As the Portland Public Schools enters into the 2026-27 school year, we have made a number of very exciting hires and moves to fill key leadership roles at the district and school levels. We are excited about the experience and energy that these team members will bring to our schools and students. For a detailed list of who’s who at the central and school leadership levels, including what their roles are, please visit the Central Office Staff and School Administration Directory on our website. Here are a few highlights of the leadership changes made over the summer:

• Dr. Abdullahi Ahmed has moved into the role of Assistant Superintendent for Student, Family, and Community Partnerships. Working in close partnership with Dr. Grace Valenzuela, Dr. Ahmed will draw on his gift for connecting people to strengthen community relationships and expand access to key programs like Make It Happen and Early College.
• Dr. Tremain Holloway is stepping into the role formerly held by Dr. Ahmed and will serve as the Assistant Superintendent of Secondary Schools. Dr. Holloway, who most recently was a strategic advisor to the superintendent of the Boston Public Schools, brings an impressive background in secondary leadership and a deep commitment to academic excellence and equity.
• Dr. Beverly Stevens has succeeded Dr. Angela Atkinson Duina (now serving as Superintendent of South Portland Public Schools) as our Assistant Superintendent of Elementary Schools. A trusted leader with 25 years of educational experience, including 17 years at PPS. Most recently, Dr. Stevens was principal of Ocean Avenue Elementary School, where she successfully guided Ocean Avenue to International Baccalaureate World School status.
• Stephen “Mack” MacKinnon has stepped into a new role as Director of Civil Rights Compliance. He has a background as both an educator (most recently at King Middle School) and attorney, positioning him well for this role.
• Jesse Applegate will be transitioning out of his role as Senior Director of Special Education by Thanksgiving. Over the next few months, he will work closely with Dr. Cheryl Proctor, Chief of Schools and Academics, to hand over leadership of this critical body of work to her.
• Caitlin Miller is now the Director of Secondary Special Education, after serving in a number of roles around the district, most recently bolstering the Deering High School administration team.

At the school level, the following leaders are stepping into new roles:

• Aris Ayala has moved from Lincoln Middle School to become Deering High School’s new principal.
• Ilunga Mutombo is Deering’s new assistant principal, transitioning from his school counselor role.
• Sarah Obare has taken over as Portland High School’s principal, succeeding Principal Sheila Jepson. She previously served as PHS's assistant principal.
• Heather Gilbert, most recently PHS’ culture and climate coordinator, will serve as PHS’ assistant principal.
• Blake Kastle has returned to Lincoln Middle School as its principal, having formerly served there as assistant principal from 2022 to 2025 and most recently as Director of Secondary Special Education.
• Alice Buckley is stepping into the role of interim principal at Moore, filling that position vacated by Principal Darralyn Jones, who recently decided to return to her home state of Michigan.
• Jim Moses, a respected retired administrator, is providing support to Moore on an interim basis to ensure a smooth transition as school opens.
• Jon Nauhaus has been appointed to serve as King Middle School’s interim principal for 2026-27, joining PPS with nearly two decades of middle-level leadership experience in Pennsylvania. Former principal Amy Marx has taken a new leadership position outside the district.
• Emily Parr is stepping up as interim principal of Ocean Avenue Elementary School for 2026-27. She is a longtime OAES educator who has been the school’s assistant principal since 2022.
• Hana Tallan will serve as the interim assistant principal at Ocean Avenue, having served in numerous roles across the district since 1996.
• Amanda Williams is Talbot Community School’s new principal, taking on the role held by Terry Young, who stepped down from that role at the end of the past school year. Ms. Williams comes to us from Providence, Rhode Island.