#shifthappens in the Digital Workplace Podcast

Hosted by Dux Raymond Sy

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Episodes

135

Latest episode

Aug 2026

Language

EN-US

About the show

#shifthappens is the podcast for leaders navigating the frontier of AI, security, and digital trust in the modern workplace. Hosted by Dux Raymond Sy, Chief Transformation Officer at AvePoint, each episode goes beyond the buzzwords to explore the real strategies, hard decisions, and lessons learned at the frontier of business transformation. Conversations span artificial intelligence, digital transformation, the future of work, information security, leadership, and real-world implementation — with guests who are actively shaping how enterprises adopt AI responsibly, defend against modern threats, and build trust at scale. Built for CEOs and business leaders, CISOs and security practitioners, technology decision makers, digital transformation leaders, and entrepreneurs. Ranked in the top 10% of podcasts globally by Listen Score, with 100% year-over-year listener growth and an audience spanning the Americas, EMEA, and Asia & Oceania. New episodes drop regularly. Subscribe and follow #shifthappens wherever you get your podcasts.

Listen to episodes

60 recent

September 10, 2026Episode 13629 min

Ep. 136: When the Patient Owns the Agent: The Case for Individual-First AI Governance

Healthcare organizations say patient data is secure. Paul Swider, CEO and Chief AI Officer of RealActivity, argues that security and patient control are not the same thing. In this episode, he explains why centralized healthcare systems remain attractive ransomware targets, why patients often have limited visibility into how their data is used, and why the next phase of AI governance starts when the patient owns the agent. He also explores why the 21st Century Cures Act has already redrawn the perimeter, and what that means for AI hasn't fully landed in most governance conversations yet. Paul walks through how he granted an AI agent access to his medical record, why a single-patient agent has a smaller attack surface than a centralized electronic health record (EHR) system, and why healthcare leaders should evaluate AI against today's care outcomes rather than on the expectation of perfection.

August 27, 2026Episode 13527 min

Ep. 135: Agents, Governance, and the Discipline Behind AI That Actually Ships

Moving AI into production requires clarity on what AI is allowed to do and who is accountable for the outcome. In Part 2 of our two-part series, Luise Freese returns to walk through how organizations can design AI agents with clear boundaries, embed governance directly into delivery, and build the operating model needed to scale. She also shares her 90-day approach for turning an early-stage proof-of-concept into a repeatable, production-ready capability.

August 20, 2026Episode 13429 min

Ep. 134: Escaping Proof-of-Concept Prison: The Path from AI Pilot to Production

Organizations aren't short on AI enthusiasm — they're short on the ability to turn that enthusiasm into anything that actually runs. In Part 1 of our two-part series, Luise Freese, developer, consultant, and author breaks down why so many AI initiatives stall after the demo. She covers how to evaluate use cases with intent, why data readiness shapes everything AI can deliver, and what leaders should be asking to turn early momentum into lasting operational capability.

August 6, 2026Episode 13335 min

Ep. 133: What Is Category Design? How to Stand Out in a Crowded Market

Most companies think they have a messaging problem. In reality, they haven't defined who they are and their place in the market. In this episode of #shifthappens, Mike Damphousse, co-founder of Category Design Advisors and co-author of The Category Creation Formula, breaks down why standing out goes beyond being better than the competition. When you own the category, the market doesn't compare you to others — it chooses you on your terms. He explains how category design moves beyond marketing into company-wide strategy, why AI alone won't differentiate your business, and how the most successful companies shape how the market thinks before competitors can.

July 16, 2026Episode 13227 min

Ep. 132: AI Attacks Move in Minutes. Can Your Response Keep Up?

GenAI has industrialized social engineering. The human entry point is now automated, personalized, and scalable, and that changes how security leaders must defend. In this #shifthappens episode, Andrew Carr, Managing Director and Global Head of Threat Management for Booz Allen Hamilton's Commercial Incident Response team, joins AvePoint Chief Brand Officer Dux Raymond Sy and AvePoint Chief Risk, Privacy, and Information Security Officer Dana Simberkoff to unpack what's genuinely new about AI-driven attacks — and what organizations need to do about it. Drawing on frontline incident response across healthcare, financial services, manufacturing, and more, Andrew explains why attackers no longer need to compromise systems to extract millions, why built-in trust is now a liability, and why the fundamentals that have been ignored for too long – zero trust, data classification, least privilege – are exactly what this moment demands. He also breaks down how AI should be used in defense: not as autopilot, but as a human-augmented layer that triages, prioritizes, and buys decision-makers the time they no longer have.

