Chief Advancement Officer

Cathleen Stone Island Outward Bound School is excited to announce that Jessica Thompson Somol will be joining the organization as its Chief Advancement Officer. She will begin her tenure on July 16, 2025.

Thompson Somol will oversee all fundraising endeavors, focusing on individual major gifts as well as securing support from foundations and corporate partners. Her notable expertise lies in revitalizing development teams and fostering engagement among donors and volunteers, propelling organizations to new heights. Thompson Somol brings a proven history of success, having led an impressive fundraising campaign at Charles River School that achieved over $10.8 million for a new middle school and endowment. Additionally, she is currently serving as the chair of the board and the development committee for a $25 million campaign for a new multi-arts center in MetroWest, where $19 million has already been raised.

Previously, Thompson Somol served as the Chief Development Officer for the Schwartz Center for Compassionate Healthcare. Her prior roles include Director of Development for Charles River School in Dover, Massachusetts, as Executive Director of Care 2 Communities (C2C), a global healthcare organization, and held roles in sales and marketing at Millennium Pharmaceuticals (now Takeda) in Cambridge, Massachusetts. Thompson Somol received a BA cum laude in Medical Anthropology from Harvard University and an MBA from The Wharton School.

Her long-standing commitment to social justice is reflected in her academic and professional journey, which includes studying in South Africa and working in rural West Virginia and Haiti. Through her work at Charles River School, she has observed the profound impact of hands-on, experiential learning, nurturing an environment where inquiry, self-agency, and outdoor exploration flourish. Thompson Somol demonstrates a strong commitment to advancing opportunity, equity, and systems change for young people and the adults who support them, and brings enthusiasm, passion, and a strategic mindset to her work.

This recruitment was led by Kennedy Kearney-Fischer with Karson Freeman and Rachel Banderob.