Working with Watermark
We work with generous people, families and organizations to help them give, govern and lead with purpose, clarity and confidence. You are accustomed to getting the best possible advice. Here are four reasons you might seek our help:
1. You need a place to start
You’ve made charitable donations in the past but perhaps due to the sale of a business, retirement or inheritance, your capacity to give has increased significantly. Giving back is a major priority but you may feel overwhelmed about where to start.
2. You want to engage family effectively
You want to involve your family in giving for the first time, or already have a long tradition of family philanthropy but are stuck. You may be anxious to begin, wrestling with complexity and conflict, or navigating family transition. You want the family to be aligned for a productive and purposeful experience.
3. You dream for impact
You have a history of giving but wish to be more intentional. Or you want to make a major charitable investment but aren’t sure how to navigate the details to ensure the results will be there.
4. You desire deeper understanding and connection
You have a particular interest for your giving but are not familiar with the landscape, leaders or organizations in that space. You want to connect with charitable peers and networks, or access learning experiences so that you have the information and relationships you need to realize your objectives.
We’re your trusted guide and put purpose at the centre of your giving.
Wonder what a philanthropy advisor does and what they need to know to be able to do it well? Explore this competency framework so you can better assess those who want to help you.
Cases
While every person and family is unique, there are themes and experiences common on the giving journey which we know from our experience working with generous people and families, and from research in the field. Explore some of the ways we help others
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 Their 50-year-old family foundation had become inactive, its mission outdated and its board paralyzed by inter-generational conflict.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 guide the family through a revitalization process. She began with confidential interviews with each family member to understand their perspectives, and whether they shared a desire to fix what wasn’t working. A feedback session with the family affirmed their desire to move forward. 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.
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The Sterling Family Foundation was reborn. With a shared mission and a fair governance structure, interested family members re-engaged with enthusiasm. Granting resumed with a renewed sense of purpose, ensuring the family’s legacy of giving would continue, stronger and more unified than before.
Engineering a Young Family's Giving
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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.
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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.
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Sharilyn helped Jackson translate his intentions into action. They started by identifying the family’s core values, which centered on education and access to technology for underserved youth. To maximize simplicity and flexibility, Sharilyn recommended establishing a donor-advised fund (DAF). This allowed Jackson to make a tax-deductible contribution immediately while deciding on specific grants over time. Sharilyn then helped them create a "family giving" ritual. 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.
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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 family ritual has made philanthropy a tangible concept for his children. He feels confident he is building a meaningful legacy of generosity.
Launching a Legacy
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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.
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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.
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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 anchor for the family. Sharilyn led a family retreat where she helped them identify shared values and a vision for their giving as a family. This discussion allowed the children 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 included approaches to decision making. They also created a Giving Club for the grandchildren to learn about philanthropy through small grants.
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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
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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 as they have their own giving priorities.
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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.
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Sharilyn guided them through a structured process to help them focus their vision on two passions: early childhood literacy and workforce development. Next, she reviewed the pros and cons of 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.
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Jamil and Pearl now have an actionable roadmap for their legacy. 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
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A time-poor CEO with a deep commitment to promoting STEM education for girls.
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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.
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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.
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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.