For Vornado Realty Trust, AI is the new utility powering the way buildings run, deals get made, and work gets done. In this episode of the AI First Podcast, Box Chief Customer Officer Jon Herstein speaks Robert Entin, Executive Vice President and CIO at Vornado, one of the largest real estate investment trusts in the U.S. Robert shares how AI is helping Vornado transform everything from tenant experience to lease management, all while preserving the integrity of its iconic New York properties. From automating rent billing and managing 2 million invoices in the cloud to building AI-ready hubs for loan documents and lease abstracts, Vornado is putting intelligent content at the heart of how the business operates. Robert explains how they're pairing structured metadata with powerful AI tools to extract real-time insights, boost efficiency, and empower knowledge workers. If you're leading digital transformation, navigating content sprawl, or exploring how AI fits into your enterprise, this episode delivers a candid, deeply informed look at what it takes to lead with technology and make change stick. Key moments: (00:00) Reflecting on the early internet era and how AI is evolving differently (00:56) Introducing guest Robert Entin, EVP and CIO at Vornado Realty Trust (02:17) Robert’s background and Vornado’s transformation from legacy to AI-ready (03:35) How Vornado bet big on New York’s Penn District (05:15) From software engineer to CIO, Robert’s unique career path (06:35) Lessons learned transitioning from vendor to internal operator (08:52) The pace of innovation at Vornado and its leadership’s appetite for change (09:58) What “transforming real estate through technology” really means (11:02) From legacy systems to PropTech and smart buildings (13:15) Building converged networks to support modern building operations (15:07) Early move to cloud: why Vornado chose Box nearly a decade ago (17:25) Decommissioning legacy systems and modernizing file storage (19:27) How cloud content management laid the foundation for AI (20:56) Automating rent billing and invoice storage with Box (24:07) Migrating 2 million invoices from legacy to Box with metadata (25:21) Improving document search and retrieval with Box and Box AI (26:55) Enhancing tenant experience through the “Live Work Do” app (28:57) Measuring impact through tenant demand and amenity usage (30:57) Using Box AI to unlock insights from loans, financials, and earnings call data (33:03) Automating analyst summaries and accelerating knowledge work (35:03) The opportunity and challenge of AI for lease abstraction (38:10) Pairing structured metadata with LLMs for smarter lease insights (40:33) Challenges with early third-party AI tools and the promise of Box Hubs (42:07) Building advanced lease metadata templates with Box Apps and Extract (44:33) Why AI accuracy improves with better structured data (45:57) Educating execs on why focus and context matter for AI (47:34) Change management: finding “AI-ready” teams to build momentum (50:07) Lessons learned from system implementations and user adoption (52:11) How Robert evaluates when a solution is ready for rollout (54:05) Balancing business impact with end-user expectations (55:40) Managing sensitive data and using containerized AI models (58:10) AI’s role in reshaping knowledge work (01:00:06) Why business understanding matters more than just tech skills (01:02:20) Final advice for CIOs: use AI daily and learn how your business runs

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