Monticello Central School District Assistant Superintendent for Business Lisa Failla has been named as a 2026 recipient of the Mid-Hudson School Study Council’s Excellence in Administration Award, in recognition of her leadership, financial stewardship and commitment to creating opportunities for students.
Ms. Failla brings 28 years of experience in public education and has served as Monticello’s Assistant Superintendent for Business since 2015. Her responsibilities extend beyond managing the district’s finances to overseeing a number of operations that help support student needs, including transportation, facilities, technology, and food service.
In nominating Ms. Failla, Superintendent of Schools Dr. Matthew Evans highlighted her ability to manage district resources responsibly while keeping students at the center of her decisions. He praised her work with the Board of Education, administrators, collective bargaining units and community members to identify ways to contain costs while preserving programs, services and employee benefits.
“She combines fiscal acumen with compassion, professionalism, and grace,” Evans wrote in his nomination letter.
Evans also cited consistently excellent district audits, responsible management of reserves and fund balances, and her leadership in long-term financial planning, capital improvements and labor negotiations.
Board of Education President Helen Jersey emphasized Ms. Failla’s thoughtful approach to navigating changing state funding, rising costs and other financial challenges while ensuring schools have the resources to support students and staff.
“She approaches every challenge with a positive attitude and focuses on finding solutions,” Ms. Jersey wrote in a letter supporting the nomination.
George L. Cooke Elementary School Principal Virginia Gallet, writing as president of the Monticello Administrators and Supervisors Unit, highlighted Ms. Failla’s collaborative approach to budgeting. She described how Ms. Failla works closely with principals and directors to balance school needs with fiscal responsibility and consideration for district taxpayers.
Ms. Gallet also praised Ms. Failla’s commitment to ensuring Monticello students have access to opportunities and experiences available to their peers in other communities, directing resources toward programs and services that support teaching and learning.
“Beyond her professional expertise, Lisa is known for her kindness, approachability, and a solution-oriented mindset,” Ms. Gallet wrote.
Ms. Failla will be presented with her award at the MHSSC’s banquet, which will be held on Oct. 29 at the Barn at Villa Venezia in Middletown.