Led by the best.

Deby Wolford

CEO & Executive Director

Over the past two decades, I have dedicated myself to building programs that create transformational changes to those who are served. This involved creating, designing and implementing programming including emergency shelters, transitional housing, affordable tax credit housing and permanent supportive housing programs. I have had the opportunity to create dynamic teams made up of compassionate staff that provided life changing services to chronically homeless individuals and families, single mothers with children, justice involved individuals and mothers reunifying with their children. 

By joining National Healthcare and Housing Advisors and launching Encompass Housing, I am so inspired by the opportunity to continue this transformational work on a national platform. 

Betty Medina

Director of Housing

Betty is a seasoned housing professional with over a decade and a half of experience in the affordable housing industry. She has supervised compliance for multifamily affordable housing properties across various states and has in-depth knowledge of many affordable housing program requirements, such as LIHTC, HOME, and HUD. She also brings extensive knowledge of affordable housing financing, real estate development, and property management. Her past supervisory experience also overseeing emergency, transitional, permanent supportive housing programs in the non-profit sector, makes her an invaluable addition to Encompass. She has a proven track record of delivering effective leadership and showing an aptitude for non-profit program management.

Along with being a nationally acclaimed Housing Credit Certified Professional, she holds a Master of Public Administration from Cal State University of Long Beach, and a Bachelor of Science in Human Services with a Minor in Psychology from Cal State University Fullerton.

She recognizes the importance of compliance in programs for Encompass’ ongoing growth, sustainability, and ability to continue serving the community’s most vulnerable populations.

John Simmons

Director of Data Analytics, Compliance & Training

John Simmons is an accomplished healthcare leader with a distinguished record of advancing operational excellence, regulatory compliance, and data-driven performance improvement within nonprofit and healthcare environments. As the former Director of Recuperative Care at Encompass Housing, he has demonstrated an exceptional ability to translate data insights into actionable strategies that enhance quality of care, streamline processes, and ensure adherence to organizational and state standards.

John’s professional foundation was built in the U.S. Army, where he served as a Combat Medic and Nurse. His military experience fostered a deep commitment to precision, accountability, and service—values that continue to define his leadership approach. Transitioning into civilian healthcare, John has held progressive roles spanning direct patient care, program development, and administrative leadership. His comprehensive understanding of both frontline operations and systemic healthcare challenges positions him uniquely to bridge the gap between data analytics and real-world impact.

Throughout his career, John has championed initiatives focused on compliance monitoring, performance evaluation, and staff development. He has led efforts to implement evidence-based training programs, strengthen data reporting systems, and align operational practices with trauma-informed and regulatory standards.

In his evolving leadership role, John is dedicated to building a culture of transparency, continuous learning, and measurable outcomes. As Director of Data Analytics, Compliance, and Training, he aims to leverage his analytical expertise, regulatory knowledge, and passion for service to drive organizational growth and sustain Encompass Housing’s mission of empowering the most vulnerable members of the community.

Jade Smith

Director of Recuperative Care & Interim Housing 

Jade Smith brings over 20 years of experience in social services and healthcare, leading with a servant’s heart and a deep commitment to compassion and collaboration. She believes in fostering a caring and supportive environment where individuals seeking care and stabilization can heal, grow, and rebuild their lives.

Before joining Encompass Housing , Jade spent a decade serving military communities—helping service members and their families access essential resources during the transition to civilian life. During that time, she also developed and led a veteran-specific mental health program, deepening her passion for mental health care and reinforcing her calling to serve others.

Throughout her career, Jade has supported diverse populations, including justice-involved individuals through partnerships with the Orange County Sheriff’s Department and collaborative court systems, those navigating substance use disorders, and women and children overcoming homelessness to achieve permanent housing.

Guided by both personal and professional experiences, Jade is known for her empathy, authenticity, and unwavering respect for the dignity of every person she serves. Her person-centered approach empowers individuals to find stability and create a path forward—one step at a time.

As the Director of Recuperative Care and Interim Housing, Jade is dedicated to effective leadership and exceptional client care. She is committed to advancing program outcomes, promoting client stabilization, and supporting successful transitions into permanent housing.

When she’s not working, Jade enjoys spending quality time with her family and friends and finding peace in nature whenever she can.

Kristin Jefferson

Director of Finance

Kristin Jefferson currently serves as the Director of Finance for Encompass Housing. She is a passionate and hard-working individual, and she has spent much of her life dedicated to the nonprofit community. She graduated from Clemson University with a degree in Financial Management with a minor in Accounting, and soon began her working career. She enjoys analyzing organizational finance and operations to offer insights. She has expertise in financial management, as well as project, portfolio, and program management analysis and evaluation. She also has a nuanced understanding of the operational and financial needs and challenges of nonprofit businesses.

Kristin has gained an insurmountable amount of experience through her work in the corporate and nonprofit sectors. She started at Prudential Health Care before moving into leadership roles at the Raise Foundation and 2-1-1 Orange County. During her time with 2-1-1 Orange County she managed the Point-in-Time Count, as well as the rollout of the Coordinated Entry System. More recently, she was a Consultant at Focus Strategies, a national consulting firm focused on reducing homelessness by leveraging the power of analytics and an equity informed systems approach. Kristin looks forward to contributing her broad finance and housing experience to the Encompass team and support their work to improve individual and community health and wellness.

Kristin is passionate about creating and fostering authentic, collaborative partnerships with colleagues. She thrives when having the latitude to identify opportunities, shape solutions, and improve outcomes.  In her free time, she enjoys visiting National Parks and traveling with her family, as well as spending time walking with her beloved dog. Kristin is excited to hit the ground running and contribute to the incredible and important work Encompass is doing in the community.