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

AI isn’t just improving property management,  it’s redefining how AMH serves 62,000 residents at scale.

In this episode, Philip Irby, CTO at AMH, joins Box Chief Customer Officer Jon Herstein live from BoxWorks 2025 to share how his team built a fully cloud-native platform to manage 62,000 single-family homes. He breaks down how AI drives leasing, maintenance, and communication and why success starts with a relentless focus on the resident.

From replacing legacy systems to deploying conversational AI for real-time support, Irby explains how AMH uses Box to manage unstructured content and scale personalized service across thousands of properties. Whether you're in proptech, operations, or enterprise IT, you’ll take away real lessons in modernizing platforms, integrating AI responsibly, and designing for end users.

Key moments:
(00:00) How AMH uses AI to scale resident experience
(03:15) Replacing legacy tools with Box as a single content platform
(07:30) ‘Let-yourself-in’ leasing and AI-powered customer journeys
(10:20) Meet “Amy”: The virtual agent handling 100% of inbound calls
(13:00) Automating maintenance intake with conversational AI
(17:30) Unifying structured and unstructured data with Box
(20:50) Using Box AI for contract reviews and HOA document search
(26:40) Advice on change management and AI adoption across teams
(30:00) Why discipline, not just technology, drives transformation

As AI continues to shape industries, Box is leading the charge with Intelligent Content Management, empowering businesses to work smarter and more securely.

In this episode, Ravi Malick, CIO at Box, joins Box Chief Customer Officer Jon Herstein to discuss how Box applies AI to optimize operations, enhance customer experiences, and drive innovation across the enterprise. Ravi also shares real-world examples of how AI is integrated into Box’s own workflows, like streamlining processes, automating tasks, and improving efficiency at scale.

Whether you’re in IT, HR, or another sector, you’ll learn how AI can be a game-changer for your business operations and how to integrate it into your organization for maximum impact.

Key moments:
(00:00) Ravi Malick’s path from CIO to leading AI innovation at Box
(03:10) Leveraging Box to enhance business processes
(07:00) Integrating Box with Salesforce and automating workflows
(10:15) AI-enhanced employee onboarding and faster ramp-up times
(13:40) Leveraging AI in legal contracts to manage metadata and risk
(23:45) Intelligent Content Management: How AI is transforming unstructured data
(36:45) Overcoming the challenges of AI sprawl and governance

As AI continues to revolutionize industries, Broadcom is at the forefront, using advanced AI tools to transform its operations and drive business growth.

In this episode, Stanley Toh, Head of Enterprise End-user Services and Experiences at Broadcom, joins Box Chief Customer Officer Jon Herstein to discuss how Broadcom is integrating AI across various functions. From customer support to employee experiences, they’re managing the challenges that come with AI adoption. 

Stanley shares how AI reshapes workflows, enhancing productivity and creating business value at scale. Whether you’re in IT, HR, or any other field, you’ll learn how to leverage AI to optimize operations and foster innovation.

Key moments:

(00:00) Broadcom's AI vision and Stanley Toh's role in driving innovation

(03:05) Why Broadcom is investing in AI and how it fits into business growth

(08:15) Broadcom’s governance framework for AI adoption

(13:45) Using AI to improve customer support and legal document management

(24:55) Addressing AI sprawl and balancing experimentation with risk management

(36:15) The importance of transparency and trust in AI applications

(41:20) The potential of AI in autonomous IT operations 

(45:40) Final thoughts on how CIOs can evaluate and implement AI tools effectively

With AI embedded into every aspect of its vast ecosystem, IBM is equipping its employees with powerful tools that enhance productivity, streamline workflows, and foster growth across the organization.

In this episode, Matt Lyteson, CIO of Technology Platform Transformation at IBM, joins Box Chief Customer Officer Jon Herstein to discuss how IBM is embracing AI to drive enterprise transformation. From enhancing everyday tasks to reimagining business workflows, Matt shares how they are integrating AI into every part of IBM's operations to empower over 280,000 employees to be more productive and efficient.

Key moments:
(00:00) Introduction to IBM's AI-first transformation

(07:30) Embedding AI into business operations and company culture

(15:00) Generative AI's role in automating business processes

(21:00) Scaling AI adoption and overcoming challenges

(27:30) IBM-Box collaboration: Integrating hybrid cloud and AI

(36:00) Improving user experience with AI-powered solutions

(50:30) Insights on AI, leadership, and the future of work at IBM

As AI rapidly reshapes financial services, LPL Financial isn’t just adapting. It’s leading the charge, equipping financial advisors with transformative, cutting-edge tools.

In this episode, Stephen Chien, Head of AI Advisor Solutions at LPL Financial, joins Box Chief Customer Officer Jon Herstein to discuss how LPL integrates AI into its advisor ecosystem. From saving time with AI tools, to fostering innovation at scale, Stephen shares insights on AI’s role in revolutionizing client service and business growth. Whether you’re in wealth management or any other sector, you’ll learn how to utilize AI to optimize operations, improve client interactions, and create a competitive advantage.

Key moments:
(00:00) The role of AI in wealth management and advisor empowerment
(03:12) How LPL Financial scales AI across its advisor network
(08:29) Leveraging AI for efficient client interactions and content management
(14:00) Ensuring compliance and data privacy in the age of AI
(18:52) How AI helps LPL advisors save time and boost productivity
(26:11) Challenges and opportunities of AI adoption in a regulated industry
(31:35) What’s next for LPL Financial

With generative AI reshaping industries, organizations face a pressing question: How do you power responsible and equitable adoption at scale?

In this episode, Kemal Badur, CTO of the University of Chicago, joins Box Chief Customer Officer Jon Herstein to share a pragmatic roadmap for integrating AI into a complex, decentralized academic institution. Explore what it takes to deliver secure, accessible, and impactful AI experiences, while respecting privacy, preserving intellectual property, and building trust across diverse stakeholders. Whether you’re in higher education or a global enterprise, you’ll gain firsthand insights on turning AI ambition into action.

Key moments to listen for:

(00:00) Why humility and transparency matter in AI leadership

(03:28) How to align AI with research, privacy, and academic values

(09:13) Building secure AI infrastructure with vendor partnerships

(13:08) Advice for scaling AI responsibly in a federated environment

(27:39) Why reliability matters more than creativity for agent-based AI

(31:22) What good governance looks like — without over-engineering

(43:31) Value, culture, and experience: defining success in AI transformation