community and being in person is now becoming a really big part of growth. It's so smart of you to take it back to community and in-person events and while also looking at the larger picture.

SPEAKER_01 9:28

Sometimes, especially for what we do, it's hard to see the impact or trust over the phone or over an email that our organization has the knowledge and resources that a family or childcare provider is looking for. But when you do make that in-person connection, it adds a level of trust and credibility that unfortunately you can't always communicate through these other platforms. And of course, when you're thinking about your child, you really need to have that trust and feel like you're talking to someone who has your best interests in mind.

SPEAKER_00 10:10

Yeah. And today, more than ever, we're craving community. You built one of the first expanded learning time models in New York City. What made it work? And what should leaders think when building something designed to scale or replicate?

SPEAKER_01 10:24

That was a really exciting time when I was working at an organization called the After School Corporation. And we had the opportunity to partner with school districts and community-based organizations to build a model to extend the school day so that it was more of a seamless experience for kids who are attending those schools. And I think one of the key elements was partnership and thinking about what resources and skills and talents each of those partners, including our organization, brought to the table. So I love being in a role of facilitating strategic partnerships, thinking how to blend different funding streams, how to adapt curriculum or programming so that it's meeting the needs of the children and the families, but also keeping in mind those who are implementing and delivering the program. So that was a really incredible opportunity. And it was also refinement. It was a pilot program. And so we had a few different models that we were looking at as we worked with different school sites, looking at how the program was structured, how it was staffed, the cost per participant, and what the outcomes were in terms of attendance, engagement, feedback from those who were working in the program. So we're we were able to take that information and continue to refine the program model.

SPEAKER_00 12:01

And that's really great leadership because as leaders, as entrepreneurs, we're constantly refining. And we always have to say, okay, what's working, what's not working, and what shifts can we make along the way.

SPEAKER_01 12:13

I think it's hard when you've put so much time and effort into something or a project or resources to then get to that point to recognize, okay, it's not working or we're spending too much time. We need to figure out why we're stuck. And sometimes saying, okay, we need to pivot or we need to end this project and let's start over. Let's think differently. But I think that can be really hard, especially when your heart is so into what you want to accomplish.

SPEAKER_00 12:43

Yeah. And another part of leadership is saying, this isn't working. I'm gonna need to let this go in order to move on and create something better. Yes. Childcare is one of the biggest barriers to workforce participation. From your perspective, what is broken in the system and what would it take to fix it?

SPEAKER_01 13:01

We really need to recognize that childcare providers and early childhood educators are essential and experts in their field. And we need to pay them based on that expertise and value. We know that so many people get into this work because they care about educating and developing our next generation. They care about young children, but they can't make ends meet themselves. They are not recognized as the professionals that they are, and many of them leave the workforce. And now we're seeing so many are not entering the workforce because it's not a desirable profession. And in some cases, you could make more money working in retail or food service. And so it's such a critical workforce, but it's shrinking. And a lot of that has to do with compensation. So that is one of the biggest issues. And it really needs to be a public responsibility. Of course, families who have resources to pay contribute to that as well. But right now, when you think about the tuition for childcare or preschool, while it feels exorbitant, it does not cover the full cost of care. And so that is really the number one piece that we need to invest in our early childhood educators and that infrastructure so that it is affordable, sustainable, the same way we think about K through 12 and higher education.

SPEAKER_00 14:42

My mother had a master's in education. She was the first in her family to go to college, first to have a master's, taught kindergarten for 29 years, and she was lucky enough to be home with me for the f first five years and then go back to school and go back to education. But I am a twin mom. And I think about when my twins were born and wanting to continue to work and wanting to go back to work. And you think about from making sure that your child is well taken care of when you go back, all of the there's so many layers there to think through from wanting to work yourself, having to work, and then also making sure that your child is getting the best care.

SPEAKER_01 15:24

And then that trade-off in terms of the cost versus what you're making going back into the workforce versus what you're paying and kind of the trade-offs there, which can be really tough. Challenging. Yeah.

SPEAKER_00 15:37

You work across public, private, and community stakeholders. How do you align those groups and still move decisions forward?

