Leaders in Housing: Anne Hollander of WinnCompanies

In Episode 3 of the Leaders in Housing series on AI Edge, Surface AI’s Wes Carrell sits down with Anne Hollander, VP of AI and Innovation at WinnCompanies, to talk about what it really takes to operationalize multifamily AI at scale, from governance and data orchestration to change management and property-level execution.

Episode Overview

This conversation goes beyond AI buzzwords and into the operational reality of making AI work inside a large multifamily organization. Anne walks through how WinnCompanies is building a foundation for multifamily AI that includes governance, data and tech orchestration, and team enablement, before chasing use cases. From protecting revenue, eliminating manual data entry, and streamlining compliance workflows to freeing teams from low-value tasks, this episode is a blueprint for bringing AI into property operations in a responsible, scalable way.

Key Topics Covered

• From pilots to portfolio-wide AI: How WinnCompanies moves from “cool pilot” to measurable, scalable impact across the portfolio.

• Building the AI foundation first: Governance, data orchestration, and enablement as prerequisites for any meaningful AI deployment.

• Protecting against revenue leakage: Where the immediate opportunities are in collections, certifications, onboarding, and document workflows.

• Eliminating manual data entry and silos: Using automation to handle repetitive, error-prone work so teams can focus on residents and assets.

• Driving human efficiency with generative AI: Practical ways staff use AI for emails, notes, transcripts, and admin tasks that add up to real time savings.

• Designing a pilot framework that actually scales: Visibility, clear success metrics, and “go/no-go” decisions rooted in NOI, cash flow, and employee impact.

• AI as augmentation, not replacement: Why the future of AI in housing is about freeing people to do higher-value work, not cutting heads.

• How AI will reshape organizations: The evolving role of leadership, talent, and culture in an AI-enabled property operations model.

About the Guest

Anne Hollander is the Vice President of AI and Innovation at WinnCompanies, one of the largest and most diversified residential real estate firms in the U.S. With a background spanning AI research, product innovation, and on-the-ground property management, Anne owns the strategy and execution of AI initiatives across the organization. Her remit: make the work work better, by using AI and automation to reduce revenue leakage, eliminate manual friction, and enable teams across operations, affordable housing, resident services, and beyond.

About the Series – Leaders in Housing

Leaders in Housing is a video series on by Surface AI, featuring real conversations with multifamily operators, asset managers, and technology leaders who are reshaping property operations with AI. Each episode goes beyond theory to focus on what’s actually working in the field, how teams are improving accuracy, strengthening governance, and using AI agents to drive measurable performance across their portfolios.