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Alumni Feature: Tiffany Williamson Kelly reflects on why her daughter attends CSS

October 03, 2019

Alumna Tiffany Kelly '98 with her daughter Eva, who attends CSS.

For alumna Tiffany Williamson Kelly, The Colorado Springs School provided more than an education.

“It was like a second home. I loved all of my teachers. I loved being in small classes. I was known really well,” said Kelly ’98, a student from 6th through 12th grade. “It speaks volumes that my daughter goes here now.”

Her daughter, Eva, is a 1st grader who joined the school in prekindergarten after she and her family moved from Philadelphia. Eva sometimes asks her mother if she did the same activities at CSS that she does now.

“It makes me happy because my mom told me a bunch of fun stuff I could do — like paint pictures and things I could do in 6th grade,” Eva said while giggling during recess.

Kelly, who is director of alumni and family relations at Colorado College, is drawn to the smaller class settings at The Colorado Springs School because they allow for one-on-one instruction, among other benefits.

“One of the valuable pieces of CSS is it’s small enough that more than her two (classroom) teachers will know who she is,” she said. “Your child will be known, not just recognized.”

Kelly knows the CSS community not only as an alumna and parent but also as a staff member. She worked for two-and-half years as director of admission and financial aid, beginning in 2009. “Even as admission director, you notice all of the students and can tell when something is off,” she said.

She appreciates the co-curricular classes such as creative drama that 6-year-old Eva is offered at CSS because it’s a well-rounded approach to her child’s personality and development. It’s comforting to Kelly that some of the teachers she had and has known since she was 12, including Amy Johnson-Smith, are still at CSS.

Kelly was a member of the National Honor Society and head of the Spirit Committee who also played tennis, volleyball, and basketball. She remembers the tight-knit community and the social learning that helped shape her as a student. “I really had to learn to negotiate personalities. We were like brothers and sisters,” she said.

Alumna Tiffany Kelly '98 with her daughter at Carnival in September 2

She shares with her daughter her excitement about the overnight camping trips Eva will go on with her classmates.

“I love the outdoor education aspect that CSS emphasizes,” Kelly said. “It stretches you out of your comfort zone, and that’s what really challenges and changes students and why I want Eva to have that similar experience.”

In 2002, Kelly received a bachelor of arts in English language and literature from Wesleyan University in Middletown, Connecticut. After returning to Colorado Springs, she worked for The Broadmoor as an executive meetings manager and an assistant conference manager before returning to her alma mater in the admission office.

Kelly also received a master of education in human development and psychology from Harvard Graduate School of Education in 2012. She worked at the Agnes Irwin School, an all-girls college-preparatory school for prekindergarten through grade 12 in the greater Philadelphia area, where she was director of tuition assistance and special projects, as well as associate director of admission and tuition assistance.

When the family moved to Colorado Springs in 2018, Kelly’s husband, Shawn, had worked in independent schools, including as headmaster, for nearly three decades. They returned knowing where their daughter would attend school.

“It’s surreal, but it means a lot to be able to have Eva at CSS,” Kelly said. “It’s important to me. Walking back onto campus as a parent 20 years after graduating truly feels like a legacy story.”

This is part of an ongoing series focusing on CSS alumni whose children attend the school.

Alumna Tiffany Kelly '98 with her daughter Eva, who attends CSS.
Alumna Tiffany Kelly '98 with her daughter at Carnival in September 2