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.

Ellen Meyer Joins The Children’s Guild Board of Directors

The Children’s Guild, a leading Mid-Atlantic nonprofit human-services and education organization is thrilled to announce the appointment of Holly Webb as the new Chief Human Resources Officer (CHRO). Holly brings over 20 years of experience in driving organizational success through strategic HR initiatives. As the Chief Human Resources Officer at The Children’s Guild, Holly will leverage her expertise to foster high-performance teams, enhance employee engagement, and maximize organizational efficiency.

Throughout her career, Holly has held key HR leadership positions for companies worldwide. Her accomplishments include designing and implementing service-oriented HR functions, creating metrics-driven processes, and leading workforce planning and development efforts that have resulted in significant cost savings and improved organizational performance.  Holly holds an MBA from the University of Indianapolis and a Bachelor of Science in Business from Indiana University’s Kelley School of Business.

“Holly Webb is a dynamic leader who embodies our core value ‘Our People Matter’,” said Jenny Livelli, President and CEO of The Children’s Guild. “We are looking forward to working closely with Holly to align HR strategies with organizational goals, promoting a culture of continuous improvement, and ensuring that our people and teams are optimally positioned to support our mission of transforming the lives of children and families.”

The Children’s Guild is also proud to announce the promotions of the following three prominent staff members:

Mark Rapaport is the new Vice President of Business Development: In his previous role as the Managing Director of Autism Services, Mark was instrumental in opening The Children’s Guild School – Transformation Academy located in Baltimore, MD. This facility serves students with autism and related disorders, providing a comprehensive and tailored educational experience. Mark’s leadership led to the successful implementation of innovative programs that improved student outcomes and satisfaction. In his new role as Vice President of Business Development, Mark will be working to expand current business lines as well as identify market growth opportunities and new business ventures to enhance The Children’s Guild’s service offerings.

Ronesha Estep-Franklin is the new Vice President of Program Operations: In her former role as Managing Director of School Operations, Ronesha Estep-Franklin oversaw the daily operations of our charter schools and preschool. Her leadership was pivotal in improving program operations, leading to enhanced educational experiences for students. Ronesha introduced several innovative practices that streamlined operations and boosted program efficiency. As Vice President of Program Operations, Ronesha will now oversee all program operations for The Children’s Guild, including nonpublic schools, charter schools, and preschools located in Maryland and Washington, DC, along with treatment foster care and behavioral health services, ensuring high-quality outcomes and program sustainability. 

Kelly Schwalbert is the new Vice President Chief of Staff: Having served as the Managing Director of Mission Advancement, Kelly Schwalbert was instrumental in building systems to improve operations across multiple departments. She developed and launched the first centralized grant department and expanded marketing services throughout the organization. Kelly’s strategic vision led to the creation and development of new departments, enhancing organizational capacity and efficiency. In her new role as Vice President Chief of Staff, Kelly will continue to support fundraising efforts while working closely with Jenny Livelli, President and CEO, as well as the Board of Directors and key stakeholders, to drive organizational strategy and growth.

In addition to these new staff positions, Ellen Meyer has been appointed to The Children’s Guild Board of Directors. Ellen is a Human Resources leader with over 36 years of comprehensive experience. She is a former teacher with a Bachelor of Arts in Child Development, and follows in the footsteps of her late mother, Louise Goldberg, who was also a reading teacher at The Children’s Guild and a former Board Member.  For two generations, the Meyer family has been a huge champion of The Children’s Guild. Their unwavering dedication and support have not only shaped the lives of children in need but have also woven a rich tapestry of love, commitment, and community spirit.

“A heartfelt congratulations to Mark, Ronesha and Kelly all who have been instrumental in building on the success of TCG and all who are well deserving of their new roles,” added Jenny Livelli. “We are also honored to welcome Ellen Meyer to our board, she and her family have built their legacy on compassion, service, and an unyielding belief in the power of education and care. I am excited for the future of our organization with such a dynamic leadership team in place.”

The Children’s Guild (TCG), founded in 1953, focuses on helping students and families find success socially, emotionally, educationally, and developmentally through special education, school-based mental health services, treatment foster care, autism services, family mental and behavioral health services, and workforce development programs.