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This week, The Endowment announced that CEO and President Dan Winslow had tendered his resignation, which the board had accepted. He’d lasted just about nine months, shorter than the tenure of former CEO and President William Buster, who was pushed out in early 2024 after about a year and a half.
The announcement came as quite a surprise to a lot of people, including me.
Now, a lot of us assumed Winslow was going to be a relative short timer. He’s in his late 60s, he’s got family here, and Wilmington is a notoriously lovely place to retire (wish the word hadn’t gotten out, but there’s no putting that genie back in the bottle). And, since he officially started, I’d be tracking some tensions between Winslow, the community, and the board – but, if I’m honest, I thought he had more time.
On Monday, I learned I was wrong about that. (And, on LinkedIn, Winslow said he was heading back to Boston, so I was wrong about the lure of retirement, too.)
There’s a lot to say about Winslow’s departure – both why and how it happened – but that’s not all there is to say. This isn’t just a story about The Endowment’s second CEO resigning in less than two years. It’s also about the board – and the institution – and where this is all going.
It is, at the broadest level, a story that goes back to 2019, when New Hanover County decided to explore the sale of New Hanover Regional Medical Center, a controversial move, resulting in a nearly $2 billion offer from Novant Health. The resulting sale put $350 million in the county’s coffers and created a $1.3 billion community foundation, which promised untold benefits to the community. Even some of those who vehemently opposed the sale voiced high hopes for the New Hanover Community Endowment (despite concerns about governance, transparency, and the exclusive focus on New Hanover County at the expense of poorer, more rural neighboring counties whose residents had helped NHRMC grow increasingly prosperous).
Years later, with two CEOs in the rear view mirror, those hopes are dimmed for some. And it’s not just naysayers who might run out of patience – by 2028 the IRS will require The Endowment to significantly increase its annual giving to at least 5% of its asset value, an estimated $80-85 million or more (currently, its giving is capped at 4%).
Right now, The Endowment lacks a framework of nonprofit partnerships to put out that much money; most nonprofits in New Hanover County lack the capacity to put that much funding to work. Traditionally, a CEO would be the one leading the charge to address that issue – but The Endowment board doesn’t seem to be in a rush to find a new one.
At the same time, others believe The Endowment can get back on track – or find a new direction – and feel there’s still plenty of time to get things right. (After all, barring a pretty extraordinary move, like dissolution, The Endowment is set up to run in perpetuity.)
Ok, more on all that in a bit. But first, let’s get into Winslow’s departure.
Adios, abruptly, again
As with Buster, Winslow’s departure was abrupt and the announcement offered very little detail.
The news came in a press release from Eckel & Vaughan, a high-end Raleigh-based PR firm that has provided communications support for The Endowment on and off since its early days, when it went by New Hanover Community Endowment.
E&V’s release included all the pro formaelements, including a fairly generic sign-off from Winslow:
Leading the Endowment and getting to know the people of New Hanover County has been a true privilege. I’ve made the difficult decision to step away to refocus my time and attention on other priorities. While this wasn't an easy choice, I am proud of the work we’ve done, in partnership with the board, staff, CAC and the strong network of partners in New Hanover County, to introduce the “grants rainbow” and further define the Endowment’s strategic vision. I am confident that this work will continue and will truly transform the county.
While not identical, it certainly rhymed with Buster’s sign-off from 2024:
It has been a privilege to help take this organization from a vision of the board to a functioning organization poised to create change. I have been honored to work alongside this community and team in doing so. I believe the work I led set the foundation for significant change within New Hanover County. I am proud of the path we set and look forward to seeing the endowment fulfill its promise to the community.
Notably, Winslow took credit for the decision to step away while Buster did not. But both dropped key PR terms phrases – ‘it’s been a privilege,’ and ‘I am proud,’ – as well as grand gestures to the transformation or significant change in the community that remains at some point on the horizon.
The release also included the requisite niceties and well-wishes from Board Chair Shannon Winslow (no relation), who oversaw the national search, run by moss+ross (another high-end Raleigh-based firm). It noted that Sophie Dagenais, who was brought on as the vice president of programs and grants about five months ago, would be the interim CEO.
Unlike the announcement of Buster’s resignation, where then-chair Bill Cameron said the board was “totally focused” on finding a new CEO, there was no mention of a search or other efforts to find a full-time replacement for Winslow. And it offered very little room for follow-ups, concluding that, “At this time, no additional information is available beyond what’s included in the release.”
