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

At American Humane Society, AI isn’t just about technology, it’s about saving lives and amplifying its mission.

In this episode of the AI First Podcast, Box Chief Customer Officer Jon Herstein speaks with Karthik Devarajan, Chief Technology Officer at American Humane Society, the nation's first humane organization dedicated to protecting animals for over 150 years. Karthik discusses how AI is transforming operations across American Humane Society's diverse programs, from disaster rescue to service dog training, enhancing their mission to protect animals at scale.

American Humane Society is using AI to modernize how it manages vast amounts of data across its programs, leveraging technology to identify patterns and assist with critical decision-making. Karthik shares insights into how AI is improving efficiency, including AI-assisted audits, image analysis from rescue operations, and reducing manual processes to save time for staff so they can focus on what truly matters - animal welfare.

Whether you're in the nonprofit space, technology, or operations leadership, you'll find valuable lessons in how to responsibly implement AI to amplify your mission.

Key moments:

(00:00) Introduction to American Humane Society’s 150-year mission
(02:04) Karthik’s role and scope of responsibility at American Humane Society

(05:23) Using AI to amplify animal welfare efforts through data analysis

(08:10) Innovation in a legacy organization

(10:00) AI’s impact on efficiency

(12:29) Applying AI to farm certification and rescue operations

(15:52) Building internal AI champions and fostering a culture of innovation

(18:47) Overcoming skepticism and demonstrating AI’s value through small wins

(20:29) Measuring AI’s impact on time savings and decision-making

(23:10) Using AI for enhanced audits and operational insights

(26:18) Rethinking data management and supporting AI adoption through collaboration

(30:43) How AI aligns with American Humane Society’s core values of compassion and trust

(34:02) Lessons learned from early AI pilots

(37:52) Scaling AI adoption and using technology to amplify kindness

(42:32) Advice for other nonprofits looking to integrate AI into their operations
(45:12) Managing AI risks through transparency and policy
(48:30) How to maintain trust with staff and stakeholders when adopting AI
(51:01) Key takeaways on balancing innovation with mission
(53:10) The importance of continual learning and iteration in AI adoption
(55:25) Preparing for future AI-driven initiatives in animal welfare
(58:10) Final thoughts on staying mission-driven while embracing AI technology
(59:50) Closing remarks and gratitude for AI’s role in advancing American Humane Society’s mission

AI is saving lives and Movember proves it.

In this episode of the AI First Podcast, Box Chief Customer Officer Jon Herstein chats with Graham Link, Chief Technology Officer at Movember, to explore how the organization is using AI to transform fundraising, operations, and global impact.

Movember is modernizing its 20-year-old fundraising platform with AI, accelerating development and improving quality while staying true to its mission and culture. Graham shares practical use cases like self-service employee support, the viral AI-powered mustache generator, and content hubs that connect staff across geographies to Movember’s rich knowledge base. Movember fosters safe AI experimentation through cross-functional governance, strong enablement, and a commitment to responsible innovation.

If you work in tech, nonprofit, or operations leadership, this episode offers a hands-on look at how AI can amplify your mission and scale your impact.

Key moments:
(00:00) Opening thoughts on culture and tough-but-fun projects
(01:22) The Movember mission and how tech supports global health initiatives
(03:07) Graham’s role and the scope of tech at Movember
(04:19) Why AI feels like a “career reset” for seasoned tech leaders
(06:32) How Movember uses AI for engineering efficiency and platform modernization
(08:44) Fun with AI: the mustache generator and supporter engagement
(09:43) Improving internal support with Box Hubs and content search
(12:29) Scaling knowledge access across global teams
(14:35) Exploring translation, SEO, and global content strategy
(15:52) Building a culture of digital transformation and experimentation
(18:47) Navigating change and enabling AI adoption across teams
(20:47) Movember’s cross-functional AI enablement framework
(25:56) Balancing innovation with data governance and cybersecurity
(28:35) Upskilling the workforce for AI literacy and effective prompting
(31:52) New roles in engineering and evolving responsibilities
(34:02) Leadership insights on adapting to rapid tech change
(36:37) A look inside Movember’s AI strategy lens
(39:34) Where AI belongs and doesn’t
(42:32) How Movember measures AI impact across quality and efficiency
(45:32) The power of seamless integrations and connected experiences
(48:01) Emerging AI use cases in fundraising and health initiatives
(50:33) Advice for CIOs and CTOs: frameworks, buy-in, and community learning

At Withum, AI is the catalyst for a new era of innovation and productivity.

