James Sherry’s career has taken him from his Australian hometown of Melbourne, a city of more than 5 million people, to a tiny Australian island with only a few thousand inhabitants, to short stints in China and Guatemala, to New York City and, now, to Cincinnati and Northern Kentucky, where he serves as CEO of Holly Hill Child & Family Solutions.
(Photo by Helen Adams for Movers & Makers 2025)
Though the work has varied and the places have been vastly different, Sherry’s attitude has been consistent.
“I’ve loved everywhere I’ve been and everything I’ve done,” he said.
“What I’ve realized is there are amazing people everywhere, and every place on the planet has its really unique charms,” he added. “So if you can just appreciate where you are, you always love it.”
That mindset has served him well.
“It means everything is always fantastic,” he said. “Sometimes things can be pretty challenging, but I also find that if you put your head down and focus on doing what’s right, then the chips start to fall your way, and you get those wins for the people you’re working for.”
A matter of chemistry
Sherry speculates he “might be blessed with just really great brain chemistry” that contributes to his positivity. But had he been better at chemistry as an academic subject, his career might have looked quite different. From a young age, he wanted to be an environmental scientist. When he started pursuing an undergraduate degree in that discipline, however, he determined chemistry wasn’t his strong suit.
His research at the end of his undergraduate program focused on local government land use policy. That work shifted his interest from ecological science to social science and led him to start his career in government policy, strategy and research, first in the private sector and then in local government.
After earning his MBA in 2012, Sherry went to work for Queensland Health, the largest health care provider in the Australian state for which it’s named. That took him to tiny Thursday Island (Waiben in the local Kawrareg dialect), where he ran nonclinical health services for the region. Shortly thereafter, he moved to the head office in Brisbane, where he held a series of roles culminating in chief risk officer and director governance.
While there, he took a summer-long sabbatical to attend a “senior executives in state and local government” program at Harvard Kennedy School. He’d heard about it through one of the many boards he served on early in his career, which provided an “unbelievable opportunity to have insight into how organizations, especially nonprofits, run,” he said.
His first board was significant; he’s come to realize it “almost set a template” for his career path. Before Sherry was born, his grandfather started a nonprofit age-care facility. A builder by trade, he got federal grants, a donation of land from the local government, and fundraised through church and his Rotary Club to fill a need he saw in his community.
“That’s kind of been a theme (for me), seeing a problem and doing something about it,” Sherry said. “I didn’t realize it at the time, but it has set the tone for what I’ve done.”
As it turned out, the Harvard program also set something in motion – Sherry’s interest in working in the United States. In 2018, he moved to New York to work in developmental disabilities. After a short stint as vice president of WellLife Network, he became CEO of New York Families for Autistic Children.
From NYC to NKY
So how did he find himself in Northern Kentucky?
“I do what’s right and what’s in front of me,” he said.
When a national search for the new CEO of Holly Hill came across his radar, he visited its locations in Highland Heights and California, Kentucky to interview. Meeting the girls in the organization’s residential program convinced him it was the right move.
“Having some insight into the work we do with them was like, ‘Alright, I’ve been involved in a lot of really great things; this can be another one of those,’ ” he said.
He also appreciated that during his short visit, the board highlighted both the strengths and challenges at Holly Hill, which focuses on mental and behavioral health services for children and families. “The whole process indicated to me that no matter what the challenges were, together we were going to be able to do some great work,” he said.
The board got the same impression from Sherry.
“He really had a ‘can-do’ attitude, that there is no problem too big for him to figure out,” said M. Erin Wilkins, an attorney who was board chair during the hiring process and has since worked closely with Sherry as a board member. “What struck me in his interviewing process, and also continues to strike me today, is really how open and curious James is about everybody he meets … He was somebody who could talk to anybody.”
Sherry joined Holly Hill in January 2022 in the midst of what he describes as a “burgeoning mental health crisis” and significant changes at the federal level. The organization, which has a budget of $4 million, offers a range of services: residential treatment, supervised visitation, day treatment, therapy services and targeted case management.
