Caroline Day is Chief of Staff at Swim Digital Group, where she helps connect vision to action. She works closely with leadership and project teams to align strategy and operations and create structures that support both people and outcomes. Caroline is honored to work alongside Swim’s President and CEO, Trimeka Benjamin, supporting her vision and amplifying her leadership by translating strategies into effective, lasting impact. Known for balancing detail and big-picture thinking, Caroline helps colleagues move complex projects forward while mentoring and encouraging them to grow.
Before joining Swim, Caroline spent 13 years at Embry-Riddle Aeronautical University, where she advanced international education, graduate enrollment, and student experience initiatives. There, she held progressively senior leadership roles and gained expertise in admissions, communication strategy, program management, and student support. She managed admissions and onboarding for graduate and international students, coordinated orientations, and oversaw communications and programming that supported students from more than 140 countries. She also led strategic initiatives in communication and project management across the university, including the award-winning efforts that earned both the NAFSA Senator Paul Simon Award and the PIEoneer Award for international education. Her reputation at ERAU was built on clarity, dependability, and an ability to bring creativity to complex organizational challenges.
Caroline believes that, at its best, education helps to change generational poverty. Managing it well requires the same balance of care and precision that defines the hospitality industry: meeting individual needs while stewarding organizational resources. This philosophy guided her decision to pursue her Master of Science in Hospitality and Tourism Management at the Rosen College of Hospitality Management at the University of Central Florida. She holds a Doctor of Education in Higher Education Leadership from UCF and a Bachelor of Arts in English (Creative Writing) from the University of South Florida.
Beyond her professional life, Caroline is an ocean adventurer at heart, happiest when she’s experiencing the water along her native Florida coast. She finds joy in creative pursuits, including stitching, gardening, writing, and cooking. Looking ahead, she maintains that her “act two” will be just as fulfilling as her first, with dreams of opening an inn and writing. Guided by her personal mantra, “Have one, be one… a good Day,” she approaches both work and life with humor, creativity, and intention.
