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In Conversation With: Michelle Wamsley, Chief Advancement Officer at Habitat for Humanity of Greater Charlottesville.

As an executive search firm specializing in the nonprofit and social impact space, we get to connect a diverse group of purpose and mission-driven leadership candidates with fulfilling, impactful roles at some of North America’s top organizations.

We recently reconnected with Michelle Wamsley who we placed at Habitat for Humanity of Greater Charlottesville in 2022. Now their Chief Advancement Officer, Michelle shared insights into her role and how the organization is working to achieve its mission, her experience working with DRiWaterstone, and some great advice for other candidates looking to transition into a leadership role with a nonprofit organization.

DRiWaterstone (DRiW): Talk about Habitat for Humanity of Greater Charlottesville and your role there.

Michelle Wamsley (MW): We are a mid-sized affiliate serving a mid-sized market. In the last 30 years, we have built more than 350 homes and created more than $100 million in equity for our local families, and that’s generational wealth building here. And we are doing some innovative, national-model projects here, including the redevelopment of a 350-unit trailer park on 123 acres – taking a mobile home community and turning it into an 1,100-unit mixed income community.

I’m the Chief Advancement Officer here at Habitat, which means that I wear a lot of hats! I head up our private fundraising (from individuals and from organizations) as well as oversee our government grants. I also oversee marketing and communications, volunteer engagement and management, office administration, human resources, and regional housing.

DRiW: What is one tip that you would give to other candidates who want to take that next step or to move into a position like yours?

MW:  Especially if you’re doing something like changing fields or pivoting a bit, I would say to really give yourself some time, and to be humble. You might know a lot about where you’re coming from, but the nonprofit sector is really diverse and can be vastly more complex than people think it is.

DRiW: Talk about your experience working with DRiWaterstone.

MW:  It was great. I had known my recruiter previously, in a different capacity. He and I had worked at a university together and had a conversation a couple of years prior to my reaching out about this position when I happened to see it. It was a wonderful experience – he was so knowledgeable and helpful and really had a good feel for the organization and exactly what they were looking for.

DRiW: How did the team at DRiWaterstone support you during the recruitment process?

MW:  It was everything from scheduling to making sure I had background on the people I was going to meet with at Habitat (which was phenomenally helpful), to understanding exactly what they were looking for, where the challenges were, where the opportunities were, how they were hoping to grow, and what they were hoping for in this role. [DRiWaterstone] really helped me understand how I might be a fit, and how this role also might fit into my long-term career plans. So, it was very helpful for me to be able to work with a true partner who could help me feel engaged in the process and knowledgeable every step of the way.

DRiW: What is something you didn’t know about executive search firms before working with DRiWaterstone?

MW:  Because I’d been in higher education for years, I’d worked with search firms for many years – many larger search firms though; I’d never worked with a boutique, smaller search firm that was focused on nonprofits. For me, that personal touch was really different as a candidate. It was an entirely different experience in terms of what I had experienced with larger firms. It was just very personalized, it was attentive, it was kind, it was always making sure that I was in the loop about exactly what stage we were in. As a candidate who was busy with another existing role, that was a real gift to be able to have a partner like that.

DRiW: What advice do you have for other candidates when it comes to working with an executive search firm?

MW:  Be open and honest and transparent in having conversations. This person, they want to do the best they can for their client, and they also want to work with you. And that can also become a long-term relationship over time. So, I’d say stay open, be honest and transparent about your needs, and be thoughtful and willing to listen to what they might say about why this might be a good fit – or how perhaps it’s not, but maybe they have other opportunities.

I would say just to make it a real dialogue and that’s how it’s going to be beneficial to both of you.

DRiW: What’s next for Habitat for Humanity of Greater Charlottesville?

MW:  We’re going to continue our work in Southwood, the transformation and redevelopment of our mobile home park into our mixed income community. We’re going to continue to build in the City of Charlottesville. We have three rehabs right now and a couple here in the city that will test out some of the new zoning ordinances here in the City of Charlottesville to increase density, which we’re very excited about. And we’re going to continue our critical home repair in the local counties of Greene and Louisa, which are really helping to keep a lot of elderly folks in their family homes as they age in place. We’re excited about all of that.

And then just continuing to serve our community and to continue to serve as a model, where we can, for other Habitats across the nation as we seek to preserve and expand the affordable housing stock.



At DRiWaterstonewe have the pleasure to work with some of the best purpose and mission-driven clients and candidates in the nonprofit and social impact space. To learn more about how we can help you build your high-performance teams and drive growth, email us – we’d love to talk! 

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According to a recent article in the Chronicle of Philanthropy, nonprofit organizations across the U.S. are facing a major challenge when it comes to hiring leaders into CFO roles. Given the critical nature of the role, finding a candidate with the right mix of skill and connection to mission is key – and a skills shortage presents a challenge that many organizations in this space may not be able to solve on their own.

At DRiWaterstone, we’re experts in helping organizations recruit purpose and mission-driven leaders for tough-to-fill roles – whether because of talent shortages or unique skills and requirements. When it comes to finding financially savvy leaders who can manage the fiscal challenges of nonprofits, foundations, associations and other social impact organizations, our executive search professionals have three tips:

  • Think outside the (nonprofit) box
    It would be easy to think that because you’re looking for top candidates who understand the complexities of managing the financial wellbeing of a nonprofit, foundation, or association, that you need to look for candidates with extensive experience in the industry. While this may be true in some cases, for most roles, it’s not! In fact, looking outside your field or industry may result in candidates who have skills and attributes that you didn’t know you needed. Take the time at the beginning of your search to really understand what’s a “must have” and what’s a “nice to have”, and then test your assumptions by looking at traditional candidates as well as few outside the box candidates. Don’t be afraid to re-visit your candidate requirements if needed!
  • Don’t ignore up-and-comers
    Many organizations opt for tried-and-true leaders when searching for senior-level roles – those with a track record of success at the senior level. But there’s a lot to be said for exploring next generation talent, especially when faced with a smaller or more challenging talent pool. When it comes to recruiting CFO talent, why not consider a rising star? Recruiting someone who is doing great things at the vice president or executive vice president level and who is ready to take the next step in their career may be the right fit for your organization – they will bring a fresh perspective, may be more open to changing companies/industries for the learning opportunity, and may better align to your budget than someone who’s already in a C-suite role.

For more than 20 years, the executive search experts at DRiWaterstone have been helping nonprofit and social impact organizations across the United States recruit leaders who move their mission and performance forward. Connect with us to find out how we can help you succeed with your next CFO search.

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