Annie Reynolds

Annie’s work spans campaign planning and management, development assessments, case development, feasibility studies, and strategic operations… all with a focus on helping mission-driven institutions build the capacity they need to thrive. As Executive Vice President, she collaborates closely with CCS leadership and client partners to translate long-term goals into clear roadmaps, guiding institutions as they navigate periods of growth, transition, and opportunity.

Since joining CCS in 2014, Annie has led dozens of planning and campaign engagements, development assessments, case development projects, and custom learning initiatives. She spearheaded the launch and implementation of more than 100 feasibility and planning studies, an experience that continues to inform her approach to organizational readiness and philanthropic strategy.

Annie brings a balanced perspective that blends analytics with steady, relationship-centered leadership. Her work supports clients pursuing fundraising goals ranging from $1 million to $500 million across sectors spanning education, health, human services, arts and culture, and advocacy. She is valued for her ability to clarify complex challenges, structure teams for success, and design systems that support long-term impact.

Outside of her client partnerships, Annie contributes to the broader philanthropic ecosystem through her board and revenue committee service at The Ability Challenge. She holds a BA from Indiana University.

Annie lives in Chicago with her husband, David, and their daughter, Emilia. She is passionate about building inclusive communities and enjoys exploring the city’s cultural and neighborhood life.