Professional Retreat for
Experienced Women Enrollment Leaders
June 21-24, 2026
Harmon Guest House in Healdsburg, CA
The Lookout is more than a conference. It’s a curated space for the kind of insight and connection that only emerges when we step outside of our daily work. Together, we’ll explore our leadership journeys, sharpen our “signature presence,” and unpack real dilemmas and opportunities shaping our roles.
Our facilitator, Crystal Land, former Head of School at Head-Royce and a partner at Leadership + Design, will guide us through a blend of inner work, shared learning, and practical tools to support continued growth. And yes: there will be time to rest, laugh, and enjoy the beauty of wine country!
About Crystal Land, Retreat Facilitator
Crystal Land (she/her) is a Partner at L+D. Crystal has spent her career as a leader in independent schools and as a facilitator with schools and teams. Prior to joining L+D, Crystal served as Head of School at The Head-Royce School in Oakland, where she also served in a variety of roles from Assistant Head of School and Admissions Director to English teacher over her 30+ year career. Over the past two decades, Crystal has designed and facilitated workshops for school leaders in the Bay Area and nationwide on topics including strategic planning, developing capacity in leadership teams, school governance, writing and meditation and women in leadership. She writes articles and thought pieces for various publications and has presented locally and nationally on effective school leadership.
Crystal has served on the Boards of the Global OnLine Academy, the Seven Hills School, the CAIS Secondary School Accreditation panel, Vincent Academy, and the California Teacher Development Collaborative (CATDC); she is currently a trustee at Marin Primary and Middle School. She holds a M.A. in English from Middlebury College, a M.A. in Education from Stanford University and a B.A. from U.C. Berkeley in English and Political Science. She appreciates big messy problems and truly enjoys helping leaders and schools find ways to successfully navigate them. She and her husband lives in Marin, CA and are the parents of two adult children and one beloved dog.
About Dana
Dana Nelson-Isaacs has spent more than 25 years helping schools thrive. Known for her thoughtful insight and candid, collaborative style, she partners with admission teams, heads of school, and boards to strengthen enrollment strategy, communications, and community engagement. Dana's professional journey spans a wide range of institutions, including K-12, boarding and day, and single- and all-gender schools. Before launching her consulting practice in 2013, she held key roles in enrollment and marketing. A dynamic speaker and facilitator, she leads workshops and speaks regularly at conferences. Dana also facilitates The Assembly, a mastermind group for school leaders, and provides one-on-one and team-based executive coaching. She lives in Northern California with her husband and their high-school-aged daughter.
About Harmon Guest House
The Harmon Guest House is an elegant, modern sanctuary situated just steps from the historic Healdsburg Plaza in the heart of Sonoma Wine Country. This is more than a venue, it's a creative retreat, where locally-sourced art and thoughtful design elevate every conversation.
