Tessa Riley: Leading with heart

After spending more than a decade serving students, Assistant Principal Tessa Riley has become a leader who turns obstacles into opportunities. Riley’s  influence extends far beyond the walls of her office, often seen collaborating with faculty or engaging in campus activities. Since joining the administrative team, Riley brought in not only experience, but a commitment to creating a positive environment.

“Ms. Riley is a very compassionate, positive, proactive, and hands-on person. She has an incredible background with both counseling and leadership roles. She really does try her hardest to be her best self,” Middle College Counselor Rita Guerra said.

Before transitioning into leadership roles, she was a school counselor for almost seven years— six years and eleven months to be exact. She often credits the experience as the reason she was able to shift into administrative roles with ease. Before becoming an AP, Riley served as an academic dean at Del Lago Academy for eight years. Here, she focused on supporting the academic success of her students. However, when district budget cuts eliminated the Academic Dean position, she found herself stepping into the role of an Assistant Principal. While unexpected, she appreciated the opportunity to continue supporting students on their academic journey.

“While I don’t really love the discipline aspect of this job, I know it’s necessary. It’s the key to a successful school environment. My favorite part of being an AP is really what I was doing before— getting to know the students, figuring out what they need to be successful, and helping them achieve their goals,” Riley said. 

Despite her demanding schedule, she prioritizes forming connections with those on campus. She can often be found checking in on students or stopping by classrooms to offer her support. This active presence has made her a trusted figure for students and staff alike. She is described as a resource on campus—someone who will do everything in her power to support teachers and their students.

“Ms. Riley is someone that you can rely on. She’ll listen to you, give advice, and make sure you have everything you need to be successful,” Juliana Garcia, 12, said.

10 years ago, Riley’s family made the decision to leave Boston and move to California, a decision driven by her husband’s career in marketing. Having spent years working as a counselor and later a counseling director in Boston, she often reflects on her experience in the East Coast. Grateful for the lessons she learned there, she credits her direct supervisor at the time for shaping her leadership approach. While uprooting their lives and leaving the state was an unexpected step, she embraced the transition. Now, Riley is known for her transparency and integrity, two qualities she has picked up on in her years as a leader. 

“I have learned through a series of moments that if you promise you’re going to do something, you have to do it– you really have to be open and honest. Obviously there are certain things you can’t tell people, but it’s important to always be as honest as possible so that they know you’re trustworthy, ” Riley said.

Riley’s philosophy continues to guide her work as the designated Assistant Principal to the Middle College program. Middle College at Orange Glen is a partnership between EUHSD & Palomar College that offers students dual enrollment. As the only school in the district with this program, the environment for students and staff has been described as a bumpy road. Prior to Rileys administration, there were concerns regarding the change in courses each term and the needs of each student being met at the college. After dedicating over a year to the program, she has eased the concerns of staff, constantly advocating for students and managing discipline. Those in the program often emphasize their appreciation for Riley, who has been an integral addition to the team.

“Ms. Riley supports all of us. Whenever we need support with our students—whether it’s taking them on a field trip or finding resources for them— as an administrative leader, she works hard to make sure we have what is necessary. I would truly describe her as one of the best things to happen to our program, ” Guerra said.

For students in Middle College, Riley has been a key component in the success of securing essential resources for the program. Her hands-on approach has ensured that they have access to the materials and funding needed to succeed. For example, when students were unable to access textbooks for their classes at Palomar due to insufficient materials, Riley stepped in and spent time searching for each book.

“She’s been doing a lot for us, club-wise and program-wise. When she sees that students aren’t getting anywhere with the college campus, she’ll reach out and take control of the situation. She’ll do what she can to make sure we succeed,” Garcia, 12, said.

Beyond the four walls of her office, Riley’s unwavering presence at school events has made her stand out from other administrators. As one of the most involved figures at the school, she often embraces her energetic personality. Whether she knew it or not, while she was cheering on students at school events and participating in spirit weeks, she created an impression that made her friendly, approachable and “real” to the students she came in contact with.

“We have all these things we have to do. Some of which make life a little harder. So, I like to lean into the things that make life easier—more fun. More importantly, I do feel like I’m more connected to the kids when I participate in silly activities,” Riley said.

Her ability to effectively balance leadership with lightheartedness extends beyond the school campus. Despite spending a majority of her day in collaboration with administrators and students, she juggles the responsibilities of a mother with dedication. Those who know her well compliment her work to life balance, explaining that she works hard in both areas. 

“She has incredible energy! So, she can successfully play the role of a mother and an AP— she always fulfills her tasks 100 percent in both areas. Most times, even going above and beyond. Her kids are both little Mrs. Riley’s,” Assistant Principal David Mussatti said.

At home, Riley’s world revolves around her two children, Ben and Louisa, who get to see her in a way many do not. Regardless of the long hours of an administrator, she enjoys spending time with her family. Whether she is helping her children with homework or reminding them how much she loves them, she hopes to create special memories with them. Even at their young age—Ben is 8 and Louisa is 6—they both express their appreciation for their mom. 

“I love you and I want to be with you forever,” Ben said.