Skip to main content
Mobile Menu Toggle

District welcomes new administrators

New chief financial officer begins in HPISD

Scott Drillette has been named Highland Park ISD Assistant Superintendent for Business Services
 
Scott Drilletee headshotScott Drillette comes to HPISD from Dallas ISD, where he served as Deputy Chief Financial Officer. He is the new Assistant Superintendent for Business Services and will be responsible for managing HPISD’s Business office, which includes the district’s budget, purchasing, payroll, food services and maintenance. In Dallas ISD, Drillette led six departments spanning budget, financial services, procurement, payroll, treasury services and risk management. He previously held similar roles in Dripping Springs, Manor and Brock ISDs.

“We are thrilled to welcome someone of Scott’s caliber to our business office operations,” Superintendent Dr. Tom Trigg said. “He brings to us a wealth of knowledge and experience in school district leadership that will be highly valuable to our community.”

An educator at heart, Drillette has nearly 20 years of experience in educational administration and leadership. He started his career in education as a high school math teacher and has since served as an assistant principal, principal, athletic director and director of payroll. Drillette has also spent eight years in the private sector as the general manager and CFO for a company in the waste and recycling industry.
 
“Highland Park ISD is truly a destination district known across the state for its tradition of excellence,” Drillette said. “I am very honored to be here and excited to get started. Thank you to the Board of Trustees, Dr. Trigg and the district leadership team for extending me this opportunity.”
 
Drillette earned a bachelor’s degree in Business Administration from Texas A&M University and a master’s degree in Educational Administration from Tarleton State University. His wife, Amy, with whom he has been married 30 years, is a reading and math specialist. Together, they have three children who have all pursued careers in public education.
 
He officially began his position as the new Assistant Superintendent of Business Services on Wednesday, replacing Mike White who accepted a similar position with Crandall ISD.
 
 

District welcomes new director of academic support

Ray Winkler has been named Highland Park ISD Director of Academic Support
 
Ray Winkler HeadshotRay Winkler, currently serving as the principal of Sloan Creek Intermediate School in Lovejoy, will join HPISD as Director of Academic Support. Winkler, who is in his 27th year in education and his eleventh at Lovejoy, has previously served as a middle school principal in Dallas and Little Elm, and assistant principal in Plano and Carrollton-Farmers Branch.

“It is so exciting to welcome an energetic educator like Ray to Highland Park ISD. Throughout his career, Ray has demonstrated a student-centered approach to campus and instructional leadership,” Assistant Superintendent of Education Services Lisa Wilson said. “He will be a tremendous addition to our Education Services team.”
 
Winkler’s career in education also includes experience as an associate high school principal, director of fine arts, director of summer programs and a classroom music teacher and orchestra director.
 
“I am thrilled to get the opportunity to serve the students, parents, and staff of Highland Park ISD. Highland Park is well-known across the country for its deep commitment to ensure that each child has an experience that is second to none, by design and not by chance,” Winkler said. “It is exciting to be a part of a mission-driven district that puts students’ needs at the center of every decision. The district and campus leaders here are amazing educators and people and I am looking forward to learning from each of them.”
 
Winkler earned a bachelor’s degree in Music Education and a master’s degree in Educational Administration. He will fill the position left vacant by Lydia Walden, who recently moved to a new role as Assistant Superintendent of Como-Pickton ISD.