About Sharilyn

Dr. Sharilyn Hale is a trusted advisor in philanthropy who helps generous people, families and organizations give with passion, collaborate, and envision a meaningful legacy. Her bespoke advisory services help you explore questions of purpose and values – often at times of change or transition – so you can move forward with clarity and confidence.

  • While Sharilyn works with anyone wanting to make a positive impact, she specializes in supporting generous families through pivotal moments of transition, particularly as the rising generation prepares to lead. Whether their philanthropic tradition is new or long-established, she expertly blends corporate and family governance principles to help families define and build systems that support their vision for impact and make giving a fulfilling experience. She also brings this expertise as an advisor with Lansberg Gersick Advisors - global leaders in family continuity planning.

  • A respected educator and mentor, Sharilyn’s expertise is grounded in experience as well as academic rigour. Her doctoral research on governance and multi-generational family philanthropy produced a groundbreaking model for cohesive family giving. She is author of numerous articles and reports, including contributions to leading texts on the charitable sector and global philanthropy.  She holds additional degrees in Theology, Psychology, and Philanthropy.

  • Sharilyn is deeply committed to strengthening the philanthropy and family wealth ecosystems, within which she has spent her career. As a Chartered Director, she leads at the forefront of the field, engaged with organizations like 2164, the UHNW Institute, BoardSource, and P150, a global collaborative of philanthropy advisors. She serves on the Advisory Council for the Masters in Philanthropy and Nonprofit Leadership (MPNL) program at Carleton University, where she also teaches. Her past governance service has included the Toronto Public Library Foundation (in support of the world’s busiest library system), the Ontario Trillium Foundation, Canadian Feed the Children, and CFRE International.

  • In recognition of her significant career contributions, Sharilyn was awarded the King Charles III Coronation Medal in 2025. She also received a Family Wealth Report Award for her work advancing philanthropy in the Caribbean, where she grew up and continues to work.

Dr. Sharilyn Hale C.Dir
Founder & Principal

Who we work with

Watermark works with generous people and families who want a meaningful and impactful giving experience today, and perhaps for generations to come.  We have special expertise in supporting multi-generational families through pivotal moments of transition, particularly as the rising generation prepares to lead.

We happily collaborate with family offices, enterprise and wealth advisors, management consultants, and donor advised fund providers, recognizing we are all partners in the philanthropy ecosystem.

We are discrete about the individuals and families we work with, but select references are available to ensure your confidence.