Spotlight: Jenna Stewart (KY '24)

Kentucky Milken Educator Jenna Stewart (KY ‘24) is a fifth grade math teacher at Longbranch Elementary School in Union, KY. Stewart is passionate about student growth, preparing her students to be leaders in every area of their lives. Stewart received a 2024-25 Kentucky Milken Educator Award on December 11, 2024.

Milken Family Foundation: You’ve consistently achieved 90% student proficiency in math. What teaching strategies have been most effective in helping your students learn?

As a fifth grade educator, I’ve found that the most effective strategy for helping my students learn is building strong relationships and fostering a classroom community where everyone feels safe to be themselves, take risks and learn from one another. I strive to create a culture where we’re all in it together—where learning is fun, collaborative and supportive.

Mistakes are welcomed as part of the process, and I work hard to ensure students can learn from them without feeling embarrassed or discouraged. Flexibility is key! Meeting students where they’re at helps build their confidence and encourages growth. We use strategies like think-pair-share often, and I love giving students opportunities to lead the learning.

MFF: From coaching 'Girls on the Run' to leading the Lighthouse Leadership Team and hosting 'porch pop-ins,' how do these community-building efforts shape the culture of your classroom and support students as a whole person beyond academics? 

The various roles I’ve held at Longbranch have allowed me to build meaningful connections with students and families beyond my own classroom. These experiences have helped me grow in confidence and have provided opportunities to show students that I care about them as whole individuals. I believe school is about more than just academics, and I strive to ensure every student I encounter knows how valued and important they are in all aspects of who they are. For the students in my classroom, I make it a priority to show up for them beyond the school day. I attend sporting events, plays, dance recitals, and more. I even stay connected by attending some middle and high school events when I can. I do this to show them that I’ll always be there, cheering them on and supporting them throughout their journey in life.

MFF: How has your master's in school counseling impacted the way you approach education?

Finishing my master’s in school counseling has given me a new lens through which to view education. It has deepened my understanding of what students may be going through and how to better support their learning and emotional needs. Each child is unique, and we don’t always know the full story of their experiences. Students learn in different ways and experience a wide range of emotions. Viewing things from a counselor’s perspective has taught me so much and has especially helped me grow in patience and empathy.

MFF: How do you define “success” for yourself, and for your students? 

Success looks different for everyone as each individual creates their own goals in which they strive to achieve. These goals can be how to improve academically, professionally, socially or emotionally. 

MFF: How did you feel at your Milken Educator Award notification?

Speechless, shocked, and extremely loved would be some of the many feelings I had at my notification. Working in a building full of so many amazing educators, I couldn’t comprehend how or why I was the one who  was chosen. My students, coworkers, family and friends continued to make me feel so special the remainder of that day. It was certainly a time in my career that I will never forget. 

MFF: How have students responded since your Milken Educator Award surprise?

My students have been some of my biggest cheerleaders since the surprise. They have loved seeing all the media posts and continue to say that I’m now a celebrity. 

MFF: What drew you towards working in education?

From a young age, I’ve always had a passion for helping others, and teaching allows me to do that in so many unique ways every single day. I knew I wanted to work with children and be a part of making a difference in their lives. 

MFF: Who are your role models?

My parents have always been and will always be my greatest role models. They’ve pushed me to become the best version of myself, and they encourage me to follow my dreams. I truly wouldn’t be where I am today without their love and guidance. Both are incredibly hardworking, have enormous hearts and are always willing to help others. This is where my passion for helping others stems from. I aspire to be the kind of parent they are and hope to one day share the same deep connection with my own children that I’m so lucky to have with them now.

MFF: What do you hope students remember from their time with you?

I hope my students remember all the laughter and fun we shared together in the Stew Crew. I pray that when they look back, they know I cared about them as whole individuals and challenged them to always make someone smile. I hope they remember me not only for making learning fun, but also for helping them build the confidence to overcome obstacles and believe that the sky is the limit.