Holly Hill’s residential program, serving girls in the state foster care system, was already working with victims of human trafficking. Sherry saw “such an extreme need to support these girls” that Holly Hill adapted its programming and is now a year and a half into a pilot with the state to focus on that subpopulation and on high-acuity youth (young people who require intensive support) in the child welfare system. As part of that program, Holly Hill’s reimbursement rates increased – for the first time in years, Wilkins said.
The program currently has a capacity of 12 girls, but plans for “a significant expansion” are in motion. In its 2025-2027 budget, Kentucky appropriated $6.5 million for infrastructure modernization at Holly Hill that will fund upgrades to both campuses.
“The Kentucky legislature were incredibly generous and saw that the investment in Holly Hill will be an investment in the community for future generations,” he said.
State Sen. Shelley Funke Frommeyer, R-Alexandria, who worked with Sherry on the funding, noted that persistence is one of his gifts.
“He’s there and asking – asking for time, asking for introductions, asking for an opportunity to present at committee meetings, really putting himself out there,” she said.
She recalls bumping into him in the cafeteria in Frankfort, where he shared a “very compelling story” about a girl who’d attempted suicide. “Sharing such a recent event that rattled him, it rattled me too,” she said. Talking about it with fellow senators helped influence their decision to allocate the capital project dollars, she said.
Goal: Being a national leader
Sherry and Holly Hill have big goals for the residential program moving forward.
“Our vision is that we are going to be the leader in the nation in supporting girls who’ve been trafficked,” he said.
Under Sherry’s watch, Holly Hill is also expanding its supervised visitation program, an upstream preventive program that reunites families.
Beyond the facilities and the programs, Sherry is also improving the culture at Holly Hill, Wilkins said.
“We focus on mental health, and I think James has focused on that in every aspect … (including) making sure that staff are taken care of, because it’s a tough job,” she said. “People who are working with these kids, it takes an emotional toll on them.”
Sherry said he’s taken time to get to know the team of about 60 employees. It’s about “really understanding my workforce and just trying to create a culture where people know they’re valued,” he said.
He’s also focused on external relationships, working to strengthen collaborations and partnerships.
“We’re a small organization; for us to have a really significant impact, we really need to work with others around us,” he said.
For Holly Hill, that means working with school districts, hospitals, higher education institutions and elected officials. And last year, Holly Hill affiliated with Inperium, a nonprofit human services organization with affiliates in 18 other states.
Wilkins said Sherry is well-suited to relationship building. “He treats everyone with the same respect and openness,” she said. “He forms genuine relationships with everybody, no matter where they are in life.”
While he hopes to inspire with his optimism, Sherry said he also cries with staff and helps them tackle day-to-day challenges.
“James is not a guy who’s just an executive on the golf course or in Frankfort. He’s in the trenches with our staff,” Wilkins said. “There is no job too small for James as long as it is helping the kids at Holly Hill.”
‘Lovely to be a steward’
Outside of work, Sherry has “lots of hobbies. There’s not enough time in this world to do all of the wonderful things you can do,” he said.
Among them are hiking and camping with his partner, Anna, who moved with him from New York, and their Welsh terrier. Travel, scuba diving, yoga and his youthful pursuit of swimming – growing up, he was a competitive swimmer and volunteer lifeguard at a surf beach – also top the list. Wilkins, who now considers Sherry a friend, appreciates his interest in new experiences, his sense of humor and his authentic nature.
“I think James is just a caring and genuine person who really does want to make the world a better place,” she said. “He’s not different as a person than he is as the Holly Hill CEO.”
Sherry admits work is never far from his mind.
“My job basically permeates everything,” he said. “I don’t think there’s ever more than a couple of hours that I’m not thinking about something with work. But it doesn’t really feel like work, it’s life.”
He recognizes just how much more there is to do and looks forward to facing the challenges ahead. But he also appreciates Holly Hill’s long history.
“We celebrated our 140th anniversary last year,” he said. “If I’m here until I’m 100, I’ll still just be a small part of this agency’s journey. But it’s lovely to be a steward.”
Discover more from Movers & Makers
Subscribe to get the latest posts sent to your email.