Cases
While every person and family is unique, there are themes and experiences common on the giving journey. Combining our experience working with generous people and families, with what we know from research in the field, we help our clients give, learn and govern with purpose, clarity and confidence.
Reigniting a Generational Legacy
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The Sterling family, led by the third-generation. Their 50-year-old family foundation had become inactive, its mission outdated and its board paralyzed by inter-generational conflict.
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The foundation, once a source of family pride, had become a point of contention. Younger family members felt disconnected from its original purpose, while senior members resisted change. The family’s philanthropic leadership was at risk of fading away due to neglect and unresolved disputes.
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Sharilyn was engaged to help the family make decisions about the future. Confidential interviews with each family member clarified shared desire to fix what wasn’t working. A feedback session with the family helped them identify where they needed and wanted to start. Sharilyn facilitated a retreat focused on revisiting the founder’s original values, and exploring what the family wanted the foundation to be today and what the role of the family would be. This created common ground to discuss a new vision and mission that honored the past while reflecting the passions of the current generation. Crucially, she helped them establish new governance architecture with clear roles and responsibilities so they could work more effectively together.
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The Sterling Family Foundation moved forward with a shared mission and a fair governance structure, inspiring greater engagement by interested family members. Granting resumed with a renewed sense of purpose, and the family’s legacy of giving emerged stronger and more unified than before.
Engineering a Young Family's Giving
Client Profile
Jackson, a 38-year-old tech founder, and his wife. With young children at home, Jackson worried about the longer-term impact of his financial success on his family and wanted to model generosity for his kids.
The Challenge
While passionate about giving back, Jackson’s schedule was demanding. He knew little about structured philanthropy and felt overwhelmed by the options. His primary goal was to create a simple, effective giving strategy that could grow with his family and instill philanthropic values in his children from a young age.
Watermark’s Role
Sharilyn helped Jackson translate his intentions into action. They started by identifying the family’s core values and interests, which centered on education and access to technology for underserved youth. To maximize simplicity and flexibility, Sharilyn recommended establishing a donor-advised fund (DAF), allowing Jackson to make a tax-deductible contribution immediately while deciding on specific grants over time. Sharilyn then helped them create "family giving" rituals. Each quarter, they set aside a small amount in the DAF for the children to "grant" to a charity of their choice after researching it together as a family.
The Outcome
Jackson now has a formalized, low-maintenance philanthropic plan that aligns with their values. The DAF provides an easy framework for his giving, and the quarterly practice has made philanthropy a tangible concept for his children. He feels confident he is building a meaningful legacy of generosity.
Launching a Legacy
Client Profile
David and his wife, Sarah, have three successful adult children, all with their own families. They recently sold the family business, within which two of the three children had been actively involved.
The Challenge
David and Sarah wished to create a family foundation to serve as an anchor for the family after the sale of a business. They hoped everyone might participate, but feared the foundation might become a passive parental project rather than a dynamic, multi-generational experience.
Watermark’s Role
Sharilyn helped David and Sarah clarify their hopes, aspirations and concerns. She also had conversations with each of their children (and spouses) to assess their appetite for involvement. The children had been concerned about losing family connection with the sale of the business so were eager to have a new touch point for the family. Sharilyn helped them identify shared values and a vision for their philanthropy as a family. This discussion allowed the siblings (and their spouses) to connect their own passions to their parents' goals. With a shared vision established, Sharilyn helped them draft a mission statement and a governance structure that clarified approaches to decision making. And a Giving Club was created for the grandchildren to learn about philanthropy through small grants.
The Outcome
The foundation launched with a clear, collaborative mission that excited the entire family. The structure provided a roadmap for effective giving and leadership succession, ensuring the family’s legacy of generosity into the future.
A Focused Philanthropic Finale
Client Profile
Jamil and Pearl, a couple in their late 60s with significant capital from a business sale. Both are experienced non-profit board members. Their adult children are not involved in their philanthropy.
The Challenge
Following the sale of their business, Jamil and Pearl felt overwhelmed by their new capacity for giving. Their goals were to make a substantial impact and spend down their charitable assets within 15 years. They needed a strategic plan and the right charitable vehicle to achieve this without creating a permanent foundation.
Watermark’s Role
Sharilyn guided them through a structured process to help them focus their vision on two passions: children’s mental health and workforce development. Next, she reviewed the pros and cons of using a donor-advised fund (DAF), which the couple chose for simplicity and lower overhead. Sharilyn helped create a 15-year spend-down plan. In addition to organizations where Jamil and Pearl had a history of involvement, Sharilyn vetted and opened the door to new high quality charitable partners in their identified giving areas.
The Outcome
Jamil and Pearl now have an actionable roadmap. The DAF structure minimizes administrative complexity, and their strategic plan provides confidence that they will have an impact within their desired 15-year timeframe.
Strategic Giving for the Global Leader
Client Profile
A time-poor CEO with a deep commitment to promoting STEM education for girls.
The Challenge
The CEO’s demanding schedule left no time for the research and due diligence required for impactful philanthropy. Her giving was often reactive and she worried her contributions weren't achieving their full potential. She needed a trusted partner to build and execute a long-term strategy that reflected her vision.
Watermark’s Role
Sharilyn conducted a series of concise, focused meetings to distill the CEO's goals into a multi-year giving plan. Sharilyn then identified and vetted high-impact charitable partners in the client's interest area. The CEO narrowed these to a shortlist, empowering Sharilyn to engage them to identify opportunities for new charitable investments. Sharilyn managed the relationships and granting process, requiring minimal time from the CEO.
The Outcome
The CEO now has a comprehensive giving strategy that is managed on her behalf and allows her to engage at a high, strategic level without getting lost in operational details. She is confident her resources are fueling organizations making a measurable difference, turning her philanthropic vision into a powerful reality.