Founded in 2022, Osprey Strategy Group (OSG) seeks to provide evidence-based, concrete, actionable, and lucrative advice to nonprofits in New England and beyond. With a combined 30+ year career in nonprofits, Rebekah and Justin bring a wealth of knowledge and experience to any project.
We approach our work with the spirit of the Osprey, who does not wait for a fish to jump out of the water to grab it. We look forward to diving in with you to problem-solve, simplify, and strategize towards success.
Founder and Principal
Rebekah has a passion for forging powerful and productive connections between organizations and the people who can help them. With over 15 years in development and nonprofit leadership, Rebekah has raised more than $400,000,000, led high-performing teams, and created clear and comprehensive project-based and strategic plans.
Her experience spans mission-driven, grateful patient, and alumni-based fundraising and direct marketing. As Senior Director of Development and Community Relations at Sweetser, Rebekah combined and modernized the organization’s development and communications teams, leading to an 80% increase in funds raised in under 1 year. At Harvard University, Rebekah played a critical role on the team that closed a $375,000,000 gift from China and helped launch the Harvard Global Advisory Council. As Director of Development at Cummings School of Veterinary Medicine at Tufts University, Rebekah successfully led her team to increased success each year and served on the Dean’s Strategic Planning Steering Committee. Working for smaller nonprofits early in her career taught Rebekah how to capture the hearts of key partners, whether they be billionaires or neighborhood business owners.
Rebekah earned an A.B. from Bowdoin College, where she studied classical archaeology, as well as an M.Ed. from Harvard University focused on leadership and administration.
Justin currently serves as Executive Director of Full Plates, Full Potential (FPFP)–an organization combating child hunger in Maine–helping to set and execute organizational vision and strategy. Under his leadership, FPFP helped pass School Meals for all legislation in the state of Maine. He is a firm believer in the power and possibility that comes from combining potential with the spark of opportunity. He has spent his career working to dismantle broken systems and structures, in order to ensure that opportunity exists for all, and not just the privileged.
Justin attended Bowdoin College, earning an AB in Government and Teaching. He began his career with Harlem Children’s Zone in New York City where he found a passion for college access and completion work. This passion led him to Boston and Bottom Line, a national organization focused on supporting students from low-income backgrounds to, and through, college. He remained at Bottom Line for more than 11 years, holding a variety of roles including a four-year stint as Executive Director of the flagship Boston region. While in Boston, Justin completed the Institute for Nonprofit Practice’s certificate program through Tufts University and earned an MS in Nonprofit Management and Leadership from Northeastern University.