9/19/2026
Fleurish
Lead With Heart
We’re exploring human-centered leadership through literature with Jessica DePinto, Wisconsin. Together, we’ll consider what it means to lead and how effective leaders create impact through connection, authenticity, and resilience.
We’ll explore these themes in our own lives and in those of the book Lillian Boxfish Takes a Walk by Kathleen Rooney. Don’t fret if you don’t have time to read the book. You can bookmark this five-minute read about the trailblazer who inspired the Lillian Boxfish character. Or just show up ready to reflect on your career, accomplishments, and leadership along the way.
See you Monday, Oct. 19, at 8 p.m. ET / 6 p.m. MT!
MEET YOUR HOST
Jessica DePinto, Wisconsin, is a strategic, mission-driven leader with a career spanning law, professional services, higher education, and nonprofit leadership. She has a breadth of experience in organizational effectiveness, culture, strategy, and executive partnership — grounded in a legal foundation and strengthened through senior leadership roles.
Jessica’s professional journey began as a lawyer. She later expanded into strategy and operations at Deloitte, advising organizations navigating transformation, compliance, and growth. Her commitment to impact-focused work led her to nonprofit leadership roles, where she guided teams, built cross-sector partnerships, and advanced education-centered initiatives.
In higher education, Jessica has served as a senior advisor and Chief of Staff, supporting institutional strategy, board relations, and enterprise-wide initiatives. At Loyola University of Chicago, Jessica serves as an adjunct professor of law and business ethics, teaching courses on the regulatory environment of business and helping students connect legal principles with real-world organizational challenges.
In every role, Jessica is known for bringing clarity to complexity, building strong relationships, and aligning people, processes, and purpose to drive meaningful results.
In every role, Jessica is known for bringing clarity to complexity, building strong relationships, and aligning people, processes, and purpose to drive meaningful results.
Jessica earned her M.A. in Italian language and literature. She loves returning to Italy — she speaks fluent Italian and holds dual citizenship — to explore the cities, the countryside, libraries, unique bookstores, and, of course, the contemporary literature.
alumna events
Fleurishing Together
This virtual event is part of Fleurish, an event series for alumnae. Your commitment to alumnae dues makes programs like this possible.