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