Who We Are

Sylia Obagi

A rare combination of financial acumen, strategic insight, and a passion for impact.

Architect of family foundations ranging from assets of $100M to $2B.

Strategist

Innovator

Collaborator

Problem Solver

Generative Leader

Sylia Obagi

Sylia Obagi is a transformative leader, innovator, and coalition builder in philanthropy. With a rare combination of financial acumen, strategic insight, and a passion for impact, Sylia Obagi is redefining what it means to lead with purpose in philanthropy. As the Founder of The Generative Group, she partners with donors, family foundations, and social-purpose organizations to align their core values with bold and meaningful philanthropy. Sylia is a recognized expert in family philanthropy and governance, having designed mission-driven strategies for private foundations with assets ranging from $100 million to $2 billion. (See a sample of clients)

Most recently, Sylia was the founding Executive Director of the Winston Family Foundation, leading its board through a strategic planning process that resulted in Project One Health—a $21 million, multi-year initiative that redefines youth well-being by reconnecting young people with nature in an increasingly tech-driven world and indoor childhood. This nationally scalable model integrates cross-sector partnerships, grants, and direct charitable activities.

Before Winston, she served as Vice President of Finance & Operations of the Arthur M. Blank Family Foundation, overseeing its $150 million annual budget, impact investments, and direct charitable initiatives. She was pivotal in supporting Arthur Blank’s most significant grant investments and structuring the foundation to serve the multi-generational Blank family and its diverse business ventures, including the Atlanta Falcons, Atlanta United, Mercedes-Benz Stadium, and PGA Tour Superstores.

Her expertise extends beyond philanthropy into nonprofit leadership. As interim CEO of Asian Americans Advancing Justice – SoCal with over 100 staff and a $15M/annual budget, she led the turnaround of one of the nation's largest legal aid organizations, navigating financial challenges, labor negotiations, operational restructuring, and fundraising to restore fiscal health and programmatic strength.
Sylia led the creation of an important new funder as the inaugural President & CEO of the Roy & Patricia Disney Family Foundation. With an initial endowment of $150M and an annual budget of $7.5M, she worked closely with the multi-generational board to establish a leading social, economic, and environmental justice grantmaker.
She was an architect and builder as the second-most senior executive at the Annenberg Foundation. She established the Foundation’s Los Angeles headquarters and grew staff from 13 to 90 people. She was the principal architect of the Foundation’s $30M/year VISION+ grantmaking program. She led the launch and management of the Annenberg Space for Photography, LA’s newest cultural destination, with over 150,000 annual visitors. She created Annenberg Alchemy, a nationally recognized nonprofit capacity-building program that trained over 2,000 nonprofit leaders. Sylia designed a regional cross-sector collaboration known as LA n Sync that secured over $300 million in federal and philanthropic investment in Los Angeles.
Sylia understands the vital importance of nonprofit effectiveness and financial sustainability through her leadership as the Vice President of Human Development & Youth Services at The Community College Foundation. Under her leadership the organization’s 100-person staff delivered education and social services across 55 community college campuses to over 15,000 people annually.
She started her career at Arthur Andersen, LLP, where she honed her financial and tax expertise as a CPA for 6 years. She holds an MBA, specializing in strategy, from UCLA’s Anderson School of Management. She is a certified governance and executive coach (BoardSource, IPEC, ICF), and a highly skilled change-management facilitator, trained by Robert Gass, Founder of the Social Transformation Project and Rockwood Leadership Institute.
Sylia is an active voice in the sector, serving on advisory councils, speaking at national conferences, and mentoring emerging philanthropic leaders.

Accomplishments

Sylia has been an executive leader for over 20 years leading and scaling private foundations and their philanthropic strategies.

Sylia has launched cutting-edge initiatives, projects, and place-based collaborations that have achieved significant impact.

Our Partners

Sylia is complemented by a team of highly skilled, best-in-class issue-area specialists or business functional expertise who are engaged to help clients achieve their unique goals and priorities.

Experts join the engagement based upon the client’s desires and agreed upon roadmap.

Bill Chiaravalle

Brand Navigation
Branding
Visual Storytelling
Website & Digital Media
Deborah Chay

OE Consulting
Strategic Expertise and Support for Family Offices
Talent Recruiting
David Greco

Social Sector Partners
Nonprofit Financial Sustainability
Nonprofit Capital Strategies
Laura Phelps

StoryLens PR
PR
Media Strategy
Narrative Storytelling
Dave Sternberg

Loring Sternberg
Governance Strategies
Major Gift Development
Capital Campaigns