Our Team

Together we Can Make a Difference

Leadership

Olivia Cherry, MBA
Co-Founder & Chief Operating Officer is a nonprofit executive and organizational leader with more than 20 years of experience building and scaling programs across workforce development, housing, youth services, education, and community-based systems.

As Co-Founder and Chief Operating Officer of Advancing Communities Together (ACT), Olivia leads organizational operations, strategic implementation, program development, compliance, workforce initiatives, housing services, and cross-sector partnerships. Her work has helped ACT expand from its early YouthBuild roots into a multi-program organization serving youth, adults, families, individuals experiencing homelessness, and justice-impacted communities throughout the Antelope Valley and Los Angeles County.

Olivia has extensive experience overseeing complex publicly funded programs and partnerships involving federal, state, county, and local agencies. Her leadership spans government contracting, workforce development, transitional and interim housing, homelessness services, career pathway programs, organizational systems, staff development, performance management, and operational compliance.

She has played a key role in the development and expansion of ACT’s housing and workforce portfolio, including transitional housing, interim housing, winter shelter operations, construction and skilled-trades training, career pathway programs, and industry-recognized certification initiatives. Her approach focuses on building strong operational systems while ensuring programs remain responsive to the people and communities they are designed to serve.

Before and alongside her executive leadership at ACT, Olivia spent more than a decade working within YouthBuild education and workforce systems, advancing from registrar and academic counselor to department chair and site coordinator. In that capacity, she supported multiple YouthBuild sites, strengthened student support systems, and helped align education, workforce preparation, case management, and community partnerships.

Olivia holds a Master of Business Administration (MBA) and a Bachelor of Arts in Business Administration from Southern New Hampshire University. Her leadership philosophy centers on turning strategy into execution, developing high-performing teams, strengthening organizational infrastructure, and creating sustainable systems that produce measurable community impact.

Today, Olivia continues to advance ACT’s mission while contributing to regional conversations around workforce development, housing stability, career pathways, systems transformation, and economic mobility.

Rossie D. Cherry, Chief Executive Officer and Co-Founder of Advancing Communities Together (ACT), launched ACT’s first core program, Antelope Valley YouthBuild, in 2007. Inspired by his personal challenges and upbringing in Pacoima, California, Mr. Cherry has spent the past 16 years providing direct and supportive services to youth and adults facing barriers such as poverty, incarceration, homelessness, and disabilities.

Drawing from his lived experiences, Mr. Cherry emphasizes education as a tool for empowerment and connection. His leadership extends to roles such as Chair of the Los Angeles Region YouthBuild Collaborative, Secretary of the National Directors Association for YouthBuild USA, Fellow of the California Department of Education’s Career Technical Education Program, and technical coach for YouthBuild USA under the Department of Labor.

Mr. Cherry also consults with grassroots organizations, cities, and agencies, focusing on capacity building, youth development, and transformational approaches to working with gangs and formerly incarcerated individuals.

Leadership begins with excellence and a servant's heart.

Leadership

Olivia Cherry

Rossie Cherry

Our Exceptional Staff Team

Construction Team

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