I was admittedly curious why, given that The Endowment has two very capable executive-level communications people – Communication Director Amber Rogerson and Chief Marketing Officer Jodi-Tatiana Charles – the release came from E&V. I asked Rogerson, who told me that, given the “sensitivity” of the situation, the board felt comfortable going with a PR firm.
To me, all this indicated there was little time to plan.
I’ve heard rumors that Winslow’s office was cleared out just a few days, possibly the day before, the announcement. I’ve also heard that Dagenais – who is now ostensibly running day-to-day operations – is currently on vacation in Europe. If there was no acrimony, crisis, or other expedient need for Winslow and The Endowment to part company in short order, it seems like they could have taken a few days to allow a smoother transition, wait for Dagenais to get stateside, let Rogerson or Charles craft a statement and field some questions, or even make someone from the board available for a brief interview (leaning, of course, heavily into their confidence in Dagenais and assurances that the good work would continue).
Winslow, I’m guessing, had been instructed or incentivized not to talk to the press, and while I suspect the folks from Port City Daily, WECT, and the Wilmington Business Journal worked their phones as much as I did, nothing on-the-record emerged from staff or the board (the media discipline is objectively impressive, even if it's infuriating for a journalist). One notable exception: board member Woody White posted emphatically on X about his preferences for the next CEO (put a pin in that, for a minute).
And look, most of you have been around the block enough times to recognize when a PR firm is putting a good spin on things. (If you haven’t, it looks like this.) And, while it’s important to note that messy is not the same as malicious, the optics here are not great, and if The Endowment does decide it wants to pursue another national search, it could be tougher because of that.
Quick. Also, not quick enough.
So, why was Winslow out, and so quickly?
I can’t tell you for sure; I haven’t heard of any one single inciting incident. But I’ve scrounged up a few clues.
I’ve heard from many non-profits that Winslow was charming and engaging, but it seems he might have been too encouraging. I hadn’t exactly heard of him overpromising – and I’ve noted his use of cautious language when he’s around potential grantees – but I have heard that he’d at times suggested nonprofits pursue bolder ideas and more significant asks. I'm not sure this sat well with some board members.
Winslow’s personality – which, love it or loathe it, is certainly big – also seemed to clash with the desire of some board members to stay out of the news and under the radar. Experts on philanthropy who’ve shared their insights with me over the last few years have often suggested that foundations ought to keep a low profile, that the real focus should be on the issues and the nonprofits addressing them.
I’ve heard some were rankled by a Request for Proposals that The Endowment put out for studies on organization, compensation, and benefits, including for Winslow. It’s not uncommon for foundations to do this kind of study, experts tell me, especially for young and growing organizations. But it seems Winslow may have been angling for a raise, less than a year into the job. Notably, Buster was paid handsomely – over $400,000, according to the 2023 IRS filing – and I suspect future filings will confirm Winslow made less than that.
It also seems that Winslow may himself have had commitment issues. According to voting and property records, he was renting a riverfront apartment, and never purchased a home (as Buster did), something he implied he would do when he came down from Boston. While you could also attribute this to Wilmington’s bonkers real estate market, I think some read it as hesitation.
All of this seemed to be, well, not exactly what The Endowment wanted. I know it’s a cliche, and often a PR dodge, to say someone ‘wasn’t a good fit,’ but I think at some level, that does seem to be the case here, based on the admittedly thin amount of information that’s out there about it.
Winslow’s bombastic side is a matter of public record, as we reported when he was hired, but he was picked for his skill in building teams, adapting to new environments, and – as I’ve heard it put – “getting shit done.” Unlike Buster, Winslow had zero experience running a major grant-making organization (and his retort, that he had experience applying for grants, wasn't wildly reassuring). But he brought a ‘how hard can it be’ attitude that, at least to some, was convincing. Winslow told me he was a “quick study,” but also that he didn’t need to have philanthropic experience to get out of the gate, as long as he could hire a team of people who did, and manage them efficiently.
I think it’s fair to say some board members saw him as a necessary pivot from Buster, who was good with big-picture ideas but seemed to struggle with convening non-profits and building up their capacity to the point where they could execute on some of those grand plans. It’s worth noting that Buster didn’t get the resources – namely, the staff or budget – that Winslow had, as he was taking the reins of an essentially brand-new organization that had barely gone from an idea on paper to a real-world entity. But, all that said, you could understand why The Endowment might want to focus on results over aspirations, at least as they were trying to get more established.
