AI is scaling human expertise like never before.

In this episode of the AI First Podcast, Box Chief Customer Officer Jon Herstein sits down with E.A. Rockett, Adobe's Vice President and Legal CTO, to explore how AI is empowering experts across industries by providing the structure and tools to scale their knowledge. They discuss Adobe's unique approach to AI innovation, including the powerful "A-through-F" framework for evaluating AI use cases and the vital role of ethics in creating a trusted AI foundation.

Key moments:

(00:00) The best prompter for AI is AI itself

(00:34) Introduction to the AI First Podcast with Jon Herstein and E.A. Rockett

(02:14) E.A. Rockett explains his role and the concept of being a legal CTO

(03:23) Motivation behind blending legal expertise with AI innovation at Adobe

(04:23) Accelerating iteration and scaling AI to personalize solutions

(05:32) Adobe’s posture on AI innovation and balancing risks

(06:23) The journey with Firefly and creating safe, licensed models for customers

(07:15) Introduction of the A through F framework for AI governance

(09:01) Internal process for submitting AI use cases for evaluation

(10:09) Creating an enabling, not restrictive, environment for AI use

(11:33) Balancing creativity during hackathons with governance in AI use

(11:56) The role of ethics in Adobe's AI framework

(13:06) Ethics being integrated throughout AI projects, not just at the end

(14:20) Discussing where Adobe draws the line on AI use cases

(16:24) AI’s role in retaining talent and keeping employees engaged

(18:18) Attracting A players by providing access to cutting-edge AI technology

(21:06) The GIFTS framework: scaling expert knowledge through AI

(23:23) Using AI to create expert-level solutions even for non-experts

(29:36) Emerging hybrid roles due to AI, especially in legal and compliance fields

(32:33) Challenges in training junior employees while using AI

(34:06) Overcoming resistance in launching AI projects at Adobe

(42:39) AI unlocking scale in legal and compliance fields

(44:22) Filtering through AI to focus on relevant information

(46:47) Addressing AI risk and AI’s role in supporting human creativity

(50:14) Advice for CIOs and legal leaders behind on AI readiness

(53:30) Closing thoughts on the future of AI and its intersection with legal and tech

(59:04) How Adobe measures success of AI initiatives based on user engagement

The AI race isn’t about who starts first, it’s about who gets value fastest.

In this episode of the AI First Podcast, Box Chief Customer Officer Jon Herstein sits down with Box CIO Ravi Malick to zoom in on the biggest insights from a year of conversations with forward-thinking CIOs and technology leaders.

They reflect on what it really takes to move from AI hype to impact, from laying the groundwork with structured content and scalable governance, to building trust, navigating cultural resistance, and measuring value in a way your CFO will actually buy into.

You’ll hear sharp insights from guests across industries including real estate, healthcare, financial services, and higher ed, all focused on putting AI to work across content and knowledge workflows.

Key moments:

00:00) Why AI can’t replace human connection and why it shouldn’t
(01:26) Ravi Malick returns to recap the biggest lessons from 2025

(02:23) 2026 is the year to go from pilots to scalable AI

(03:29) 2025’s AI acceleration: funding, models, milestones

(04:29) The fragmentation of strengths across AI providers

(05:29) Consolidated content as the foundation for AI

(08:38) Unlocking unstructured data with metadata and governance

(10:13) Rethinking IT’s role: from gatekeeping to enabling innovation

(12:14) Why guardrails beat gates

(14:21) Shifting from top-down control to bottom-up experimentation

(17:01) Extensible governance models for fast-moving environments

(18:42) The importance of timing, agility, and building AI foundations

(19:32) Why sandboxes matter and how to balance freedom and safety
(20:55) Personal agents vs. hero apps - and what will win

(23:10) Empowering employees through education, not restrictions

(26:07) Cultural shifts: trust, experimentation, and collective learning

(27:31) Why change management is the hardest part of AI adoption

(29:31) Making AI feel like an unlock and not a threat

(31:19) How peer examples and storytelling drive real usage

(33:59) CIOs modeling behavior to build confidence in AI
(38:27) Choosing where not to use AI and keeping it human

(40:30) Measuring impact: outcomes > usage metrics

(41:48) Why ROI must be visible in the balance sheet

(44:05) Real-world impact: AI driving donations and business value

(45:22) Hard questions CIOs need to ask before scaling AI

(47:29) When custom AI platforms fall short and why
(48:21) Scaling what works: from experiments to enterprise-wide rollout

(49:33) Reengineering processes, not just automating tasks

(51:04) AI reliability: from 70% confidence to 90%+ precision

(52:25) The fast lane, the slow lane and how to choose your pace

(52:51) What’s next: AI that teaches you how to use it

(54:28) 2026 predictions: governance, commoditization, and agent adoption

(57:40) Audience Q&A: emotional intelligence in the AI age

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