Fond Farewell to Stephen Littell After More Than 20 Years of Exceptional Service

Stephanie Huie

Director of Finance and Operations and Assistant Head of School

Mr. Littell is pictured on the left at the 2018 Benefit. 

Overwhelmingly touted by his colleagues as calm, cool, and collected regardless of the situation, Windward's Director of Finance and Operations and Assistant Head of School Stephen Littell shared that he wasn’t born with that particular skill set. Rather, he developed it over many years, nurturing opportunities to maintain perspective when circumstances made it difficult. "[In a previous position,] I hung the entire employee directory list on the wall of my office. When I ran into challenging situations, I would use that list as a visual reminder of all the people working hard to make the institution succeed. It helped me frame challenges within the grand scheme of things.” 

After receiving his MBA from the University of North Carolina at Chapel Hill, Mr. Littell began his career in hospital administration within a university setting, at the Department of Surgery at Duke University Medical Center. He gradually found himself drawn to the academic side of the job, and he realized that he could make a greater impact and be more fulfilled by a position that involved far fewer than 9,000+ employees. “I wanted to be involved in making decisions,” he noted. “In smaller settings, you do a lot of the work yourself, but you also get to influence a lot of the work.” 

“In smaller settings, you do a lot of the work yourself, but you also get to influence a lot of the work.” 

Mr. Littell transitioned to the K-12 market and spent more than twenty years working for independent schools in the NYC area. While he enjoyed working in smaller settings, he admitted to eventually feeling disenchanted by the atmosphere of privilege present in many private school environments. He decided to take a couple of months off to contemplate an alternate career path. “I wanted to stay in a place with a different focus, mission, and purpose,” he explained. It was during this hiatus that Windward’s CFO at the time, Karen Shafer, reached out to Mr. Littell to ask a favor. Having become acquainted as a fellow member of the Independent Schools Business Managers Association, Ms. Shafer was aware that he was available and was considering leaving the field of education. She asked if Mr. Littell could help out for a few weeks as Windward implemented a new all-school software program, Senior Systems.  

Drawn to the distinctive mission of the School, Mr. Littell was happy to offer his talents and assist Windward with the transition. He quickly realized that he thoroughly enjoyed the work, which was anchored by a mission and vision that deeply resonated with him, and offered the sense of fulfillment that he had been seeking. He happily accepted a permanent position when it became available. “When I started in the Business Office,” he shared, “people would call just to say, ‘Thank you. Windward has been so transformative for our child.’ It was gratifying, even eye-opening, to hear these messages, especially within the context of following up for tuition payments!”   

Mr. Littell’s profound engagement with Windward’s mission permeated his every action in his role as Director of Finance and Operations. It was this commitment that drove him as he successfully shephereded he school through its growth from one campus and 300 students to four campuses and 941 students. And it was this commitment that inspired him to conduct what he termed “a projection frenzy of accounting models” that addressed multiple possible scenarios for the School during the 2008-2009 financial crisis. Mr. Littell reflected, “During that time, things were so uncertain that no one knew what would happen if, for example, enrollment went down 30%. How would the School respond to parents who still needed to have their children here but couldn’t afford it as they could previously? All boats rise when the tides go up, but when things are bad you don’t know what’s going to happen.” His former colleague and friend Barbara Drayer added, "With the board, we called it The Good, The Bad, and the Ugly. Stephen did financial scenarios for all three of these situations.” Amazingly, “thanks to Stephen’s careful stewardship, Windward was able to move unscathed through the great recession of 2008-09,” Dr. John Russell, head of school at the time, noted. 

“Thanks to Stephen’s careful stewardship, Windward was able to move unscathed through the great recession of 2008-09.” —Dr. John Russell 

Further, it was with this commitment to Windward’s mission and vision that Mr. Littell approached the challenges related to the COVID-19 health crisis. His perspective was that facilitating in-person learning, for Windward’s unique community, was imperative: “A Windward education is not a luxury item—it’s an urgent, medical necessity that must be addressed immediately, even when the economic time is working against you.” Mr. Littell, partnering with the rest of the leadership team and the board of trustees, effectively balanced the need to “really open up the floodgates of cash” with the critical goal of maintaining the School’s financial stability. He continued, “We needed to upgrade facilities and systems, which we did, and we needed to make capital improvements.” The full support of the board of trustees highlighted the faith they had in Mr. Littell, as well, when they suggested spending what was necessary to open the 1275 Mamaroneck Avenue campus.  

Numerous colleagues at Windward enriched Mr. Littell’s experience during his time at the School. In particular, he noted that his relationship with the board members in general, and Treasurers, specifically, made a lasting impact: “Denis O’Leary, Ron Ongaro, Fred Chapey, Tom Flanagan, and especially current Treasurer Mark Ellman, have all been extraordinarily helpful and insightful over the years.” Mr. Littell also shared his respect and gratitude for Diana Glogau, Windward's Controller, for spearheading the modernization of the Business Office and its procedures.  

Head of School Jamie Williamson spoke glowingly of Mr. Littell’s tenure at The Windward School. “To say that Stephen has been steadfast in partnering with the organization to manage its finances doesn’t even do what he’s done justice. Stephen has been absolutely instrumental in helping us maintain financial success over the last 20+ years that he’s been at the helm. Stephen is a wonderful partner and a pragmatic problem solver.” 

Windward Board Treasurer Mark Ellman shared, “The image that comes to mind when I think of Stephen Littell is that of a dedicated, thoughtful champion of Windward who goes about his work with a calm elegance. His focus, attention to detail, and knowledge are a given. What hides beneath those great attributes is a passion for the mission of Windward, without which Windward could not have grown to its current stature.” 

As he moves on to retirement, Mr. Littell is looking forward to traveling to some of his favorite places—Sweden, France, and the Caribbean—as well as making room to explore other countries and cultures. Pursuing volunteer work is another goal, either with a local animal shelter or as a pro-bono consultant for a small, independent school. Ideally, he’ll seek an organization whose mission speaks to him as powerfully as Windward’s has, with the kind of interesting, diverse, and dynamic work that he came to love during his time at the School.