To me, though, it seemed Winslow ultimately made bigger promises than Buster did, repeatedly saying The Endowment would deliver “transformational change” – things like rebuilding the Black middle class, supporting world-class education, and solving a host of other community issues. But those things take time. The multi-million-dollar nursing pipeline grant, for example, addresses a dire issue at NHRMC, and puts hundreds of students on track for a good career, but it will take years to really make an impact. Changing the socioeconomic landscape, likewise, won’t be an overnight issue.
I can’t speak for the board, but certainly people in the community I’ve spoken to were getting frustrated with the dissonance between Winslow’s grand promises and what was actually happening at The Endowment – which was over $100 million in grants going into the community that weren’t quite world-changing but important just the same.
I should probably have said this more often, but there’s a lot of good that The Endowment has done. I take some responsibility for not focusing on that enough, but I think a more modest sales pitch from Winslow also would have helped. Winslow was a quick study, I give him some credit for that, but I don’t know if he got the hang of New Hanover County’s socio-political dynamics quickly enough.
At the end of the day, there don’t seem to be any fire alarms going off at The Endowment over Winslow’s departure, and the board seems confident that Dagenais is more than competent to wrap up the $15-20 million in grants that are slated for the remainder of this calendar year (based on what Winslow and Dagenais said during the spring meeting). And Rogerson told me The Endowment’s plans to build out what will effectively be an R&D wing are still ongoing (the idea is to put out requests for studies that The Endowment will publish and then convert into grant opportunities: currently, there’s an RFP out for ‘recreational opportunities’ – not the first place some advocates would like The Endowment to look, admittedly, but at least the wheels appear to still be turning).
That’s prompted the question: what, then, was Winslow doing? It’s entirely possible that Winslow’s abrupt departure is not a crisis. But if the board is untroubled by Winslow’s departure, it implies that despite his (I’m sure) significant salary and high profile, he was not the lynchpin for the operation. That suggests, to me and others I’ve spoken to, that the board is probably still involved in a more granular way than they’d like to be.
Eventually, as past board chairs have told me, the idea is for the 13-member board to set strategy and let the CEO execute it. Oversight, not operation. To get there, they’ll need a CEO who succeeds where Buster and Winslow did not.
What now?
So, eventually, there will be a new CEO — although finding someone competent, tuned in to what’s going on, able to work with the board and the community, and willing to step into the breach, well, that will be daunting, to say the least.
It could be Dagenais, who is currently getting a chance to earn a battlefield promotion. Or there could be another nationwide search, although as I’ve said elsewhere, philanthropy is a small world and some candidates might warily be asking themselves why they’d follow in the footsteps of two other hastily departed CEOs (others, though, might relish the challenge).
But The Endowment could also, as board member Woody White posted on X, hire locally. While other board members kept quiet, White forcefully argued that, if he had anything to say about it, there would be no more nationwide CEO searches.
“No one in this nation - not the best philanthropist, the most acclaimed ‘community organizer’ or the most motivated empathetic individual - could possibly know what our local needs are better than what we know ourselves,” White wrote, adding that “This is a point that many of us on the board have been making for quite some time.”
White, tweeting late in the evening, was quick to amend his post, noting that he was not TWI (Tweeting While Impaired, certainly a liability for some folks), but was sharing what he acknowledged to be a potentially controversial take after due consideration. And beyond the choice of CEO, White also suggested The Endowment needed to focus on its original purpose, as laid out in the NHRMC sale agreement between Novant and the county, which was to align with the county’s strategic plan.
White’s posts were shared approvingly by a host of local Republican politicians, including State Senator Michael Lee, Wilmington Councilman Luke Waddell, and Commissioner Dane Scalise (who doesn’t have a direct say over the issue, but will play a strong role in appointing the county’s five seats on the Endowment board).
I've heard from plenty of more conservative folks who feel like White is talking some much-needed sense, and also those on the left who were quick to suggest some kind of grand cabal conspiracy.
But I have to ask: what exactly is the evil plan? Maybe I’ll end up looking foolish for that. But I’ve given it a lot of thought.
I don’t think, on the face of it, a local hire is necessarily a wild idea. There were, after all, locals who threw their hats in the ring in the national search last year. And most organizations go through periods when, for a host of reasons, they’ve promoted from within or hired locally (Winslow actually said he made a point of hiring locally when possible). And while some experts have suggested philanthropic experience is a must, and I’m inclined to agree it’s important, certainly understanding our region and the key players would be beneficial, too.
Some have suggested there would be cronyism or ideology involved in a local hire, and those are fair concerns (and we’ll obviously vet whoever is eventually hired). But it’s worth remembering that White is influential, but he’s also one of thirteen board members. There’s likely to be some robust debate – both over whether to hire locally and, if that’s the will of the board, who to hire.
