Community Leadership Spotlight: Halley Crumb

“The Art of Leadership is to create a team whose mission is to support humanity with ❤️. “ 

As a part of our Community Leadership Spotlight Series (CLS), we spoke to Halley Crumb, founder and CEO of Retraining the Village. In this powerful conversation, Halley shares what drives her, the lessons learned in building grassroots solutions, and her bold vision for a future where dignity and opportunity are for everyone. 

About Halley Crumb and Retraining the Village 

Halley Crumb’s journey has been shaped by resilience, determination, and a deep commitment to serving others. From an early age, Halley demonstrated an entrepreneurial spirit and a passion for community impact. Over the years, Halley has navigated personal and professional challenges that built not only character but also a strong sense of purpose. Those experiences became the foundation for leadership in nonprofit service, advocacy, and transitional housing programs—particularly for vulnerable populations such as veterans, formerly incarcerated individuals, and people at risk of homelessness. 

Today, Halley is a driving force behind initiatives that make a measurable difference in people’s lives. As CEO and Founder of Retraining the Village, Halley leads a team dedicated to providing housing, supportive services, and pathways to self-sufficiency. Halley is recognized for developing policies and programs that balance compassion with accountability and for building strong partnerships with county agencies, donors, and community stakeholders. Whether designing business plans for Medi-Cal-funded services or creating frameworks for substance abuse treatment and reentry, Halley’s work reflects a steadfast commitment to uplifting underserved communities. 

Looking ahead, Halley envisions expanding Retraining the Village into a statewide model for transitional and permanent supportive housing. The goal is to integrate evidence-based mental health and substance use treatment, scalable workforce development programs, and innovative funding partnerships. Halley is determined to secure sustainable resources and advocate for systemic policy changes that create equitable opportunities for all. The future holds new chapters of impact, including the potential to influence legislation, mentor emerging nonprofit leaders, and continue transforming lives across California and beyond. 

The Journey 

CLASS: We are so happy to sit down today with Halley Crumb, the founder and CEO of Retraining the Village, the nonprofit organization that works to help veterans, the homeless, and formerly incarcerated individuals to attain permanent housing. Halley, it is such a pleasure to speak with you today. Welcome to The CLASS Consulting Group Spotlight series. 

Halley: Thank you for having me. It's just a joy to meet you. Thank you for the opportunity to be “Spotlighted”!   

CLASS: Your journey into nonprofit leadership is so inspiring. Which pivotal moments in your life shaped your path to finding and leading Retraining the Village? 

Halley: It was a few things, starting from my childhood. My dad was heavily incarcerated multiple times, and a lot of my uncles went to prison too.  

I was working at the VA Hospital in San Francisco as a laboratory technician and phlebotomist. I saw firsthand how veterans were treated. They’d be in my office waiting for their blood draw. 

Back then, in 2009, veterans would often have their appointments canceled, even though they were physically on campus. I’d see them waiting in long lines and immediately call the clinic - “Hey, they’re here. Don’t cancel—they came all the way from Lake County.” That small action often meant that that veteran got to see their provider that same day. 

Since then, things have changed drastically. Now veterans can do a video call or are seen in-office with better coordination—things changed to where there were no more cancellations without notification. That was a pivotal moment for me.  I was just becoming clean and sober for about four or five years myself. There was a big call to clean up the Tenderloin, and all the veterans had to come back to their base. I’d say, “Hey, you’re six months clean”, “You’re four months clean,” and they’d look at me like, “How do you know?” I’d say, “Because I’m proud of you.” So, I inspired them to keep going. 

Our conversations would often go beyond blood draws. I’d ask, “Where do you live?” They’d say, “Downtown in the Tenderloin,” and I’d ask, “Do you want to stay there?”—simple conversations while drawing their blood.  I got the Special Contribution Award and the Good News Travels Fast Award, just for taking the extra step. Just being concerned about how they were doing. 

So to answer your question: I love what I do. It’s not work for me—it’s a calling. I’ve been doing this for over 13 years, all self-taught. I didn’t go to school for it, but I was blessed to land a house in East Palo Alto—on the corner of Alberni and Menalto, which at one time had the highest murder rate in 1987. That one house was the nexus for the entire neighborhood. The home came from Mr. Edward E. Campbell Sr., a pioneer and advocate for the homeless. I asked how much—he said $500. Can you believe that? 

Around the same time, things at the VA took a turn. A supervisor made a disrespectful comment about my hair, and not long after, they offered to retire me. I was 48, suddenly retired, with a check and a lot of legal drama behind me. I asked myself, "Now what?" 

That’s when Mr. Campbell came with the house, and from there, Retraining the Village was born. Thirteen years later, we're still here. It all came together in a way that I truly believe was divine. I didn’t know what to do at the time—but I knew I had to serve people who were less fortunate than me. 

CLASS: So, all these different factors in your life lined up and came together - the good work that you were doing with the veterans at the hospital, this toxic boss, and the gift of this house in East Palo Alto. All the stars aligned. 

