On October 1, 2026, WesleyLife welcomed Anna Callender as its new chief operating officer. Anna brings more than two decades of senior living experience and a leadership philosophy centered on helping people feel “seen, heard, and valued.”
Prior to joining WesleyLife, Anna served as vice president of operations for The Aspenwood Company in Houston, Texas, providing leadership across multiple communities. Her career has spanned operations, sales, and growth in levels of living including independent, assisted, and memory support and care.
Throughout her career, Anna has led large, multi-community portfolios, helped communities achieve significant gains in occupancy and financial performance, developed team members into leadership roles, and led initiatives designed to strengthen memory care and the resident experience.
Her background in both sales and operations also has shaped her perspective on the connection between exceptional experiences, strong organizational performance, and sustainable growth.
But for Anna, leadership begins with relationships.
“I do my best work when I’m helping people feel seen, heard, and valued,” she says.
That means listening, meeting people where they are, and communicating in ways that resonate. Her approach aligns closely with WesleyLife’s focus on creating environments where people feel respected, connected, and able to thrive.
Anna also sees strong alignment between her experience and WesleyLife’s direction. She is particularly excited about the organization’s continued growth and innovation, its focus on education and well-being, and its commitment to developing and promoting people from within.
Anna will collaborate closely with leaders across the organization, bringing deep operational expertise, high expectations and accountability, and a strong belief in the role relationships and culture play in organizational success.
"Anna's combination of operational experience, curiosity, and relationship-centered leadership will help support WesleyLife as the organization continues to grow, innovate, and revolutionize the experience of aging," Allison Pendroy, WesleyLife's president and CEO, says. "We are fortunate to have her with us."
