Our Team

Jennifer Loving

With more than 25 years of experience in a variety of shelter, street and housing programs, Jennifer Loving has spent her career working to solve homelessness in Silicon Valley.

Since being tapped to lead Destination: Home in 2010, Jennifer has convened public officials, government agencies, private sector leaders, nonprofit executives and leaders with lived experience to implement a collective impact model to end and prevent homelessness in Santa Clara County, resulting in well over $2B in new public, private and philanthropic funding and over 28,000 people permanently off our streets since 2015.

Ray Bramson

Ray works systematically to meet Destination: Home’s goals by addressing key staffing, process, and infrastructure issues, while also overseeing the organization’s housing loan portfolio, grantmaking, and development functions. Having focused on homelessness and affordable housing issues for the majority of his career, Ray previously worked for the City of San Jose, leading the city’s Homelessness Interventions and Solutions Division for over five years.

Prior to joining the city, he was a philanthropy manager at Silicon Valley Community Foundation, and before that Ray worked with HomeFirst–a Santa Clara County safety net organization–as director of development. An alumnus of UC Santa Barbara, Ray spent the year following his graduation with the AmeriCorps National Civilian Community Corps serving impoverished communities throughout the southeastern United States. He is a senior fellow with American Leadership Forum Silicon Valley and a board member for Housing Matters, Veggielution, and Nonprofit Housing of Northern California (NPH). Ray is also currently pursuing his Masters in Liberal Arts from Stanford University.

Cassandra Benjamin

Cassandra has worked in the homelessness and affordable housing arena for more than 30 years – as a direct service provider, executive director, organizational capacity builder, and most often as a philanthropic funder.  Through her consulting firm, she develops and manages national grantmaking initiatives, facilitates learning communities, and supports cross-sector partnerships.  She has published numerous reports on philanthropy’s role in preventing and ending homelessness and increasing housing affordability and developed and implemented these grantmaking strategies for many foundations.  Most recently, she served as Interim Director of Affordable Housing & Homelessness at the Marin Community Foundation and the Project Director/Author of Growing Together: Advancing Housing Solutions for Workers in West Marin.  She earned her Master’s degree in Nonprofit Administration from the University of San Francisco; Bachelor’s degree from the University of Michigan; and is a graduate of Harvard Business School’s Executive Nonprofit Management Program.

Nathan Kano-Park

As the Senior Program Officer, Nathan Kano-Park supports a national targeted homelessness prevention initiative in reducing homelessness inflow nationally and building the federal case for prevention as a national strategy.

Nathan brings six-plus years of experience in the nonprofit and philanthropy sector, bridging direct service, community development, fundraising, and grantmaking operations. He previously supported fundraising and donor engagement at Sacred Heart Community Service, and served with Servant Partners, deepening his commitment to place-based, relationship-driven work in San Jose, CA. At Sobrato Philanthropies, he strengthened operational effectiveness for an economic mobility grantmaking team and provided strategic support for a $100M housing security initiative.

Nathan holds a B.A. from the University of Virginia in Global Security and Justice and American Studies (Race and Ethnicity). Based in Kāneʻohe, Hawaiʻi he’s motivated to see people and communities thrive wherever he is located.

Lydia Vainauskas

Lydia is a values-driven professional committed to advancing equitable, systems-level solutions to address structural inequities. As Senior Development Officer, she builds philanthropic partnerships and works closely with partners to secure the resources needed to expand homelessness prevention efforts.

Her background includes experience in institutional fundraising, donor stewardship, and grants management, grounded in a relationship-centered approach to advancing impact. Earlier in her career, she supported the distribution of COVID-19 Emergency Rental Assistance funding in Santa Clara County and worked as a special education teacher in Denver through Teach For America. She holds a Bachelor of Arts in Political Science and Music from Santa Clara University and is currently pursuing a Master of Public Administration at San José State University.

Fatima Burgos

As Senior Communications Officer, Fatima Burgos brings a deep commitment to advancing housing equity and ending homelessness. Growing up in the Bay Area as the proud daughter of Salvadoran immigrants, she uses her personal experiences and passion for amplifying the voices of marginalized communities as driving forces for her work. With a career focused on strategic communications, Fatima has contributed to initiatives addressing homelessness and the housing crisis through roles at local nonprofits including SV@Home and Downtown Streets Team. She is driven by the belief that those most impacted by the housing crisis should be at the center of the solutions.

Fatima holds a Bachelor’s Degree in Psychology and Race & Ethnic Studies from Barnard College, Columbia University.