Halley: Yes, they did exactly. So, I used my retirement money to beautify the home and put in a new walkway. Fixed the doors—some were even on backwards—and replaced what was chaos with care. Crows were in the front yard, and eventually it bloomed—literally—from crows to a rose. 

Father Goody came and blessed the home, and I truly believe that everyone who’s walked through that door has been blessed. I’ve served thousands of people in the community through housing and outreach to the homeless, giving them an opportunity to rest. I don’t take away from the shelters, but what I provided was a different type of shelter. It was a shelter with a stove and a TV and a kitchen and a bathroom and laundry facilities you could use at your own will with no time limits.   

That’s how it started. We changed the face and function of shelter living—and it worked. 

CLASS: What has been the most unexpected leadership challenge that you have faced in your nonprofit journey and how did you address it to continue advancing the mission of Retraining the Village? 

Halley: One of the most unexpected challenges was realizing that not everyone was ready for change. The funders, the county - they weren’t ready for a person who knew what was going to happen before it happened. I had seen the change coming a couple of years prior because we went through gentrification when Facebook came into East Palo Alto. 

While I was getting my homeless people ready to pay $700 a month in rent, suddenly, it jumped to $1,700 for a studio. I had to adapt to what Facebook was doing – you hire somebody, have them live in the home, feed them in the home, and/or they’re getting a job, but they can’t use all their money because they have to save money. As part of my program, you have to be financially literate in order to move to the next step because you have to pay your bills first. So that prolongs some people’s stay. 

I was born and raised in East Palo Alto, and watched all the changes in the atmosphere, the gentrification. At the same time, I was changing too. I didn’t see myself as a leader at first. I thought, "I’m just doing what needs to be done." 

But leadership isn’t always about knowing exactly what to do. Sometimes, it’s just doing. And I struggled with the idea of asking for help. Growing up, asking for money felt like weakness, or it had strings attached. I didn’t know how to ask. So I wrote it down. I applied for grants. Lockheed Martin was my first one that was $25,000. Then came Safeway with $1,000 for groceries. So, what I would say was the ask, and knowing that I was becoming a leader. I was becoming a change maker, unconsciously.   

CLASS: So it sounds like you really surprised yourself with what you were capable of, right? 

Halley: Yes, I would get up at 4:00 AM and Google the question "How do I do this?" I’d study it, learn it, figure it out. Being self-taught takes time. I didn’t know who to ask. Coming from the hood, I didn’t grow up meeting people like you—I didn’t even know people like you existed. All I knew was that what was right in front of me was to help people help themselves. Now, 13 or 14 years later, yes—I know I’m a leader. I lead Retraining the Village. I don’t have it all figured out, but it's taken all that time to even ask for help. 

CLASS:  If you could give one piece of advice to someone who's stepping into nonprofit leadership today, what would it be? 

Halley: Just do it. Educate yourself. Understand the laws. Understand your purpose. Write it down. Inadvertently, I became a consultant. I have helped ten people start their nonprofits. Ten - and four of them are successful because they stayed right with me. I feel they're all successful because they just did it, and not from a place of ”where is the money?” but rather from a place of ”how can I help?” How can I support the youth? How can I support the adults? How can I support the people who help out with substance abuse? They just wanted to do all different types of things. And since I started my paperwork on my own, I helped them out with their applications, and they’re still in existence today. So, what I would say is, make sure you know who, what, when, where, why and how. Get to the basics of knowing what you're looking at. Get your demographics of the needs. Get the population of who you want to serve - male, female, both, pets...  You know, just really educate yourself in what you really have a passion to do. And just do it. 

CLASS: That's amazing that you have helped so many other nonprofits to be successful. 

Halley: Each one teach one. That's why we're Retraining the Village. It's a village. It's a collection of people. I've never seen a village with just one person in it.  It's beautiful. 

The Key Initiatives 

CLASS: If you could please highlight a current or recent initiative that you're especially proud of, and what outcomes it is driving. 

Halley: The initiative is homelessness. Because under all of the services, the main commonality is homelessness. Whether you're a veteran at risk of homelessness, a re-entry person who's just done 30 or 40 years, even if you're a pet - I do shelter with pets – all of these are at risk of homelessness.  I have so many success stories, but I'll let you know about the recent one. Rich Lee from Daly City and I, we did a podcast recently with this young man who came from Visalia in the Central Valley. And people say, oh, they’re in California; they do what we do. No, no, no. In Silicon Valley we have the absolute best systems and collaborations to help people throughout many, many states. The services we have, the connections we have together, the culture we have together, and the diversity we have together. People always say it’s expensive, but it’s the best expensive place in the world! 

So this gentleman, who I talked with when he was in prison as part of the pre and post incarceration BJA (Bureau of Justice Assistance) Second Chance Act, he said, “Well, I'm just going to go back to the Central Valley.” And I was like, “No you’re not. Let’s send you to school. If you could go to school for free, what would you do?” He said “I want to go into HVAC”.  I said “OK. Let’s make that happen. Then what else do you want to do?” He said “Well, I want to give back.” So, he went to school. He worked for me as an outreach tech and he went to school for job training. He just graduated in the Class of 2025. I highlight him because he landed a job within two weeks after his training and he went from what I could pay, which is a little bit of nothing, to $38.00 an hour.   

