Under the leadership of Jan Hamilton-Crawford, Oakwood offers vibrant, maintenance-free living for older adults
It’s a bitter winter morning. You’re out shoveling snow, trying not to slip on the ice or throw out your back. In summer, it’s the same story—only this time, it’s weeds and humidity instead of snow and ice. Homeownership gets harder as we age, with never-ending chores, surprise repairs and rising expenses.
Now imagine something different: You wake up with nothing on your to-do list except what brings you joy—coffee with friends, a painting class, a walk through the woods. That’s life at Oakwood Village, where residents enjoy a no-maintenance lifestyle and a community designed for living well.
“Oakwood Village enables seniors to live their lives in comfort,” said Jan Hamilton-Crawford, MBA, FACHE, president and CEO of Oakwood Lutheran Senior Ministries. “After moving in, many residents say it was the best decision they ever made.”
Oakwood Village serves more than 1,000 residents across two Madison campuses—University Woods on the West Side and Prairie Ridge on the East. The nonprofit organization has supported the 55+ community for 77 years, offering a full continuum of care: independent living, assisted living, memory care, rehabilitation and skilled nursing.
Set amid peaceful natural settings, Oakwood Village offers not just a home, but a community. Residents can join walking groups, ride a shuttle to the grocery store, play cards with neighbors or relax with a movie. They can sing in a choir, attend lectures, create art or enjoy performances by the Oakwood Chamber Players, an orchestra that performs multiple concerts each year on the Oakwood campuses.
“There’s always something to do or someone to talk to,” Hamilton-Crawford said. “Oakwood is known as a vibrant village where residents live with purpose.”
“I am thankful to be living at Oakwood because of the kindness from all levels of staff, and the availability of help when needed. Oakwood is a community of caring.” – Claire Box, Oakwood Village resident
Hamilton-Crawford, who celebrated her second anniversary at Oakwood last month, leads a team of 700+ employees and oversees strategic planning, operations and long-term growth for both campuses.
She brings decades of healthcare leadership experience to the role. Before joining Oakwood, she served as president and CEO of Trinity Health in Livonia, Michigan, part of a national Catholic health system with 94 hospitals and hundreds of care centers across the country. She previously led operations at CHRISTUS Health System in Texas.
“My background in hospitals and healthcare provided a steppingstone into senior living,” she said. “Everything I did previously prepped me for this role.”
Her career has taken her from the Southwest to the Northeast before landing in Wisconsin. While other job options presented themselves, Hamilton-Crawford chose Oakwood Village because not only was the senior living community appealing, so was Madison. She was drawn to Madison by its lakes and beautiful scenery, ease of getting around the city, proximity to Chicago and Milwaukee, and focus on education, healthcare and technology.
As Oakwood Village’s first Black president and CEO, Hamilton-Crawford is focused on expanding diversity among staff and residents, while continuing to build on the organization’s mission-driven, faith-based roots and service-oriented leadership. In addition, she plans to strengthen Oakwood’s connections with the broader Madison community, fostering relationships that benefit both the residents and the surrounding neighborhoods.
“There’s a big hospitality component to this work that I really enjoy,” she said. “I get to engage with employees, families and, most importantly, residents—every single day.”
She’s particularly inspired by the residents themselves: individuals who have led remarkable lives and continue to contribute to the community.
“I love that I get to serve people who have spent their life working and giving back—pillars in our community,” she said. “Now I get to help them live their best life.”
“I am thankful to be living in a community where residents, staff, managers, and governance officials feel called to collaborate to make Oakwood a place where people thrive.” – Charlie Bunge, Oakwood Village resident
Hamilton-Crawford frequently hears from residents who moved to Oakwood because of a family connection.
“They’ll tell me their parent, grandparent or aunt lived here,” she said. “There’s comfort in choosing a place that’s part of your family’s story. It feels like coming home.”
For Hamilton-Crawford, Oakwood has become home, too. She loves the community and her role in making an impact on the lives of so many people.
“As CEO and president, I am most thankful for the incredible blessings that surround me each day—my family, whose love grounds me; my faith, which guides every decision; and the privilege of serving others through meaningful work. I am deeply grateful for the JOY and laughter that fill my life, especially through my grandsons, Franklin and Hamilton, who remind me of what truly matters. Their energy and spirit inspire me to lead with heart, humility and gratitude and choose JOY in all that I do.”
