Kevin Cherry
Co-Founder, Inkwell Leadership Institute
Kevin Cherry is a seasoned financial and operational leader with more than two decades of experience across the education, healthcare, and nonprofit sectors. He currently serves at Upham’s Corner Health Center, where he oversees the organization’s financial health and operational management.
Throughout his career, Kevin has helped mission-driven institutions strengthen their financial foundations in order to better serve their communities. He previously served as Chief Financial Officer at Boston Renaissance Charter Public School, South End Community Health Center, and St. Mary’s High School in Lynn, Massachusetts, where he led financial strategy, operational planning, and organizational growth.
Deeply committed to community leadership and youth development, Kevin supports organizations including the John Shelburne Community Center and ArtsEmerson, and serves on the Board of Trustees at Clark University. He has also been recognized with induction into the Clark University Hall of Fame, the Boston College High School Hall of Fame, and the New England Basketball Hall of Fame.
Petrina Martin Cherry
Co-Founder, Inkwell Leadership Institute
Petrina Martin Cherry is a community leader and advocate dedicated to expanding opportunity for young people from historically excluded communities. As co-founder of the Inkwell Leadership Institute, she works to create pathways that connect high-potential youth with the mentorship, networks, and leadership experiences that can transform their futures.
Petrina helped envision the Institute as a national leadership pipeline rooted in cultural affirmation, wellness, and early-career exposure. Anchored by a transformative summer residency on Martha’s Vineyard, the program reflects her belief that young people thrive when they are surrounded by community, possibility, and leaders who see their potential.
Through her work with Inkwell, Petrina is committed to cultivating the next generation of leaders — young people equipped with the confidence, networks, and opportunities to shape their communities and drive lasting change.