Katherine Caskey

Director of Leadership Giving

Katherine’s work with philanthropic organizations spans over fifteen years in dedicated work in non-profit and educational leadership, major and corporate gift cultivation, and event management. She earned a BA in Spanish and Behavioral Science from Mount Mary University in Milwaukee, Wisconsin and has traveled and worked in Latin America, Europe, Chicago, and Southwest Florida.

In Florida, Katherine most recently served as the interim Chief Development Officer of The Greater Marco Family YMCA. At the Y Katherine focused on engaging new donors and led the team in successfully exceeding the annual fundraising goal to continue their mission in serving over 10,000 families and individuals living in East Naples, Marco, and Everglades City. Prior to the Marco YMCA, Katherine worked with Riley Philanthropy as a lead fundraising consultant to multiple Naples area non-profits. Before joining Riley, Katherine was the Vice President of Development for the Guadalupe Center of Immokalee, where she led her team to raise over $4 million a year in support of the Center’s 1,100 students. In Chicago, Katherine held tenure with Lexington College, a women’s college for hospitality management and led the integrated fundraising program. Prior to Lexington, Katherine was the trailblazer in the start-up of Cristo Rey St. Martin, an affordable, private, college-preparatory high school for students from low-income families. Upon completion of the feasibility study, she was instrumental in securing the 1.5-million-dollar start-up grant from the Cassin Educational Initiative Foundation and the Bill and Melinda Gates Foundation.
Katherine is mission driven and values giving back to the community. Katherine has served on numerous boards in Illinois, including the Coalición de Latinos Unidos de Lake County and the Junior League of Evanston-North Shore. She has received esteemed recognition from Lexington College for excellence in fundraising with the Ann Jans Front Runner Award and the Founder’s Award from the Junior League of Evanston-North Shore for outstanding service and dedication. In Florida, Katherine has held positions on the boards of the Association of Fundraising Professionals (AFP) as President-elect of the Collier-Lee Chapter, the Culinary and Hospitality Education Foundation (CHEF) as Vice President, and The League Club of Naples as VP of Development.
Katherine’s family has been in the Naples area for over 20 years. Katherine is passionate about Everglades restoration and enjoys spending time with her family and five-year-old daughter.