Unsung Hero: Jennifer Cookston, Webb School of Knoxville

The Will J. Hancock Unsung Hero Award is given to business officers who have made extraordinary contributions to their schools and exemplify exceptional integrity, knowledge and motivation. At the end of each school year, new Unsung Heroes receive their award from their head of school, often at a significant school occasion such as a board meeting or an all-school ceremony. What makes these Unsung Heroes so special? The highlights below come straight from their colleagues' nominations. 

Stay tuned throughout the summer for additional profiles. See the full list of 2026 recipients.

Title: CFO
School: Webb School of Knoxville, Knoxville, TN
Years at School: 3

Superpower: Strategic Talent Architect. Jennifer Cookston led a comprehensive compensation study to ensure faculty and staff are competitively compensated and to establish the school’s first formal merit- and performance-based pay program.. The goal is to position Webb as a destination employer for top faculty and staff talent.

She has also “taken time and effort to develop her business office team to bolster their capacity in all areas of school finance and human resources,” said Webb School President Ansel Sanders. Together, these efforts are creating a strong foundation for attracting, retaining and rewarding high-quality talent across the organization.

Conditions Creator: Sanders described Cookston as “the ultimate conditions-creator, meaning that she creates the financial conditions to advance strategic priorities, work that more often than not goes unnoticed but is absolutely critical to the current and future states of the school.”

Examples of “condition creating”:

• Cookston created a dashboard to help identify trends and models for future budgetary processes.
• She increased the school's endowment draw to 4.5% to maximize operational impact.
• She led a tuition study that enabled the board to better understand and strategically leverage tuition revenue in support of institutional priorities. The effort also advanced transparency with both the parent community and faculty by clearly communicating financial decisions and the key levers that influence them.

Detail-Oriented: Cookston’s attention to detail is “unmatched, as evident by the school's clean audits, professionalized processes, and clear communication to parents and faculty,” reported Sanders. 

Other Duties as Assigned: Cookston leads the upper school’s student investment club — known as the Philanthropic Investment Group (PIG) — which engages more than 75 students in managing a real financial portfolio while supporting local charities and philanthropic initiatives. In addition, she frequently volunteers with the lower school.

Positive Force: Cookston “takes her responsibilities as CFO seriously, but she does not take herself too seriously, a leadership trait I admire and seek to embody,” said Sanders. “She knows how to laugh and how to build relationships across all aspects of the school. She always eager to improve, grow, and learn.”