Meet Cleveland Newcomer Jessica Dennsteadt: Adventure Awaits in Hudson

by | Nov 4, 2026 | Newcomer Profiles, Recruitment & Relocation

Dennsteadt family posing with the downtown Cleveland skyline in the background
The Dennsteadt family embraces their new home in Northeast Ohio with the downtown skyline in the background. Photo courtesy of the Dennsteadt family.

For Jess and Dave’s family, moving has always been part of their story.

Their family motto is “Adventure awaits,” a phrase coined by one of their sons that has even made its way onto family T-shirts. It is fitting for a family that has built a life in several very different places. Before Northeast Ohio, they called both New Jersey and Paris home.

From Paris to Northeast Ohio

Jess and Dave first moved to Paris shortly after they were married. That began a pattern of embracing new places and experiences together.

Years later, the family returned to Paris, this time living in the heart of the city near the Eiffel Tower. Moving from an American suburban community to central Paris gave their children an entirely different experience. It also reinforced a lesson Jess and Dave have tried to teach them throughout their lives. New places offer opportunities to learn.

When Dave, who has spent much of his career with RPM, was offered an opportunity with the company in Northeast Ohio, the family began considering a move.

Although Dave had traveled regularly to Medina for work, Jess admits they knew surprisingly little about the region. She had typically handled much of the research for their previous moves, but relocating from Paris with two older children made this move different.

This time, they relied on Executive Arrangements for help understanding the schools, neighborhoods and communities that would best suit their family.

A Familiar Feeling in Hudson

After experiencing life in both suburban New Jersey and central Paris, the family wanted a community that would work for everyone. Hudson quickly stood out because it reminded them in many ways of Haddonfield, the New Jersey town where their children had grown up.

Jess appreciated having someone who could help them understand not only the geography of Northeast Ohio, but also the personalities of different communities.

That local perspective helped the family narrow what initially felt like an unfamiliar region into an inviting place they could realistically picture calling home.

Choosing Schools While Overseas

Schools were another major part of the decision. Jess and Dave gave their boys 51% of the vote in choosing the schools they wanted to attend.

Jess had worked in education for years, including as an English as a Second Language teacher. That experience helped her know what to look for when visiting schools.

Jess and Dave initially visited the area without their children before Dave formally accepted the position. The following spring, they returned with the kids to tour schools and communities together.

For their older child, they ultimately chose Western Reserve Academy in Hudson. Jess was impressed by its high academic expectations as well as its emphasis on students’ social and emotional well-being. She also liked the independence it encourages. She describes the experience as a helpful bridge between high school and college.

Their younger child entered an elementary school within the Hudson City School District, which gave the family another immediate connection to the community.

Discovering Northeast Ohio

Jess and Dave Dennsteadt with their two sons outdoors in Northeast Ohio during fall
Jess and Dave Dennsteadt with their sons, enjoying fall in Northeast Ohio and the sense of community they have found since moving to Hudson. Photo courtesy of the Dennsteadt family.

Not everything about the transition has been easy. Jess says this move has been harder than some of their previous ones because their children are older and their lives were more established.

But the family has approached Northeast Ohio much the same way they approached Paris—by getting out and experiencing it.

A friend once advised Jess that whenever you move somewhere new, you should “try everything and go to everything.” The family has taken that advice to heart.

They have attended professional sporting events, sampled local ice cream, and explored restaurants. They have also gone camping and enjoyed the region’s outdoor activities. They have become Cleveland Cavaliers fans, discovered that Mitchell’s Homemade Ice Cream is their go-to, and found favorite places throughout the area.

Jess has also been surprised by Northeast Ohio itself. She loves the breathtaking sunrises and sunsets, the changing colors, and how accessible everything feels. The quality of the region’s museums, healthcare, schools, cuisine, and cultural institutions exceeded her expectations.

She has been especially impressed by the cultural diversity of Greater Cleveland. Jess came to Northeast Ohio from the East Coast with a background in English as a Second Language (ESL) education. She has enjoyed learning about the immigrant communities, faith traditions, and cultures that have shaped the region. She did not expect to find such a broad mix of Jewish, African American, Catholic, and immigrant communities in Greater Cleveland.

“It’s an underrated city,” she says.

Finding Community by Showing Up

Jess is equally candid that establishing a life somewhere new takes effort.

She grew up in a large Italian family in Queens surrounded by cousins, so making friends intentionally was not something she needed to think much about when she was younger. Moving away and building lives in different places changed that.

After settling in Hudson, Jess took a job as a school aide, which helped her meet students, teachers, and other families in the Hudson City School District. Their children have helped the family build connections in different circles. Their older son attends Western Reserve Academy, while their younger son attends a Hudson elementary school. Sports, Scouts, church, and other community activities have created even more opportunities to connect. Jess has also found a welcoming expat community. It has added another layer of connection and helped the family develop a stronger sense of belonging in Northeast Ohio.

Advice for Other Newcomers

Her advice to other newcomers is simple—show up.

Volunteer, attend events, and try something unfamiliar. Look for places where you will see the same people regularly. Those connections, whether through school, houses of worship, work, or community activities, are often what begin to make a new place feel familiar.

Jess shares that building a new life can be exhausting. “If it’s exhausting, you’re doing it right,” she says.

She also credits Executive Arrangements with helping the family get established and giving them a starting point in a region they knew very little about.

For a family that has lived very different lives in very different places, Hudson is simply the newest chapter in a much larger story.

After all, “Adventure awaits.”

At Executive Arrangements, we help new hires and their families settle into their new community by helping them cultivate relationships. Think of us as community consultants and network experts. Learn how Executive Arrangements helps candidates considering a relocation. Contact us online or call at 216.231.9311.