SPEAKER_01 15:44

Working with different stakeholders when we come together over a common goal or priority, that's when we're able to make progress and work together. In the city of Santa Monica, I think there are some great examples of cross-sector collaboration where we have the city, the school district, community colleges, business owners, the chamber, nonprofits like Connections for Children coming together because we all recognize that investing in young children is essential for community and economic well-being. So we have that common goal where we're coming together and then determining what each of our leverage points are or our role in advancing that goal. So for us, it is programming, but we can partner on advocacy. We can think about different policies or identifying resources together versus private and public resources to be able to advance our goals. When we're working cross-sector, we have to have a common goal. And I do believe everyone cares about the well-being of children and families.

SPEAKER_00 17:05

It does take a public and private collaboration. It does take that. And our families and children, and it's what life is all about. Yes.

SPEAKER_01 17:16

And I think we're seeing more interest among business leaders and the private sector in supporting children and families because they do recognize it's related to the success of their workforce, recruitment, and even the community that businesses serve or where they're situated, that child-family well-being is critical for their success as well.

SPEAKER_00 17:44

And even if you're someone who chooses not to have kids, children and families are still part of the surrounding community.

SPEAKER_01 17:51

Since I have started in this field, I've seen an increase in interest and commitment among business leaders and businesses to support employees with young children and families, and seeing that in their benefits as well as their sort of policies and practices, because they recognize if they want to recruit and retain their workforce and support them, that's something that they need to do, especially these days when there's so much more flexibility and options for employment. So that that is becoming a recruitment and retention strategy for many. So if you're able to have some flexibility in attending to your family needs and prioritizing those, you're actually going to perform at a higher level when you're in the workplace too. So I think that's something I try and model in my own leadership of recognizing that and supporting my staff to the extent that we're able to so that they feel like they can bring their full selves to work and not be worried about what's happening at home.

SPEAKER_00 19:50

When impact touches families, education, and the workforce, how do you measure success in a meaningful way?

SPEAKER_01 19:57

We look at impact a few different ways. Of course, we want to look at the number of families and children that we're reaching. So we're looking at how many people have been connected to early learning and care opportunities, how many childcare subsidies, it's our tuition assistance, how much money are we putting back into the economy? How are we seeing changes in parent-child interactions? So we survey families to get a sense of how their knowledge and parenting has evolved since they've started working with connections and with our programs. So we also, of course, have a lot of anecdotal stories too about how our resources and connections have impacted families in terms of giving them confidence to be able to go back to work or re-engage in their education so that they're no longer reliant on a childcare subsidy because they've been able to advance in their career. So we have a lot of different measures for how we've been able to help families advance in their personal and professional goals and overall family stability. And then also looking at the childcare workforce and the number of providers and individuals that we're able to train and also sustain their operations. So it's always concerning when we hear about childcare providers who are closing or leaving the workforce. So that's also something that we measure and look at really closely to see what professional development and support opportunities can we provide to help them? And is that support making a difference?

SPEAKER_00 21:48

What does strong strategic leadership in the nonprofit space look like today? And where do you see it needing to evolve?

SPEAKER_01 21:55

I think resiliency and flexibility are so critical. Right now, I've been leading Connections for Children for seven and a half years. And in that time, we've moved our headquarters, we've been through a pandemic, we've been through the wildfires and other instances of community crisis. And I think throughout all of that, and I would say in my conversations with peers, this is verified, needing to be flexible and always stay true to your mission. But how you execute and accomplish that mission may need to change. And you need to listen to what the community needs and how to deliver that because it can change. We've learned that through the pandemic. We've learned that through the wildfires, that, for example, we had distribution events where we had materials and items available for families and childcare providers to help them during these times of crisis. And we had a distribution site at our office, but a lot of people couldn't get to us or they didn't have time because they were managing all these other options. So thinking about, okay, so we need to pivot. How can we go to them? How can we meet them where they are? So I think that's critical in terms of strategic leadership and nonprofit sector, also being really attuned to what is happening at the local, state, federal level because our funding is impact by those policy decisions, making sure we understand what's happening and what we can do proactively to elevate the importance of investing in our communities and what that means and sharing the potential impact if funding and support goes away. So focused on the service delivery and then also the funding and policy piece at the same time, which is all evolving all the time.

SPEAKER_00 24:04

And that list that you mentioned is not a small list, right? And that speaks to your leadership to having to navigate because I'm sure that tremendously impacted the growth and the way you operated.

SPEAKER_01 24:15

And I think one other important piece is recognizing we can't do all of this alone, and that there are a lot of organizations and other leaders and partners that we can and should work with to accomplish these goals. There's plenty need and there's plenty of work to do, and we're only going to be stronger if we're able to leverage each other's strengths and resources to do that. So I'm very happy that we're part of a number of different partnerships and consortiums to be able to do the work that we do.