In this episode of the AI First Podcast, Box Chief Customer Officer Jon Herstein sits down with Amel Edmond, Chief Information Officer at Withum, to explore how the accounting firm is leveraging AI to transform its internal processes and client services.

Amel discusses how Withum is leveraging AI to automate tax reporting, audit workflows, and administrative tasks, boosting productivity and accuracy while maintaining human expertise in decision-making. He shares the firm’s approach to overcoming AI adoption challenges, fostering innovation, and balancing AI with security, compliance, and trust.

Whether you're in IT, finance, or professional services, you’ll gain key insights on integrating AI into your workflow and its impact on efficiency and client satisfaction.

Key moments:
(00:00) Introduction to Amel Edmond and Withum
(03:15) AI’s role in transforming accounting and advisory services
(06:45) The journey of automating the 10-99 reporting process
(11:30) Case studies of AI use in auditing and reporting
(16:50) Overcoming resistance to change and fostering innovation
(22:00) The role of AI in driving client satisfaction and employee productivity
(28:20) Balancing AI adoption with regulatory compliance
(34:00) How AI can enable better business insights and decision-making
(39:40) The future of AI in professional services and its potential impacts on firm growth
(44:10) Closing thoughts on leadership and AI strategy in the modern workforce

AI is changing healthcare, and Stanford Medicine is leading the charge.

In this episode, Box Chief Customer Officer Jon Herstein sits down with Dr. Mike Pfeffer, Chief Information and Digital Officer, and Dr. Todd Ferris, Deputy CIO at Stanford School of Medicine, to explore how Stanford is deploying AI at scale, from ambient scribing in patient visits to automating workflows in clinical trials.

Mike and Todd share lessons learned from integrating AI into healthcare environments, the cultural shifts that made it possible, and how they ensure trust and safety in every AI implementation. They explain how Stanford’s unique “firm” framework helps prioritize high-value, mission-aligned AI projects that deliver measurable outcomes.

Whether you work in health IT, operations, or strategy, you’ll take away key insights on how to move from experimentation to enterprise-scale AI with confidence.

Key moments:
(00:00) Meet the leaders behind Stanford Medicine’s AI strategy
(04:01) Automation vs. augmentation in clinical care and research
(08:26) Rolling out ambient scribes across the organization
(13:31) Faculty-driven demand for AI innovation
(18:53) Digitizing analog workflows in clinical trials
(24:45) How Stanford sets AI priorities with its “firm” framework
(30:57) Balancing innovation with trust, safety, and governance
(43:00) Predictive care and precision medicine powered by AI
(52:45) The future of personalized healthcare at Stanford

Baylor University is pioneering the AI revolution in higher education, accelerating everything from report generation to reshaping the future of security.

In this episode, Jon Allen, CIO & CISO of Baylor University, joins Box Chief Customer Officer Jon Herstein to discuss how Baylor balances cybersecurity with AI adoption, from improving workflows to enhancing collaboration. He also explores the challenges of data privacy, security, and preparing students for an AI-first future.

You'll learn about the future of AI in content management, how it’s being used to improve operational efficiency, and how to build a culture that champions both innovation and responsible AI use.

Key moments:

(00:00) Jon Allen’s dual role at Baylor University

(03:10) Defining what it means to be AI-first at Baylor

(07:00) Real-world examples of AI transforming workflows

(12:30) Leveraging AI to enhance collaboration and speed up operations

(18:00) Balancing cybersecurity with AI adoption in higher education

(24:00) The importance of education and transparency in AI adoption

(30:00) Managing data privacy and security challenges with AI

(36:00) Preparing students for an AI-first workforce

(42:00) The future of AI in higher education and content management

(48:00) How Baylor is evolving to support AI-driven innovation

(54:00) Closing thoughts on AI adoption, culture, and strategy in education