A Personalized Approach to Academic Support

Jennifer Hayman-Gross serves as the Director of Wellness and one of the school’s dedicated learning specialists, beginning her career as an academic support counselor for student athletes at George Washington University. Her professional philosophy is built on the principles of student-centered support, deep relationship-building, and a holistic approach that values both academic and emotional well-being.

Hayman-Gross’s approach is rooted in the belief that knowing each student individually and building relationships over time are essential for effective support. She implements a “looping” model, in which learning specialists follow students from sixth grade through graduation. This unique model enables specialists to truly understand a student’s journey—tracking their progress, identifying areas of growth and challenge, and providing consistent support throughout their KO career. “It gives us an opportunity and chance to get to know the student, their family, to be the keeper of their story, if you will, from an academic standpoint.” Through this continuity, Jennifer and her team become trusted partners for students and their families, fostering empathy, trust, and a sense of advocacy.  The team can see the progress the student has made over time, identify areas for growth, and understand what challenges may still be in the mix. 

Hayman-Gross leads an integrated team that encompasses all aspects of student life, including academic, emotional, and physical health. The wellness team includes learning specialists, counselors, nurses, deans, and, notably, the director of equity, inclusion, and belonging (DEIB). By welcoming diverse expertise and perspectives—especially through the lens of DEIB—Hayman-Gross ensures that all students feel a genuine sense of belonging and care. “We feel very strongly that a sense of belonging,” Hayman-Gross said, “ has everything to do with academic, physical, and emotional health.” The team collaborates closely to create supportive learning environments, develop individual support plans, and offer guidance to both teachers and families.

Hayman-Gross rejects a “one size fits all” approach. She and her team personalize plans based on a student’s strengths, challenges, and evolving goals. The school does not disclose diagnoses, but instead provides comprehensive and practical guidance for teachers, focusing on helping each student succeed. Communication with families is open, transparent, and respectful, with Hayman-Gross emphasizing the importance of partnership and ongoing dialogue. For various reasons, a parent may not be ready for their child to undergo an evaluation. “We are just opening a door to a conversation,” she said. “Having more information could be very helpful. Even if a child undergoes an assessment and shows no learning differences, there is still value in identifying the child’s strengths and leveraging them.

A key aspect of her philosophy is preparing students for successful transitions, particularly as they move from middle to upper school and, ultimately, from KO to college. In middle school, her focus is on developing fundamental skills, including organization, self-management, and familiarity with academic systems such as Google Classroom. As students advance, she emphasizes self-awareness and self-advocacy, empowering them to understand their learning styles and confidently communicate their needs so that it becomes intuition—essential skills that will serve them well in college and beyond.” We want our students to leave KO and be able to go to a college or university of their choice,” she said, “and have a strong sense of who they are as a learner, so they can meet with their professors and advocate for themselves, and understand what would be best for them in terms of best understanding college-level materials”

Hayman-Gross is keenly aware of the evolving role of technology and artificial intelligence in the education sector. She strives to remain one step ahead of trends, helping students discern between helpful tools and those that might limit authentic learning. “I think we’re in big trouble if we let AI lead the way,” she said. “We need to make sure that basic skills and critical thinking are embedded in the day-to-day life for students, and then they can decide how AI is going to supplement the work that their brain is going to do.” While she values digital resources like Quizlet, she also champions traditional methods—such as writing notes by hand—supported by research as effective for learning and retention. Her collaborative work with educators across Connecticut ensures she stays informed on current best practices.

Hayman-Gross relishes even the small wins in her job, which she says can have big implications. For instance, she might help a student develop a to-do list and then, over time, the student comes into her office with a to-do list they created on their own.”To see them self-actualize and to see them run that system themselves and that they have intuitively integrated some of the skills and strategies to be independent and to help them get from one day to the next is really satisfying,” she said.

Central to Hayman-Gross’s philosophy is the insight that emotion and mental health are foundational to academic achievement. She points out that anxiety can impede learning more than any specific learning difference, and so her team focuses on helping students manage stress and develop coping strategies. She encourages staff and new educators to exercise patience, celebrate small victories, and forge strong connections within the school community. “As an academic support person, you may not see progress or gains overnight or even in a quarter or a semester. All those small victories will add up and come together, leading to big gains. But it will happen,” she insists.

Hayman-Gross’s approach at Kingswood Oxford exemplifies the powerful impact of combining continuity, teamwork, personalized support, and a deep respect for each student’s unique journey. She ensures that our students are not only academically prepared but are also equipped with the self-awareness, resilience, and skills needed to thrive long after graduation.