Waterside alumni are a central part of our community. The School maintains relationships with each graduate, working with them through early adulthood to ensure all our alumni are empowered to become the leaders of tomorrow. Today’s Alumni Spotlight focuses on Caitlyn Rivera, Class of 2015! Currently, she is a sophomore at University of Virginia with the intention of majoring in Business. 

Caitlyn came to Waterside as a kindergarten student. She remembers her small class size and the teachers who provided a positive elementary experience with encouragement and an interactive learning environment. 

“I loved having such a small class size because everyone was really close with each other and it felt like a big family. I loved that Waterside was always a lively atmosphere, but also instilled a good work ethic and academic habits that allow me to thrive in my academics today.”

Caitlyn has been an active member of Waterside’s alumni community since she graduated from the School. For middle and high school,  she attended Sacred Heart Greenwich, and she participated in our College Boot Camp, which includes college essay workshops, SAT prep and information about financial aid. Today, she participates in the Alumni Careers Initiative (ACI) and Waterside’s College Success Fund. 

Last summer, Caitlyn interned at Altrinsic Global Advisors in Greenwich and Lexington Capital in New York City. She has already secured an internship at Fortress Investment Group LLC for the summer of 2024.  

“I am so grateful for this program,” Caitlyn said. “I have had the privilege of getting scholarships for my college tuition through Waterside, I’ve gotten three internships by participating in the ACI, and I’ve connected with many successful people with different backgrounds, who served as helpful mentors.”

Caitlyn Rivera interning at Lexington Capital with Luca Franzino ’14 (Caitlyn on right and Luca in center)

Since enrolling at UVA, Caitlyn is trying new things like Commercial Law––her favorite course so far. She also looks forward to beginning a tutoring program in Charlottesville that serves children in public school. 

“I’ve never studied law so it was really interesting to learn about something that directly correlated to my life like why I have the rights I do today,” Caitlyn said. “I find it interesting learning about how certain laws have developed based on the changes that are happening in society.” 

In addition to her academics, Caitlyn has joined UVA’s women’s crew team, now practicing five days a week. Her first regatta will be in Earlysville, VA on November 12 against Duke, Louisville Navy, University of North Carolina, and University of Minnesota. 

We are so proud of the success Caitlyn has achieved as a student and athlete; but we’re most proud that she continues to remain connected to Waterside as she grows.

“Waterside is a place of comfort,” she said. “A place I know I can always go back to––not only in times when I need guidance, but when times are good. I want to celebrate and share my successes with Waterside because I believe this School has set the foundation for a mindset to achieve greatness. From the first day of kindergarten, they were preparing us to lead and set a good example for those around us. This mindset has given me the ability to remain driven and dream big.”