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The Future of Affordable Housing: From Pen and Paper to AI

Thu Jun 25, 2026

Countdown Until webinar

The Future of Affordable Housing: From Pen and Paper to AI

A Webinar Exploring How Technology Is Reshaping Affordable Housing Operations

Thursday June 25 2026 @ 2:00 PM EDT

Presented By

Speakers and Panels

Trevor Samios

Trevor Samios

EVP, Operations Strategy & Solutions, WinnCompanies
Karen Esparza

Karen Esparza

SVP, Asset Management, BLDG Partners
Jelani Taylor

Jelani Taylor

Partnerships, EliseAI

Why You Should Attend This Webinar

Why This Matters

Affordable housing operators face more operational complexity than market-rate across every dimension — compliance, collections, maintenance, staffing — but a subset of portfolios are finding ways to outperform the market. EliseAI's latest webinar discusses that gap, identifies what the top performers are doing differently, and charts a course for the future of the affordable housing industry.

In this fireside chat, we're putting an operator and an owner in conversation about what high performance actually looks like in affordable housing today, and what goals they’re pushing towards moving forwards. Trevor Samios (EVP of Operations at Winn Companies, one of the nation's largest affordable operators) and Karen Esparza (SVP of Asset Management at BLDG Partners, an affordable housing owner) will share what they’re seeing on the ground, from collections recovery and staff retention to where technology fits into outcomes, and discuss what the future of affordable housing holds. Moderated by EliseAI's Jelani Taylor.

  • Operational complexity: Why affordable housing is structurally harder to operate than market-rate, and how manual, legacy systems and workflows are changing with the advent of AI tools
  • Staff retention: What happens when you take repetitive administrative work off the plates of site teams, and what it does for their job satisfaction levels
  • Collections: Overcoming the post-pandemic plateau in rent collection rates, and understanding what's actually moving the needle when it comes to securing asset performance
  • Resident services: How leading operators are using AI to deliver services residents actually need, including vocational training, legal support, and multilingual recertification, + how that impacts their outcomes
  • The owner's evolving expectations: What an affordable housing owner looks for in an operator today vs. five years ago 

 

Audience Value / Why Participate: This is a rare operator-plus-owner conversation grounded in real data. Attendees will hear two people with a working relationship speak candidly about the realities of affordable housing operations — staffing, compliance, collections — and where technology has actually delivered results vs. where the industry is still stuck, as well as where the industry is going. If you operate or own affordable housing, this is the conversation your teams are already having internally.

 

Agenda

Time Activity
2:00 PM
3:00 PM
The Future of Affordable Housing: From Pen and Paper to AI
Affordable housing operators are navigating growing operational complexity across staffing, compliance, collections and resident services, while owners are demanding stronger performance and accountability than ever before. This conversation brings together ownership and operations leaders to discuss where AI and automation are actually improving outcomes across affordable housing portfolios.