SPEAKER_00 24:47

For leaders looking to grow a mission-driven organization, what is the most important shift they need to make to reach their next level?

SPEAKER_01 24:55

I think valuing your team and building that team that you can trust and collaborate with is essential. I cannot imagine accomplishing what we have at Connections without the incredible team that we have to be able to not only implement but help think strategically and bring new ideas and strategies to the organization. So we've been able to learn and elevate what's working well that we've been doing. Connections has been around for 50 years and we have a lot of long-term staff. So being able to hold on to our strengths and learn from that and hold on to the history and what makes us so special, but also bring in new ideas and new staff to always challenge us and help us evolve. But my working in partnership and collaboration is really, I think, a theme throughout my career. And certainly at Connections for Children, I could not accomplish the work that I do without that team.

SPEAKER_00 26:06

And I love that you say team because we do things on our own, but we don't really accomplish anything meaningful and great by ourselves. We just don't.

SPEAKER_01 26:16

It really extends to all of our staff. We have around 60 staff, and I truly believe that we could not move forward without all of them contributing. And I think as a leader, it's important to recognize that every role contributes to our success and to my success, whether that is fundraising or service delivery or IT, we're all part of a system that's working together.

SPEAKER_00 26:48

At She Built It, I'm so grateful for my team. I'm always saying thank you so much for all that you do. We can't do it alone. And it's actually more fun. I agree.

SPEAKER_01 26:57

I'm a very collaborative person. And I also love to see when staff are working out of their comfort zone or developing new skills, doing something that they've never tried before. So I also feel very comfortable in letting other people take the spotlight. I recognize as a leader that is my role and an expectation. And also I look for opportunities to let others step into that role. Sometimes they like it, sometimes it's a little uncomfortable, but they grow into it. So that's been wonderful too in my time here, being able to see some of our staff really evolve and grow in their own leadership and careers.

SPEAKER_00 27:38

Yeah. It's interesting to think of being uncomfortable as growth, but it really is.

SPEAKER_01 27:42

It's always supported. I would always support someone and tell them, I have your back and I'll step in for you, but you you've got this and we have faith in you. We wouldn't put you in this position. And people did that to me as well. I think that's how I had opportunities to grow and to step into roles that I didn't initially envision myself in. It's because someone else gave me that chance or that stepping stone.

SPEAKER_00 28:08

Yeah, we all have to make those leaps at times. And you're on the other side and you think, oh, I was so worried about that, but it wasn't so bad. Look what we were able to accomplish. Yeah. What brings you the most joy in what you're building and in your life today?

SPEAKER_01 28:21

I have so much joy in coming to work and working towards advancing our mission. I feel like I couldn't do the work that I do if I didn't wholeheartedly believe that investing in young children, families, childcare providers is essential for our communities to thrive. I feel so good about what I do. And I love that I'm surrounded by colleagues who feel the same way. I don't think you go into this work or stay in this work if you don't feel that way. So that certainly brings me joy in my professional work and being able to collaborate with so many partners who hold similar values and goals. And also being a parent and seeing my own daughter. I came into the early childhood space when my daughter was 18 months old. And so being able to work in early childhood while I was experiencing that as well was very fulfilling. And now seeing my daughter almost ready to go to college and knowing that those early childhood experiences and the education and opportunities she's had throughout her K through 12 is going to set her up for success. And I want that for all children. So that really energizes me for the work that I do. And I try my hardest to have some boundaries around how much I work and time spent with family. So spending time with my family and friends and travel is also really important to me. So when I'm not in the office or working at connections, that's usually what I'm doing.

SPEAKER_00 30:11

Thank you so much for joining us today and for all the wonderful work that you're doing for Los Angeles and the world. Share with us how and where we can find you.

SPEAKER_01 30:20

So you can find connections for children online on Facebook. It's Connections for Children F-O-R children and Instagram connections for the number four children. And of course, on our website, connections for children four children.org. And of course, you can always call us, and we're happy to help you navigate your childcare options, answer any questions you might have. And if we don't have the answer, we can point you in the direction of someone who can.

SPEAKER_00 30:53

Thank you for joining us today. I'd love to hear from you. Reach out to me at hello at shebuiltit.com on our She Built It website or at She Built It on Social. Thank you to my editor, Rich Draffolino, who always makes us sound good. Until next time, let nothing stop you from experiencing effectively business that you crave.