Ohlone's Bill Overton, Fairmeadow's Gary Prehn, the Adult School's Kara Rosenberg and Jordan Middle School Assistant Principal Ellie Slack all plan to step down in June.
Overton, who taught at Ohlone for 24 years before becoming principal in 2009, taught earlier at Sequoyah (now Palo Verde) and Green Gables elementary schools.
His work at Ohlone goes back to the earliest days of the school, which focuses particularly on integrating children's social-emotional needs into the curriculum.
"I'm considered a 'settler,' since I came in soon after the initial staff consortium and Board of Education decision," he said. "I did work with the 'pioneers,' though, some remarkable people, and even still keep in contact with some of them.
"I'm proudest of maintaining my energy and passion for kids and their school experiences and have always been proud to be part of PAUSD and this organization's tireless focus to do what's best for kids," Overton said.
Prehn, principal at Fairmeadow since 2011, previously served as principal at Escondido and Juana Briones elementary schools. Before moving to the administration, he taught at Escondido, El Carmelo and Loma Vista. He also taught English and social studies at Jordan Middle School.
"It has been such a unique and amazing journey, but I feel it is the right time in my career to close one chapter in my life and open another," Prehn said.
At the Adult School, Rosenberg oversees wide offerings of evening classes as well as the Preschool Family program and English as a Second Language. She first came to Preschool Family in 1978 as a parent with her 1-month-old son and was hired the following year. Before becoming Adult School's principal in 2000, she led a variety of programs, including ESL.
"It has been a pleasure to expand what we offer to the community and to work toward excellence in all of our programs," Rosenberg said. "I am proud of the teachers and the office staff, all of whom have made this happen."
Slack, herself a product of Palo Alto schools, had taught elsewhere for 25 years before returning to Palo Alto in 1994. She began her career in 1969 teaching math at Fremont High School. She later taught at La Canada High School, Los Angeles Baptist High School and Village Christian School for 19 years before her return to Palo Alto 20 years ago.
She taught math at Jordan and Palo Alto High School for 16 years before becoming assistant principal at Jordan in 2011.
"My favorite part of my career here was teaching mathematics to thousands of students," she said.
"The departure of these four outstanding leaders leaves a hole in our administration team," Superintendent Kevin Skelly said. "We are sad to see them go but wish them well on this new adventure. Their positive impact will be felt for years to come."
There was no immediate word on a search for replacements. Skelly announced last month that he himself will resign in June.