Naples’ Leading Lady of Philanthropy

Dena Rae Hancock dedicates her personal and professional life to serving others.

BY November 1, 2023
Dena Rae Hancock
Dena Rae Hancock (Photo by Christina Bankson)

The first time I meet Dena Rae Hancock, she’s wearing a sunshine yellow business dress. The second time I see her, on Zoom, she’s in her Naples home office, in front of a brazen, hot pink wall. “Oh, I love pink,” she says, unabashed. “It’s a color that brings that happy feeling.” (Her electronic avatar is a grinning blonde ringed in bubblegum pink.)

Some will accuse me of being corny, but I’ll go ahead and say it: There’s a vibrancy to Dena Rae, and it goes well beyond her color palette. For those who don’t know her, Dena Rae is both a philanthropist—she and her husband, Rob Caito, have given to numerous causes in Naples and their native Indiana—and a philanthropy professional who has worked for and on behalf of universities and nonprofits, including the Golisano Children’s Museum of Naples (CMON), and with The Naples Trust Company, where she helps clients shape their legacies. She treats the career as a calling, a means of helping people figure out how they wish to better the world. “Everybody, I believe, wants to help,” she says. “Your dollar and my dollar combined can help us produce something together that changes lives.”

Dena Rae did not set out to become a fundraising professional. She planned to be a teacher, like her dad. As a senior at Indiana University (IU), she intended to accept a teaching job in her hometown high school outside of Chicago. Until, one day late in the spring semester, IU president Tom Ehrlich summoned her out of class. “Would you do me a favor?” Dena Rae recalls him asking when she arrived—perplexed—at his office. “I’ve got a job interview lined up for you. I would love for you to take this job; I think you would be perfect.”

Even on a 36,000-student campus, Dena Rae made her appearance felt. She gushed school spirit, the daughter of an IU grad who never considered going anywhere else. As student body president, she led a push to build a campus recreation center, a project requiring legislative approval. In her home office, she keeps a sketch of the center with a note from its first director: “You had the vision for what this could be before it ever was,” it reads. The job Tom had in mind was a research position helping Robert Payton, founder of IU’s Center for Philanthropy, lay the groundwork for the Indiana Campus Compact, a five-college network focused on service learning. This educational model challenges students to tackle real-world situations and connects them with civic organizations to the benefit of both. Tom had lobbied for her, impressed by her spunk, leadership, and training in political science and education.

Dena Rae accepted, and so began a life in philanthropy and service. By 23, she was the Compact’s executive director. If the job, which required her to report to five university presidents, was daunting, she doesn’t let on, even today. “I was never shy,” she says with a grin. I believe that. Dena Rae radiates an ‘I-am-who-I-am’ kind of authenticity.

About five years later, life as she knew it halted. She was married then, with 4- and 1-year-old sons, and had shifted into full-time motherhood. Her husband, Brian Hiltunen, suffered a diabetic attack brought on by his Type 1 diabetes. He died in his sleep. The next day, she went to the grocery store, low on milk. She didn’t tell anyone what had happened. Instead, with an empathy exclusive to those who’ve suffered tragedy, she gazed at other shoppers and wondered what sadness and stories they might carry. “That experience, that feeling in the middle of the dairy department, is never very far from me. You just don’t know what other people might be going through,” she says.

She also realized that the neighbors who rushed to help her found joy in doing so. “Sometimes people don’t want to accept help. But in accepting the help, you don’t know how you are helping someone who is giving.” Philanthropy, she says, is much the same.

Dena Rae Hancock wasn’t looking for a new relationship when Rob Caito dropped into her life. They met on a soccer field where their 4-year-olds were teammates. Rob, a divorcé with three children, was the “team dad.” At first, Dena Rae thought she had little in common with Rob, an executive, whose family ran a major produce distribution business. But they were grounded in their shared Midwestern values, a belief in service, and similar visions for their and their children’s futures. Her wedding ring is in Indiana U red and white and blends their clans: diamonds signifying their girls, rubies, the boys. Two rubies are from her first wedding band—Rob’s idea. The couple had two more children together.

“Our first philanthropy was at home,” Dena Rae Hancock says. When their children were young, she and Rob gave each a bank with three slots—for saving, spending and donating. In 2017, the couple decided to share their family principles more broadly, establishing the Hancock Hiltunen Caito Center for Leadership and Life Skills at IU. The center, located in the football stadium, focuses on building character and financial literacy among student athletes. “It’s about how do you build a life that’s stable so that you are in the strongest position to go out and help others,” she says.

Dena Rae intended to retire when the family moved to Naples in 2017. She had done big things—served as vice president of advancement at Marian University in Indianapolis and director of major gifts at the Indianapolis Zoological Society, and chaired the women’s philanthropic arm of Indiana University’s $3 billion bicentennial campaign.

Then, she discovered CMON. “I don’t know if this is a Gulfshore Life-worthy story,” she says, a little ruefully. “But the honest-to-God, real story of how I got involved is I heard that Kevin Bacon was coming.” The actor and musician was supposed to headline a CMON benefit, and Dena Rae, who’d met him previously at a concert, is “his No. 1 groupie fan.” She phoned the museum and insisted on reserving a table. Museum director, the late Karysia Demarest, curious about the enthusiastic stranger, invited Dena Rae to tour the museum. 

Kevin Bacon never made it to Naples; CMON instead got its first chief advancement officer. “It was unlike any job I’ve ever had,” Dena Rae Hancock says. Seeing the kids—and especially kids and their parents together—made her light up. “It is the most joyful job I have ever had.” (Side note on Kevin Bacon: Rob hired him with his brother’s band, The Bacon Brothers, to perform for Dena Rae’s 50th birthday.) At CMON, Dena Rae’s fundraising helped establish scholarships for summer programs and discounted admissions for lower-income families. She took over as CEO when Karysia fell ill, steered the museum through the pandemic, and then transferred the helm to chief operating officer Jonathan Foerster, remaining in an advisory role. Last year, she transitioned to senior vice president of wealth services at The Naples Trust Company, where, with the attentiveness of a counselor or a minister (she once served as a part-time youth pastor), she listens to clients talk about their lives, their passions, and how they envision shaping the future. But she couldn’t resist the kids.

A short while ago, Jonathan asked her for recommendations for a newly created senior philanthropy officer position. When she described a candidate, he realized she was talking about herself. “This is just where her heart is,” Jon says. “She’s the ultimate people person. She’s great at meeting you where you are and leading you to the place where you’re going.”

Dena Rae now navigates the CMON role while maintaining a presence at Naples Trust. “I am definitely the type of person who has a hard time sitting still,” she says, laughing. She and Rob are first-time empty nesters this year, and she means to fill the parenting void by nurturing causes. She serves on several boards at IU, on the Women’s Foundation of Collier County and Naples Children & Education Foundation, and is active in Emmanuel Lutheran Church, where she, unsurprisingly, serves on a fundraising committee. Dena Rae is also co-chairing two major galas this season. The first is for the STARability Foundation, a group she came to know and love during her first stint at CMON. The organization works with people with developmental and intellectual disabilities.

The second is for the Juvenile Diabetes Research Foundation (JDRF), a cause that anchors their family. Ten years ago, Dena Rae Hancock nearly lost her son Caleb the same way she lost his father. He’s thriving now, about to set out on a European tour with his band. “My husband and I are so honored to be chairing this event this year,” she says. “We are so close to a cure.” 

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