For DPS educator Raymond Simmons, an opportunity to grow as a leader became a chance to think more deeply about what DPS students need to feel supported and successful.

As Dean of Culture at Florida Pitt-Waller ECE-8 School, Raymond works closely with students and families every day. Through DPS Foundation’s Educators Take Flight program, he participated in the 4 Corners Latinx Leadership Academy, a year-long leadership seminar series that brings together Latinx education leaders from Colorado, Arizona, New Mexico and Utah to learn and grow together.
As we celebrate Hispanic Heritage Month, we’re highlighting how that experience has continued to shape Raymond’s approach to culturally responsive leadership at Florida Pitt-Waller.
For Raymond, learning alongside other education leaders reinforced the importance of understanding the individual experiences, backgrounds and needs students bring with them to school. “The conference reinforced for me the importance of leading with empathy, listening, and an equity mindset.”
Raymond also reflected on the type of school environment he wants to help create. “It also gave me the opportunity to reflect on my own leadership and think about how I can continue creating a school environment where every student feels valued, supported, and that they truly belong.”
One of the things that stood out most to Raymond was the community he found among the other leaders in his cohort. In an Educators Take Flight video earlier this year, he described “the strong sense of familia that consistently guided our work,” along with the connection, mutual support and shared purpose he found through the Leadership Academy.
Bringing lessons back to Florida Pitt-Waller
Raymond has also brought lessons from the 4 Corners Latinx Leadership Academy back to his day-to-day work with students and families. One of his biggest takeaways was the importance of looking beyond an immediate behavior or outcome and considering what a student may need in order to be successful.
At Florida Pitt-Waller, that mindset connects closely with work already happening through Multi-Tiered System of Supports (MTSS), attendance support and restorative practices, all part of the school’s efforts to understand and respond to the different needs of students.

“For example, when a student is struggling with attendance or behavior, rather than immediately focusing on consequences, I believe we have to understand the underlying barriers and determine what support the student and family need.”
Raymond pointed to transportation, family responsibilities and other challenges as examples of circumstances that can cause students to miss important learning time. Taking the time to understand those circumstances can help educators provide more meaningful support to students and families.
That perspective also connects to how Raymond thinks about equity in his everyday leadership. “The conference strengthened my commitment to making equity part of every day leadership. At Florida Pitt-Waller, that means continuing to build strong relationships with students and families, using restorative practices, strengthening MTSS, and making sure our systems are responsive to the different needs of our students.”
As Hispanic Heritage Month comes to a close, Raymond’s story highlights the importance of continued learning, connection and belonging in educator leadership. Through Educators Take Flight, DPS Foundation, in partnership with United Airlines, our official airline that makes the program possible, creates opportunities for DPS educators to strengthen their leadership, broaden their perspectives and bring new ideas and experiences back to their school communities. Raymond’s experience with the 4 Corners Latinx Leadership Academy is one example of how investing in educators can strengthen support for students and families in school and beyond.
Learn more about Educators Take Flight and how the program supports professional learning opportunities for DPS educators: dpsfoundation.org/what-we-support/educators/educators-take-flight/