July 2, 2026Episode 13139 min

Ep. 131: AI Is a Tool, Not a Search Engine

Most organizations gave everyone access to AI — and then watched them use it as a search engine. In this episode of #shifthappens, Marco Galimberti, CEO of Venchi Asia Pacific, explains why the real shift is AI use. Drawing from his experience leading a global premium brand across manufacturing, retail, and consumer engagement, Marco breaks down where AI creates immediate value (process automation, pattern recognition, shift optimization) and where the longer-term opportunity lies: transforming how brands understand and respond to what customers actually want. The conversation covers why data overabundance is more dangerous than data scarcity, why AI currently works better in the hands of experienced professionals who can verify its outputs, why education systems need to prioritize fundamentals over tools, and why leaders who use AI openly and normalize it across their teams are the ones driving real adoption.

June 18, 2026Episode 13027 min

Ep. 130: AI Readiness Starts Before AI: Identity, Endpoints, and Security First

AI readiness doesn't start with AI; it starts with the infrastructure most organizations overlook. In this episode of #shifthappens, Lior Bela, Business Director for Microsoft Intune, breaks down what it actually takes to prepare managed service providers (MSPs) and their customers for AI adoption, and why skipping the foundation creates more risk than it solves. Lior explains why cloud-native environments are the prerequisite, not the afterthought, for AI success — comparing the journey to paving a road before driving a car on it. He discusses how legacy tooling and on-prem comfort create a growth ceiling, why AI agents should be governed with the same guardrails as employees, and what happens when organizations fail to offer sanctioned AI tools: shadow AI fills the gap. The conversation also covers the three-tier path to AI maturity, from baseline alignment to assisted automation to full autonomy, and why building trust in AI follows the same arc as trusting a driverless car. Lior closes with a practical 30-day action plan any MSP can follow: learn, experiment in a sandbox, and deploy on low-risk, high-impact processes.

June 11, 2026Episode 12935 min

Ep. 129: Where AI Meets Work: Why the Browser Is Becoming the New Work Surface

AI is reshaping how work gets done — but the deeper shift is where control sits. Increasingly, that control lives in the browser. In this episode of #shifthappens, Arunesh Chandra, Head of Product for Microsoft Edge for Business, breaks down how the browser has evolved into the environment where employees access information, interact with tools, and engage with AI. As this layer takes on greater responsibility, it brings control, visibility, and governance closer to the flow of work. That change is prompting organizations to rethink how oversight is applied within the systems employees use every day.

June 4, 2026Episode 12831 min

Ep. 128: Governance Makes AI Work in Healthcare: Managing Privacy and Security in Real Workflows

AI is already shaping how data in healthcare is accessed, exchanged, and used across clinical, operational, and development workflows. In this episode of #shifthappens, Kuma Partner and Executive Vice President of Privacy & Security Jenn Johnson explains why traditional governance approaches are being stretched — and where leaders need to respond differently. Drawing on real-world experience, Jenn outlines how established HIPAA foundations still matter, yet why AI forces organizations to rethink long‑held assumptions about consent, authorization, vendor risk, and data transparency.

May 28, 2026Episode 12733 min

Ep. 127: What AI Adoption Really Looks Like for Small Businesses

Most organizations treat AI adoption as a technology rollout. However, the ones gaining traction treat it as a leadership and culture challenge. In this episode of #shifthappens, Monica French, USA SMB Director at Microsoft, shares what she's hearing directly from small business leaders navigating AI — and why the human side of adoption is where most initiatives either accelerate or stall. Monica draws on frontline conversations with SMB founders, MSP partners, and her own career pivoting from traditional banking to fintech to explain why experiential learning outperforms passive training, why the chief human resource officer (CHRO) belongs at the AI table alongside the chief technology officer (CTO), and how lightweight governance can coexist with early experimentation. She also unpacks the gap between executive ambition and employee readiness — and what leaders can do to close it.