Moreover, if the board has decided that the CEO’s job is really to execute their vision, and that vision is guided by the county’s strategic plan, then it’s the board and the vision – and the plan – people should pay the most attention to.
I’m not saying people shouldn’t be skeptical, but – especially if you think The Endowment has lacked focus and direction – there are worse fates than a return to its founding documents.
Consider the ‘focus areas’ included in the sale agreement (pages 162-163, if you want to peruse for yourself). It’s a long list, and it was intended to be an ‘illustration’ of possible ways The Endowment could serve the public, but there are plenty of ideas here that many people would enthusiastically support.
***
A. Public Primary, Secondary and Post-Secondary Education. The following are illustrations of possible initiatives:
1) High-quality universal pre-kindergarten with wrap-around services;
2) Comprehensive, no-cost broadband connectivity countywide;
3) Comprehensive access to modern technology for all learners;
4) Local Teacher Fellows program for traditional and charter school graduates committed to returning to local public schools;
5) Access to scholarships for post-secondary education attainment; and
6) School facilities designed for mid-21st Century education delivery.
B. Health and Social Equity. The following are illustrations of possible Initiatives:
1) Eradicate food deserts across the county;
2) Expand access to high-quality, fair-cost physical and mental health clinics for county residents;
3) Funding support to eliminate disparities in health outcomes focused initially on diabetes and obesity;
4) On-demand, cost-effective transit system for dependent and choice riders; and
5) Funding for new senior resource centers and other support for senior citizens based on the county’s strategic master plan for aging adults.
C. Community Development, The following are illustrations of possible initiatives:
1) Workforce housing trust fund;
2) Small business micro-loan program-,
3) Minority and Women Owned Business support programs; and
4) Open space and public water access preservation.
D. Community Safety The following are illustrations of possible initiatives:
1) Next generation 911 services developed and deployed;
3) Support and resources for community-led restorative justice programs;
4) Modern development and training of law enforcement, to include cultural competency and implicit bias; and
5) Comprehensive flood, storm surge and wind mitigation investments,
***
If The Endowment were to simply work through this list, it would be monumental.
And, I know there are some who are concerned that the conservative dream is for The Endowment to essentially take on everything the county currently does beyond the bare minimum (except for the Sheriff’s office, which technically only requires two deputies), allowing the county to lower its tax rate as much as possible. I’ve heard arguments that the county has a moral or ethical obligation to provide those services that go above and beyond the “core services.” But at the same time, I’ve heard people say it’s a no-brainer for The Endowment to fill that role. “That’s what it was created for,” is a common refrain.
And I have to admit, the arguments about social safety nets and other government programs look a little different in New Hanover County, with a $1.6-billion foundation, than they do elsewhere.
Whatever you think about that, The Endowment will soon face a critical situation, where it will be required to put out over $80 million a year. And, again, there aren’t a lot of nonprofits in town capable of handling that kind of funding (although there are some, and I hope they do get funding). It’s an almost insane proposition to find ways to spend that much money year after year.
At least in the near term, one way to do this is to take on some of what local government has been doing. The Endowment’s founding documents prohibit it from “substituting” for government funding, but allow it to “supplement” the government.
There are a lot of creative ways you could approach that: they could, for example, work with the city and county to end chronic homelessness, build a new library and senior center, stand up a small business loan program and a housing trust fund, buy a park, and update all the school computers. All that would probably exhaust only a year or two of funding. Year three? Pick up universal pre-K or build child-care facilities. Year four? Overhaul school facilities. With $80 million or more a year, you could do all this and still fund local non-profits with millions in annual grants.
As I said, there are worse outcomes.
This is, again, a story that goes back to 2019, when the county started publicly considering selling the hospital (though the idea had been around for a while). While I ultimately understood the county’s rationale for the sale, I was critical of the process, at the time, including how The Endowment was created. Were it up to me, I might suggest dissolving the current organization and reforming it, excluding Novant from the appointment process, and requiring public meetings and other transparency measures (that’s no disrespect to current and past board members, who I know care about the community and who wanted to honor the intent of the founding documents, which are barely five years old).
But it’s not up to me, and my personal take isn’t as important as The Endowment that we do have, and what it can do. If there is a consensus forming around a local hire, and a return to the county’s strategic plan as the North Star, that’s probably where things will go.
There are plenty of pitfalls on that course, and lots to keep an eye on, but there’s also potential for a lot of good work – and real, meaningful change.
