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

Biography & Founder’s Journey

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, governance, strategy, next-gen succession, finance, and organization development, having designed mission-driven strategies for private foundations with assets ranging from $100 million to $2 billion.

Most recently, Sylia was the founding Executive Director of the Winston Family Foundation, where, in partnership with the board, she envisioned, designed, and launched Project One Health, a $21M, multi-year initiative combating the epidemic of youth mental health linked to excessive screen time and an indoor lifestyle. She designed a nationally replicable model that serves over 1,000 youth annually and utilizes grants, PRIs, public service campaigns, convenings, cross-sector partnerships, and capacity-building to maximize Winston’s impact and reach.

Before Winston, she served as Vice President of Operations & Finance of the Arthur M. Blank Family Foundation, supporting a multi-generational family foundation and the philanthropy of the Blank Family of Businesses: the Atlanta Falcons, Atlanta United, Mercedes-Benz Stadium, PGA Tour Superstores, and Montana Ranches. She was pivotal in supporting Arthur Blank’s most significant legacy grant investments of hundreds of millions of dollars, scaling the organization to deliver on Arthur’s 10-year, $1.5B giving pledge and fulfilling a complex portfolio of grants, PRIs, in-kind grants, direct charitable activities, and employee giving.

  • As the founding President & CEO of the Roy & Patricia Disney Family Foundation, she partnered with the family’s 25-person, multi-generational board to develop and launch LA’s newest progressive family foundation dedicated to creating an inclusive society and economy for the most vulnerable. With an initial endowment of $150M and an annual budget of $7.5M, Sylia built a values-based family enterprise with extensive family engagement and cohesion.

    Disney prepared her for creating The Generative Group, Sylia’s consulting practice serving as a trusted advisor to ultra-affluent families and their family offices. Through her firm, she has launched three new values-aligned family foundations, each in the $100M to $400M range. She also co-created Think Money First!, a board and executive training and coaching program on full-cost budgeting, fundraising, high-performing governance, and change management, to strengthen over 250 grantees' CEOs and board chairs.

    Sylia credits her expansive knowledge of the power of philanthropy to the 8 years she served as the Chief Operating Officer at the Annenberg Foundation, a $1.6B multi-generation family foundation with an annual grant budget of $80M and 90 staff. She launched the Foundation’s headquarters in Los Angeles, scaled operations, and built the management team. She then pivoted to spearheading innovative initiatives and programs, including the Annenberg’s $35M/year responsive grantmaking program; the Annenberg Space for Photography, LA’s newest cultural destination, with over 150,000 annual visitors; Annenberg Alchemy, a nationally recognized nonprofit leadership and board development program that trained over 2,000 nonprofit CEOs and board chairs; and LA n Sync, a regional cross-sector collaboration securing over $300M in federal and philanthropic investment for Los Angeles.

    Her dedication to nonprofit capacity-building stems from her firsthand experience delivering life-changing education services to foster youth and their caregivers while serving as Vice President of Human Development & Youth Services at The Community College Foundation. Under her leadership, over 150 staff carried out 11 distinct social welfare programs serving over 15,000 foster youth and their caregivers across 55 community colleges. Recognizing the importance of quality front-line caseworkers, she launched a fee-for-service, nationally recognized Training Institute that delivers strength-based, family-centered training and certifications to over 1,000 county agency personnel annually.

    She continued championing the importance of nonprofit board leadership, effectiveness, and financial sustainability as the interim CEO of Asian Americans Advancing Justice SoCal. Together in partnership with the board and staff, they led the successful financial turnaround of one of the nation’s largest legal aid organizations, with over 100 staff and an annual operating budget of $15M. Her leadership stabilized the organization’s financial health and allowed it to recruit and onboard its permanent CEO.

    Sylia’s business acumen comes from her career at Arthur Andersen, LLP, where she honed her financial and tax expertise as a CPA for 6 years. She then pursued an MBA 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

    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

  • Angie Jean-Marie

    Fait La Force Strategies

    Grantmaking Strategy
    Multi-generational Engagement
    Social Impact Campaigns.

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  • Hanne Volkaerts

    Creating Curiosity

    Marketing Strategy
    Creative Production
    Advertising

Our Clients

We maintain confidentiality agreements with our clients, however, the following are a sample of our clients we can share.