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Affordable housing operations have grown dramatically more complex over the last five years. Compliance layers are multiplying, experienced staff are leaving, and resident needs have shifted in ways the pandemic accelerated (but didn't cause). Meanwhile, the tools most operators rely on were built for market rate and retrofitted (poorly) for affordable.
In this conversation, Trevor Samios, EVP of Operations Strategy & Solutions at WinnCompanies, one of the largest affordable operators in the country, and Karen Esparza, SVP of Asset Management at BLDG Partners, sat down with EliseAI's Jelani Taylor to talk about what's actually working, what isn't, and what the next five years need to look like. They discuss the real relationship between technology and process discipline, how the owner-operator dynamic is changing with real-time data, and how leading affordable housing teams are working to the industry's biggest gap—operational consistency at scale.
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Trevor Samios serves as Executive Vice President, Operations Strategy & Solutions at WinnCompanies, supporting operations, community partnerships and the advancement of mission-driven public policy on behalf of the organization’s real estate development and property management divisions. Samios began his career at WinnCompanies in 2017, launching Connected Communities as the resident services division of the organization before establishing the Connected Communities Foundation in 2024 to expand the scale and impact of its mission. He now serves as Chair of the Board of Directors, supporting Connected Communities’ staff and board leadership to grow its capacity, strategic partnerships, and collective-impact approach to community development nationally. Prior to joining WinnCompanies in 2017, Samios led the Community Impact team at Preservation of Affordable Housing (POAH) and operations for the Community Life team at The Community Builders (TCB), both national affordable housing non-profit organizations.
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Karen serves as Senior Vice President of Asset Management at BLDG Partners, a leading real estate investment firm focused on infill development and the preservation of workforce and affordable housing. She brings nearly two decades of experience in conventional and affordable multifamily real estate, contributing to the development and oversight of more than 14,000 residential units and over $1 billion in investment across the United States. In her current role, she manages a portfolio with $930 million in assets under management. Her leadership background includes key positions at BLDG Partners, Highridge Costa/ HCHP and Sequoia Equities.
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Jelani Taylor is an account executive at EliseAI, where he partners closely with affordable housing operators around the country on AI rollouts. A graduate of Cornell University, Jelani prides himself on working with the nation's largest owners and operators of affordable housing to deliver equitable, fair, and inclusive technological solutions that both empower affordable housing residents and protect asset performance.
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