The aging services market faces unprecedented workforce challenges, shifting consumer expectations, and complex financial pressures. To forge a path to sustainable success, today’s leaders must operate with strategic foresight and operational agility.
In a recent discussion hosted by WittKieffer Senior Partner Lisa DeSimone Arthur, three distinguished chief executives shared their ideas and insights for addressing today’s challenges and driving organizational resilience and growth. They include:
- Jan Hamilton-Crawford, CEO of Oakwood Village in Wisconsin
- Tyler Kendall, CEO of Westminster-Canterbury of the Blue Ridge (WCBR) in Virginia
- Adam Marles, CEO of Missouri-based EverTrue, formerly Lutheran Senior Services
The following are highlights, insights, and pearls of wisdom from their conversation:
I. Aligning Growth, Agility, and Mission
The current priorities for all three CEOs relate to strategic growth to support long-term sustainability and the need to balance mission with market demands. Adam outlined EverTrue’s four core goals: “fostering a strong internal culture, evolving services to meet changing consumer preferences, pursuing growth through partnerships and investments, and ensuring financial sustainability.” He emphasized the growing demand for customizable, consumer-driven care models, especially as older adults increasingly seek autonomy and flexibility. EverTrue is expanding its life plan communities for affluent seniors while exploring creative ways to serve broader populations.
Jan echoed the importance of aligning services with both consumer and workforce evolution. “We now have five decades of individuals in the workplace,” she noted, highlighting the need for strategies that resonate across generations. At Oakwood, Jan leverages her hospital operations background to focus on core services like independent living and memory care, while partnering with hospitals for offerings like home care and hospice.
Tyler emphasized the importance of reimagining the care continuum at WCBR, guided by the question: “How can we meet [constituents] where they’re at?” This mindset drives strategic repositioning of assets and services to align with evolving needs. Together, these leaders demonstrate that adaptability, innovation, and mission-driven growth are essential to thriving in a rapidly changing aging services landscape.
II. Diversifying Revenue and Optimizing Operations
Financial stability requires a focus on creative revenue diversification and rigorous operational excellence. Leaders must move beyond legacy models and build more resilient financial frameworks. Jan and Oakwood are leasing part of a new skilled nursing facility to a hospice provider, with potential for future expansion. Oakwood is also investing in philanthropy by hiring a chief development officer to grow its foundation. Tyler emphasized the need to “rethink traditional revenue models,” citing WCBR’s Early Advantage program—a low-capital, long-term care insurance product that allows participants to access services from home—as a creative solution.
Philanthropy is another key focus. Adam acknowledged the challenge of attracting donors to aging services, noting, “Donors often gravitate toward causes like children and animals.” Still, EverTrue has found success through education and strategic messaging toward potential donors. “Making the case is really important,” he said.
Operational excellence is equally critical. Jan applies Lean and Six Sigma principles to reduce waste and improve quality, introducing monthly Gemba Walks to engage staff and residents in continuous improvement. “Quality is a given,” she affirmed. Tyler and WCBR outsourced laundry services to improve cost and quality, while Adam eliminated agency staffing by analyzing internal capacity, choosing to “serve the people we can serve with the people who we have trusted to do this work.” The result: improved morale, better care, and reduced costs.
Together, these leaders demonstrate how strategic innovation—grounded in mission and data—can drive both financial sustainability and enhanced service delivery.
III. Embracing New Technologies
Technology integration, personalization, and workforce support are central to how aging services leaders are reimagining care delivery. At WCBR, Tyler has led a multi-year investment in digital infrastructure, including a high-speed fiber-optic network and a full transition from analog to digital communications. “Residents expect streaming and content control,” he noted, underscoring the need to meet modern expectations. WCBR has also introduced robotics for tasks like vacuuming, with plans to expand into dining and guest services, and developed smart rooms to test voice-activated technologies for more personalized living.
WCBR now uses RFID and facial recognition for visitor management, enabling better tracking of campus activity. “Knowing who’s on campus, how often, and how they’re using services will help us continue to expand,” Tyler explained. Artificial intelligence is another frontier. An AI-powered avatar help desk is also in development to assist residents with tech support.
