The Children’s Guild has named Kelly Schwalbert Chief Strategy Officer and Organizational Effectiveness (CSO), effective July 1, 2026. The newly created role reports directly to President and CEO Jenny Livelli.

Kelly Schwalbert

The role brings integrated strategic leadership to TCG, with a clear growth mandate for the organization, built on systems and processes that make progress measurable and data-informed. 

Kelly was recruited to The Children’s Guild in 2020 as the Manager of Mission Advancement to help build the infrastructure behind big ideas. She has since grown into the Chief Strategy Officer role, earning each step through her work. Her strength is working alongside leaders to shape a vision for what’s possible, then building the structure, data, and intention behind it so that vision becomes something the organization can achieve. 

As Chief Strategy Officer, Kelly will lead organizational strategy, organizational effectiveness, strategic communications, board governance, continuous quality improvement, and admissions and enrollment strategy across TCG’s schools, clinical programs, and family services. She continues to serve as Corporate Board Secretary within her expanded scope. 

Kelly’s promotion reflects something we hold deeply at The Children’s Guild: that growth happens from within, and that our people deserve the chance to rise into roles worthy of their talent. Over the years, Kelly has led across multiple departments and consistently shown herself to be a trusted partner to me, to our Board of Directors, and to leaders throughout this organization. Her approach to leadership is teaching others, building capacity in the people around her rather than simply directing them. She has a rare gift for taking a vision and translating it into a clear strategy, then carrying that strategy all the way through to execution, always holding our organization to the highest standard of quality along the way. What has never wavered is her passion for serving our children and families, and that passion, paired with her ability to turn vision into results, makes her exactly the right person to lead our strategy and organizational effectiveness work as we move into this next chapter,” said Jenny Livelli, President and CEO of The Children’s Guild.

Programs/affiliates of The Children’s Guild include The Children’s Guild School of Baltimore, The Children’s Guild School of Prince George’s County, Monarch Academy public charter and contract schools, The Children’s Guild DC Public Charter School, The Outpatient Mental Health Clinic, Treatment Foster Care, The Children’s Guild–Transformation Academy, and Monarch Preschool College Park.

We are so glad to share this news with you: Rebecca Sinclair has joined TCGDC as our new principal this month. 

Ms. Sinclair’s first priority is to listen. She wants to hear directly from staff, families, and students about what they want to see and what they need. From there, her number one goal is simple. She wants every parent to know that their child is safe and loved here. That’s it. That’s the mission. 

She’s already told us what she wants the 2026-27 school year to be about: clarity, consistency, communication, and kindness. Four words, but they mean a lot, and we know she’ll bring them to life. 

Who is Ms. Sinclair? 

She brings nearly two decades of experience driving school culture, organizational transformation, and student-centered growth. She started as a classroom teacher and has worked her way through nearly every role a school has: teacher, Dean, Vice Principal, Director. She has walked in these shoes herself, so she knows exactly what students, families, and staff need. That kind of grounded, from-the-inside leadership is exactly what we were looking for. 

Most recently, she spent 10 years at KIPP DC, where she led compliance work across multiple campuses, making sure schools met enrollment, health, and regulatory standards. 

She has also spent years building up the people around her. Most recently, she led professional development for 100 teachers every year. She specializes in building data-driven instructional cycles and implementing Positive Behavioral Interventions and Supports (PBIS) frameworks. She has coached, mentored, and built strong teams throughout her career. 

Why Ms. Sinclair? 

Through TCG leadership’s listening tours with staff and parents, you told us clearly what you needed in a principal. You asked for someone who leads with authenticity and heart, who cares deeply about both students and staff, and who brings real structure and development into the program. Ms. Sinclair is that person. 

She also has deep roots in this city and in public charter school education. She and her family live in DC, and she is not coming here to learn what DC schools need. She comes with expertise and genuine love for the District and its people. As she puts it, she dedicates her life to her students, and she is happy to now have 200 children to call her own. 

Please join us in welcoming Ms. Sinclair to our school community. She’ll be at several school events over the next month and in the building regularly, and she can’t wait to get to know everyone.

Programs/affiliates of The Children’s Guild include The Children’s Guild School of Baltimore, The Children’s Guild School of Prince George’s County, Monarch Academy public charter and contract schools, The Children’s Guild DC Public Charter School, The Outpatient Mental Health Clinic, Treatment Foster Care, The Children’s Guild–Transformation Academy, and Monarch Preschool College Park.