OCTOBER 5–8, 2026
Four days at Cobb Mountain where the wisdom in the room is the curriculum—no keynotes, no panels, just leaders learning from each other.
You’ll leave with new connections, new perspectives, forward progress on your work, and a support system for the next year to keep your work advancing.
The Cobb Mountain Leadership Retreat brings together executive directors, philanthropy leaders, public sector leaders, advocacy directors, board leaders, and mission-driven organizers for four days of peer exchange, deep reflection, planning, and genuine renewal.
October gives social sector leaders a rare window to step back, take stock of where they are, close the year with intention, and arrive at January with clarity, relationships, and a plan.
You’ll leave with progress to finish this year with purpose and enter the next with clarity and direction, and a deepened set of relationships to support you in ongoing connection over the year forward.
This inaugural retreat brings together leaders from across the social sector, creating space for both role-specific conversations and unexpected connections. You’ll gather with your peer group and we’ll also mix it up a lot so we learn from one another. We ask that you come with something you’re working on and be ready to support others in their work. You’ll walk away with solid progress to finish this year and move into the next with strategic focus and direction.
Leading organizations requires vision, resilience, and the ability to navigate constant change. This track creates space for executive leaders to exchange strategies, challenges, and lessons learned with peers carrying similar responsibilities.
Board leadership plays a critical role in organizational health and impact. This track explores governance, partnership with executive leadership, and the evolving role of boards in supporting mission-driven organizations.
Running a company or building a venture can be an isolating pursuit, with few peers who understand the specific weight of the decisions you carry. This track brings you together with fellow builders to think through what's next and sharpen the leadership instincts that grow with you.
Leading in the public sector means balancing competing demands, tight resources, and constant public scrutiny, often with little space to step back and think. This track brings you together with fellow public leaders to reflect on that work and sharpen the judgment it takes to lead well under those pressures.
Fundraising and relationship-building require both strategy and trust. Development leaders will explore approaches to strengthening donor relationships, building sustainable support, and advancing organizational missions.
Fundraising and relationship-building require both strategy and trust. Development leaders will explore approaches to strengthening donor relationships, building sustainable support, and advancing organizational missions.
The retreat is designed around the belief that the wisdom in the room is the curriculum, and that meaningful leadership work requires both strategic clarity and human restoration.
Leave with forward progress on your work, a plan going forward, and a support system for the coming year.
Peer conversations across sectors, roles, and challenges. Structured and unstructured time for honest dialogue with people doing adjacent work.
Field sessions and facilitated reflection to expand perspective and reconnect with the purpose beneath the daily operational grind.
Practical planning time to close the year with intention, clarify what comes next, and return with a stronger sense of direction for the year ahead.
Present your work to the group, receive thoughtful peer feedback, strengthen your commitments, and leave with a concrete plan to finish the year and move into the next with strategic focus and direction.
We’ll establish our ongoing support groups so you can stay in touch over the coming year and continue to deepen your work.
Every leader will leave with a plan of their own making. Here are some of the directions that plan might take. Bring one you’re already wrestling with, or let the retreat point you toward it.
October gives social sector leaders a rare window to step back, take stock of where they are, close the year with intention, and arrive at January with clarity, relationships, and a plan.
You’ll leave with progress to finish this year with purpose and enter the next with clarity and direction, and a deepened set of relationships to support you in ongoing connection over the year forward.
Monday, October 5
Participants arrive Monday afternoon, settle into the property, check in, join the welcome reception, opening circle, community agreements, and family-style dinner.
Tuesday, October 6
A focused day of participatory programming with role-based track sessions, cross-track exchange, free time, connection walks, nature immersion, and family-style dinner.
Wednesday, October 7
A spacious day for open-space conversations, peer learning, reflection, rest, storytelling from the field, and connection around the fire.
Thursday, October 8
Turn your insights into a final Transformation Plan, share it with the group for feedback, and leave with a concrete roadmap for moving forward.
Cleveland is the founder and CEO of the Potrero Group. a leading executive search and strategy firm. An accomplished organizational leader in entrepreneurship and the environment for the past 25 years, Cleveland has worked and consulted widely with startups, businesses, nonprofits, foundations, and governmental organizations. He currently directs the Executive Leadership Program at the University of California, Davis, and he has previously held faculty appointments at UC Berkeley and Georgetown University. He works with hundreds of board members and executives annually.
Cleveland’s expertise spans strategic planning, executive search, business planning, board development, public/private partnerships, entrepreneurship, network analysis, and innovation. He was formerly the executive director of the UC Davis Institute for Innovation and Entrepreneurship and co-founded and served as the founder of the Institute at Golden Gate. He also held executive-level positions at Headlands Institute of NatureBridge (formerly Yosemite National Institutes) and the National Outdoor Leadership School. Cleveland served as board chair of the Marin Community Foundation (over $2 billion in assets), as a board member of Net Impact, an organization with a global network of more than 15,000 leaders who are changing the world through business, and as a commissioner of the Marin County Parks and Open Space Commission.
Cleveland has earned an MBA and a PhD from the University of California, Davis, and is a sought-after thought leader and speaker, regularly presenting at dozens of national conferences.
Mandala Springs is not a typical conference venue, and that is precisely why it was chosen. Set on 200 acres of forest and meadow in the Mayacamas Mountains, it offers a sense of place that invites slowing down, clear thinking, and deeper connection.
Take a moment to relax on the terrace and enjoy the sweeping views of Cobb Mountain. The open-air seating invites participants to pause, reflect, and absorb the natural beauty that surrounds Mandala Springs, creating space for quiet contemplation and renewed energy
Gather with peers in Mandala Springs’ lush outdoor spaces for thoughtful conversation, shared learning, and reflection. The environment encourages authentic connections, informal discussions, and meaningful exchanges, making every moment outside as impactful as the sessions inside.
This retreat is intentionally designed to be distinct from a traditional conference. Rather than centering on a packed agenda of speakers and presentations, it creates space for meaningful conversation, reflection, and connection in a beautiful natural setting. We are thoughtfully designing the experience to feel open, grounded, and deeply valuable — where the wisdom, challenges, and perspectives of the leaders in the room become the foundation for learning and growth.
Pricing and lodging details are being finalized. The all-inclusive retreat fee is expected to include programming, facilitation, lodging, and meals from Monday dinner through Thursday lunch. A dedicated Logistics and Pricing page will provide full lodging options and registration details.
Farm-to-table vegetarian and vegan catering is included.
Mandala Springs is located at 14117 Bottle Rock Rd, Cobb, CA 95426, approximately one hour from Santa Rosa and about 90 miles north of San Francisco.
The Cobb Mountain retreat sits near some of Northern California’s most extraordinary places, including Napa and Sonoma wine country, coastal redwoods, the Sonoma and Mendocino coast, natural hot springs, and Clear Lake.
Sign up for updates about the Cobb Mountain Leadership Retreat, application details, program announcements, and future Potrero Group gatherings.
Join a limited-capacity four-day gathering for social sector leaders ready to think together, reconnect with purpose, and return to their work with renewed energy.