Jan at Oakwood echoed the potential of robotics to address workforce challenges but emphasized, “We can never lose our human touch.” Adam added a note of caution: “How do you filter through the good versus the bad, the bleeding edge versus the leading edge?” EverTrue is piloting avatar-based training for caregivers, simulating real-life dementia scenarios to build empathy and improve care quality.
IV. Engaging the Board
Strong, strategically aligned boards are essential to organizational success, and today’s aging services CEOs are prioritizing deeper engagement beyond traditional governance. Transparency, education, and shared vision are central to their approaches. Adam described his board as “super engaged,” crediting them with asking tough but valuable questions. “I see those questions as a gift,” he said. To foster this relationship, he hosts annual retreats that blend external insights with internal reflection and meets individually with each board member to understand their perspectives and strengthen alignment.
Jan has focused on building a well-rounded board through a new competency matrix, moving beyond legacy affiliations. “We’re not just checking the box,” she explained. She also emphasizes board education, particularly around senior living and union dynamics, and encourages attendance at industry events like LeadingAge and Ziegler conferences.
Tyler has worked to align his board with WCBR’s long-term strategy, including discussions on land acquisition and satellite campuses. He also invites board members to resident events to deepen their understanding of daily operations. “It’s easier for me to come to a board meeting and explain how the operations work when they’ve been there and seen it,” he noted.
For these three CEOs, cultivating an informed, engaged board is a strategic imperative.
V. Building Mission-Driven Leadership and Talent
Building strong leadership teams and cultivating a mission-driven culture are essential strategies for attracting and retaining talent in aging services. The CEOs emphasized emotional intelligence, mission alignment, and intentional culture-building as key to success.
Tyler stressed hiring for compassion over technical skill: “The work is not for everyone,” he said, noting that WCBR seeks individuals who thrive in team environments and can emotionally connect with residents. Jan echoed this, sharing that Oakwood revised its mission to begin with “We are called to serve,” a phrase she uses to set expectations from day one. “It is not a job. You are here to serve,” she tells new hires. She also suggested tapping into retirees to address workforce shortages.
Adam focused on simplifying the hiring process and supporting new employees through mentorship and check-ins during their first 90 days. “How do we make sure that people feel like they can bring their authentic selves to work?” he asked.
Culture is actively nurtured across all three organizations. Tyler starts every meeting with recognition, while Jan hired a dedicated culture and engagement specialist. Adam revamped EverTrue’s values to be more actionable, emphasizing openness and learning: “We had a bunch of words on a wall that meant different things to different people.”
VI. Serving the Middle Market and Sustaining Success
Serving the middle market and sustaining organizational success require innovation, mission alignment, and strong leadership. The three CEOs shared how they are addressing the needs of older adults who fall between low-income and affluent demographics—those often priced out of traditional senior living. Adam acknowledged the challenge: “I personally haven’t seen a middle market residential solution that makes both fiscal sense and quality sense,” but noted EverTrue is expanding home-based care navigation to support moderate-income individuals.
Jan highlighted Oakwood’s sponsorship of AgeBetter, a village-model outreach initiative, and efforts to subsidize services through its 35 sponsoring congregations. Tyler echoed the difficulty of residential solutions but sees expanding home- and community-based services as the “best option” for now.
On organizational success, Jan emphasized deep community roots and leadership continuity. Adam stressed empowerment and accountability: “We want you to make decisions… so long as you are willing to be held accountable.” Tyler underscored authenticity and emotional intelligence: “People can sense when leaders are being real,” which builds trust and resilience across teams. Together, these leaders are redefining sustainability through mission-driven innovation and people-first leadership.
WittKieffer expresses sincere thanks to Jan, Adam, and Tyler for taking time out of their busy schedules to participate in our podcast and share best practices and inspiration with their colleagues in aging services.
For the full in-depth discussion, listen to the full conversation on our Impactful Leaders Podcast episodes:
Impact and Innovation in Aging Services: CEO Stories & Strategies:
