Toni Tolentino Retires After 22 Years of Dedication to Windward

Toni Tolentino has always felt compelled to serve others, a mindset that has served her well in her 22 years at The Windward School. Ms. Tolentino credits her mother for instilling in her a strong work ethic and sparking her interest in facilities management. “My family was involved in real estate, and they owned personal properties as well. I found this type of work challenging and interesting,” she shared. 

Ms. Tolentino began her career in operations as a property manager of high-rise luxury apartments on Central Park South, working for a private family who owned the properties. It was during her 15-year tenure in this job that one of the owners, a medical doctor, shared an insight with her that impacted her entire world view. “I remember him telling me, ‘If you don’t follow up on things, especially if you’re a doctor, the patient could die.’ That stuck in my head all my life. I follow up. I have the memory of an elephant,” she laughed. “Sometimes I had to manage five to six things at once, which was never a problem for me.” 

After the family sold the properties, Ms. Tolentino moved on to work for Tiffany & Co., as Assistant Director of Facilities and Operations for their retail store and offices in Manhattan. She later moved on to Memorial Sloane Kettering in a similar position, and, finally, landed at NYU as Director of Facilities and Operations for about 15 years. 

Major life changes in the mid-1990s prompted Ms. Tolentino to consider relocating, so she began looking in Westchester for opportunities. She’d found that she enjoyed a school atmosphere and was fortunate to meet Stephen Littell, Assistant Head and Director of Finance and Operations at Windward at the time, whose responsibilities included facilities, maintenance, and operations. “Stephen wore a lot of hats!” she said. “I dropped off my resume and luckily he kept it. A few months later, he called me.” 

One aspect of Windward that stood out for Ms. Tolentino was the collegial atmosphere. She was struck by the fact that everyone on the team made it their business to help others. “Everyone cooperated with one another and was always willing to lend a helping hand,” she noted. Ms. Tolentino’s drive to serve others meshed well with the environment at Windward, as her colleagues attest; “She is very precise at her job, she pays attention to a lot of details. One other thing with Toni is that she’s always willing to help anybody in the entire school,” Administrative Assistant Mary Riddle-Armiento shared. “Toni is a no-nonsense person who gets the job done! Working with her over the last few years, I have experienced her strong work ethic and dedication to Windward. She takes pride in a job well done and creates relationships with outside companies that help her accomplish all the behind-the-scenes work for Windward.” 

In her retirement, Ms. Tolentino hopes to spend more time with her family. “I’m very close with my nephews,” she said. “I have been all my life. They are a tremendous part of my life.” Her family is also very involved in hockey, and she hopes to have more time to attend games. Wherever her path takes her, Ms. Tolentino knows that she wants to be of service to others. “Whether I’m retired or not, that is my make up. My personality is to help people as much as I can.”