In this episode of Transform Work, John Winsor sits down with Melissa M. Reeve, Founder of Hyperadaptive Solutions, to explore what it takes to redesign organizations for the age of AI. Drawing on more than 25 years of leadership experience, including over a decade leading organizational transformation, Melissa shares why successful AI adoption requires more than new technology—it requires rethinking how work gets done.

The conversation explores AI-native organizations, organizational transformation, adaptive operating models, leadership, and practical strategies for creating lasting value with AI.

In this episode of Transform Work, John Winsor sits down with Iavor Bojinov, Professor of Business Administration at Harvard Business School and co-principal investigator of the AI and Data Science Operations Lab. Iavor’s work explores how AI, experimentation, and data science are reshaping decision-making inside organizations, combining academic research with practical experience from his time leading causal inference work at LinkedIn. This conversation offers a grounded look at how leaders can use AI and experimentation to make smarter, faster, and more effective business decisions.

Harvard Business School AI Institute

In this episode of Transform Work, John Winsor sits down with Raffaella Sadun, Professor of Business Administration at Harvard Business School and one of the leading researchers studying how management, technology, and work design drive productivity inside organizations.

Raffaella’s work sits at the intersection of economics, leadership, and the future of work. Drawing on large-scale data and real-world field experiments inside major companies, she explores how hybrid work is reshaping labor markets, how management practices influence performance at scale, and how generative AI is beginning to change the way teams collaborate and make decisions.

In this conversation, we dive into what actually drives productivity in modern organizations, how leaders should think about managing in a hybrid world, and why the real impact of AI may be less about automation and more about how work gets coordinated.

If you’re a business leader, HR executive, or anyone thinking about AI, workforce transformation, and the future of work, this episode offers a practical, research-backed perspective on what’s changing and what matters most.

Matt Beane is a professor at the University of California, Santa Barbara, and a Digital Fellow at Stanford and MIT. He is the author of The Skill Code , which draws on his original research into how people build skills while working alongside intelligent machines like AI and robotics. Matt is also the cofounder and CEO of SkillBench, a platform that transforms AI telemetry into actionable insights, helping executives guide organizational transformation while enabling knowledge workers to develop and adapt in real time.

In this episode of Transform Work, John Winsor sits down with Nick Bloom, Professor of Economics at Stanford University and one of the world’s leading researchers on remote work, hybrid work, and workplace productivity.

Nick is widely known for his data-driven research on how work is changing, from the rise of hybrid work models to the real impact of AI on jobs, productivity, and organizational design.

In a conversation often dominated by opinions, Nick brings evidence.

Together, they explore:

• How remote work has stabilized post-pandemic and why hybrid is becoming the dominant model
• What the data actually says about productivity, employee retention, and performance
• Why AI adoption is accelerating faster than any previous technology
• The real impact of AI on jobs, hiring, and career paths
• What leaders and organizations should be doing now to adapt

Drawing on large-scale research across thousands of firms and global executives, Nick breaks down what’s hype versus reality, and where the future of work is actually heading.

If you're a business leader, founder, or operator navigating remote work, hybrid teams, or AI transformation, this episode offers a clear, research-backed perspective on what matters most next.

Jay Singh, Founder and CEO of Casper Studios, joins the podcast to explore what it really takes to move AI from experimentation into production.

Casper Studios is an AI services firm that partners with organizations to design, build, and deploy AI systems that deliver measurable business impact. The company has supported clients across industries, including Netflix, Pepsi, hedge funds, private equity firms, and large healthcare providers, helping them operationalize AI and rethink how work gets done.

With a team drawing experience from LinkedIn, Microsoft, and Bain, and advisors connected to leading AI labs such as OpenAI and Anthropic, Casper Studios works across the full lifecycle of AI adoption, from discovery through deployment, while reshaping workflows and decision making along the way.

In this conversation, Jay shares his practical, outcome-driven perspective on AI implementation, what separates pilots from production systems, and how leaders can approach AI as an operational transformation rather than a technology experiment.

Note: this episode is best viewed on our YouTube channel, since our guest shares her screen several times to show some of the incredible art she's created with AI tools.

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In this episode, John Winsor sits down with Kelly Boesch, a visual artist and creative technologist working at the intersection of AI, design, film, and human expression.

Kelly has spent years exploring how emerging tools are reshaping the creative process. Rather than using AI as a shortcut, she approaches it as a collaborator that expands imagination, authorship, and creative range.

In this conversation, we explore what AI is changing about creative work, how artists can stay deeply human in an age of generative tools, and what this shift means for the future of creative professions.

If you care about the future of work, creativity, and human–machine collaboration, this episode is for you.

In this episode of Transform Work, host John Winsor sits down with Kyle Forrest, Principal at Deloitte and Deloitte’s U.S. Future of HR Leader, for a wide-ranging conversation on how AI is reshaping work, talent, and organizational design inside large enterprises.

Kyle shares what he’s hearing from CHROs and C-suite leaders as companies move from “AI pilots” to real production deployments, and why 2026 may become the year of measurable productivity gains. Together, John and Kyle explore how jobs are being unbundled into tasks and reassembled into new roles, projects, and workflows, including the rise of AI agents and what it means to manage “synthetic talent” alongside human teams.

Key themes include:

• The shift from one-time “change management” to continuous adaptation as AI capabilities evolve
• A practical framework for role evolution: AI-assisted, AI-augmented, and AI-powered work
• Why the real unlock is cross-functional: AI as a coordinating layer that breaks down silos and forces new operating models
• Who “owns the agent” inside organizations, and why many companies are forming centralized AI councils across HR, IT, Legal, and the business
• The overlooked force shaping the future of work: demographics, global labor supply shifts, and what that means for talent strategy

If you’re a leader thinking about the future of HR, workforce transformation, or the operating model changes required to compete in an AI-enabled world, this conversation offers clear frameworks, grounded insights, and a candid look at what’s coming next.

Listen now to hear why the future of work is not just about automation, but about redesigning how organizations run, how talent is deployed, and how humans stay empowered in the loop.