CLASS: Congratulations to him. 

Halley: It’s just miracles that happen every single day. 

CLASS: How does Retraining the Village approach systemic issues like homelessness, incarceration and joblessness differently from other models? 

Halley:  We are the village. Each one takes care of each one. We ensure that there are checks and balances to every house, and here in East Palo Alto there are seven. Within their community it's mandatory for them to sit down and get to know the people who are there. It's a village, and we love this community, and each and every community that we go into will be the same model. Each one teach one. They have freedom now, freedom from the streets, from almost dying at night, laying in the streets of San Francisco or bumping into somebody that can hurt you. It's dangerous out there. Every aspect of homelessness is dangerous.   

CLASS: Is there a story of transformation - an individual or community that continues to inspire your team?  

Halley: The community of East Palo Alto has changed a lot. We just had our Juneteenth and it was wonderful seeing everyone there, no violence. Just a whole bunch of love and happiness to see each other. It was beautiful. East Palo Alto is different than any other city. It’s always been a village. We all look after each other no matter what you look like.  

CLASS: What has been your proudest moment as a nonprofit leader so far?  

Halley: The expansion of Retraining the Village. I didn’t know if it would get past five years, but I knew that once it did, it was going to be a force to be reckoned with. So, I’m proud of Retraining the Village. I'm proud that each person that comes through those doors recognizes that they have been chosen in a special way by a higher power. And I'm really proud of the way the neighborhood receives them – the support of the community and everybody involved in helping another human being reach their full potential - potential they didn't even know they had.   

CLASS:  t's incredible that it's been 13 years since you started Retraining the Village, and you've gone from one house to now seven. You've helped thousands of men to get back on their feet and find permanent housing. That’s a wonderful success story. Where do you see Retraining the Village in the next three to five years? Are there specific dreams that you're working towards? 

Halley: In the next three to five years, I want to help more people who have mental health issues snap back, to help the elderly who are in need, because the homeless population is getting older. To put systems in place where it's a breeze to get through like I have with the veterans. We need more of that kind of system where they can come in and detox, and then after they detox, they get into permanent housing, and from permanent housing, their HUD voucher is right there. So, I get to be the place where you can slow down a little bit, get accustomed to coming home, get accustomed to having some place where somebody wants you to be there, without any assumptions and a whole bunch of forgiveness. And then we can figure it out together.    Right now, we're becoming  Medi-Cal licensed. We're going to be in every city in California for reentry. We will be going into the prison system at least once every six months to let them know that housing and support is available, and here are the rules. 

CLASS: Wow, that's exciting. This is a huge next step for you, right? 

Halley: Yes. So the next city is Bakersfield, and Bakersfield really needs this recipe. 

The Leadership Challenge 

CLASS: Are there certain kinds of support, resources or partnerships that would help you to scale your impact or strengthen your operations? 

 Halley: Oh my God. From fundraising to accounting to attorneys to resources. I don't have any. I have so many hats to wear, and now at 60 years old, it's time to take off some of these hats. The cost of living here is high, so to get a person here to help me, I would have to close a few doors. What would help me is volunteers who are already doing the job, so it's a no brainer for them. I do need support on the administration side. I do need support in the functionality. Putting systems in place that work.  CLASS: If you could wave a magic wand and instantly solve one challenge your clients face, what would that be and why? 

 Halley: Their self-reflection. The way they think of themselves. I would love for them to see what I see in them and what God sees in them. I would love for them to see that. Even if it's for a split second, I want to say this is what I see, and this is what God sees for your life. I get the opportunity to see it before they do. And then we do an individual case plan, and I show them if you go here on that dot and then you get to that dot and then you get to that dot, you're going to be successful. And I do it every single time. That's why my baby is at work right now, making $38.00 an hour. He hit all the marks.  CLASS: Final question. What legacy do you hope to leave not just as a leader, but as someone who started this endeavor, Retraining the Village? 

 Halley: I would like to leave a Sasquatch size imprint on how each person can help each other. Human kindness works, if you know how to work it, to give faster than receiving, to see a need and fulfill it, instantly, no questions asked and no admiration or nothing needed behind it. Random acts of kindness go a long way. So I would like to leave a Sasquatch size imprint in my legacy, something huge, and that is just having the heart to do it. Just doing it. Just move forward – touch the back of your head - that's over. Touch tip your nose - move forward. That's it. 

CLASS: I think that's beautiful and that's a great place to end. Thank you so much, Halley, for sitting down with us. This has been such an inspiring conversation.  

Halley: Thank you. 

About The CLASS Consulting Group

The CLASS Consulting Group is a trusted advisor to the boards of directors and senior leadership of the West Coast nonprofit organizations. It is a boutique management consulting firm headquartered in the San Francisco Bay Area that provides consulting services to senior management and board of directors of nonprofit organizations and offers community leadership opportunities to professionals.   

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