After 15 years of dedicated service, Ham Clark resigned as headmaster and the Academy community welcomed Kolia O'Connor as the new head of school. Kolia brought 16 years of independent school experience as a teacher and an administrator.
The Academy opened its doors on the cusp of the Great Depression and the school was not immune to the national financial crisis. In 1933, Alexander C. Tener, Chairman of the Board of Trustees for Sewickley Academy at that time, wrote to all of the trustees asking each to underwrite $300 of the operating deficit for that year, so they could close the books and keep the school open.
In 2004, a strategic plan was developed that included input from 700 members of the Academy community. Centered on these strategic goals, the PICTURE THIS Campaign was launched in 2007 as the most ambitious fundraising effort in school history. The campaign, chaired by Nancy Means '72, Jeffrey Lenchner '77, and Amy Simmons Sebastian '80 added $15 million to the school's endowment - funding many innovative projects that enhanced the educational experience for all students.
In 1993, as a means of contributing to the Pittsburgh community, Sewickley Academy established its Summerbridge Pittsburgh program, a six-week, tuition-free academic enrichment program for middle and high school students facing limited opportunities.