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Mark speaks with Greg Nudelman, UX strategist, speaker, and author of UX for AI.

If you work in UX, product, or AI and feel like the ground is shifting under your feet, this is the kind of conversation that helps cut through the noise. Greg’s argument is simple but urgent: most AI projects are not failing because of the models. They are failing because teams are still choosing the wrong problems, using the wrong data, and applying outdated product habits to a completely different kind of technology.

This episode is worth listening to because it reframes where real value now sits for designers and product people. If your role has drifted into handoffs, surface level screens, or feature packaging, AI will expose that quickly. But if you can frame the right use case, understand customer pain, evaluate risk, and test fast with something real, your role becomes more valuable, not less. Greg brings sharp, practical thinking to what AI teams are still getting wrong and what UX and PMs need to do now to stay relevant.

In this episode, you’ll learn:

00:00 - The 85% Failure Rate: Why Enterprise AI Projects Keep Collapsing
05:21 - The Hadoop Syndrome: When Boards Demand AI Without a Strategy
07:32 - Robot Monkey Work: Have Designers Made Themselves Disposable?
12:56 - Horseman 1: Torpedoing Your AI Project with the Wrong Use Case
14:18 - Horseman 2: The Data Delusion and Building a Bullshit Generator
20:52 - Horseman 3: The Value Matrix and the Hidden Cost of AI Accuracy
22:28 - Horseman 4: Snowball Sprints and Killing the Traditional UX Handoff
26:44 - The Disruption of Product Management: Why AI Will Replace Bad PMs
32:24 - Becoming an AI MacGyver: Why Vibe Coding Beats Figma Prototypes
36:20 - The Six-Week Proof of Concept: Starting with Knowledge Management

Greg Nudelman

Greg is a UX strategist, speaker, and author focused on AI product design and strategy. Through UX for AI, he publishes frameworks, training, and certification for teams building AI powered products, with an emphasis on practical methods like Snowball Sprint, RAG refactoring, value matrix analysis, and agentic workflow design. His book, UX for AI: A Framework for Designing AI-Driven Products, was published in 2025.

Visit: http://uxforai.com

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UXI (UX Institute) Original Podcast 2026.
www.uxinstitute.com

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In this episode Mark speaks with Dan Winer, Director of Product Design at Kit, the creator focused email marketing and automation platform formerly known as ConvertKit. Dan brings a rare mix of design leadership, front end development experience, and deep B2B product thinking to a conversation that goes far beyond surface level AI hype.

This conversation starts with a familiar problem in SaaS: why so many products still feel bloated, fragmented, and harder to use as they mature. but goes deeper into how AI is reshaping design practice.

Dan argues that teams without strong UX foundations will struggle most because AI can accelerate delivery without improving direction. He also makes the case that design systems now need to be thought of differently. They are no longer just a bridge between design and engineering. Increasingly, they are part of how agents understand, generate, and build interfaces.

Mark and Dan also explore the changing role of designers inside modern product teams: when Figma still matters, where AI prototyping is already useful, why design engineers are becoming more important, and what design leaders now owe their teams in a fast changing landscape. Dan’s view is grounded but optimistic. Design is not disappearing, but the kind of designer companies will need may be changing fast.

In this episode, you’ll learn:

00:00 - Coming up on this episode with Dan Winer

03:31 - The SaaS Bloat Trap: Why Platforms Keep Getting More Confusing
04:19 - Enterprise Dictatorship: How High-Ticket Demands Quietly Ruin Self-Serve UX
07:05 - The Hardest Choice in Product Strategy: Deciding What NOT to Build
09:22 - Beyond the Wrapper: How Kit Actually Uses AI to Drive Creator Value Faster
13:27 - Workflow Over Hype: Defining What Makes AI Genuinely Valuable
14:18 - The Acceleration Trap: Why Weak UX Plus AI Equals Moving Faster in the Wrong Direction 00:15:58 - The Unsexy Reality: Why Deliverability and Trust Still Beat AI Trends
22:19 - From Months to Weeks: Speeding Up UX Research & Prototyping
30:50 - The Paradigm Shift: Why Design Systems Are Now for Agents, Not Just Humans
38:42 - The Leader’s Mandate: Preparing Design Teams for an Unpredictable Future

Dan Winer
Dan Winer is Director of Product Design at Kit, where he leads product design across a platform built for creators to grow their audiences, automate email workflows, and build sustainable businesses. His background spans graphic design, front end development, product design, and B2B software, giving him a practical perspective on how AI, UX, and product strategy are colliding inside modern SaaS teams.

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UXI (UX Institute) Original Podcast 2026.
www.uxinstitute.com

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Mark is joined by Luke Wroblewski, product leader, author and one of the clearest voices in interface design.

This conversation explores where interface design is heading as AI systems become more agentic, more capable, and more embedded in everyday workflows. Luke shares why he has long believed the goal is not better screens or cleaner layouts, but making the interface fade into the background so people can focus on what they are actually trying to achieve.

Luke explains how this shift is already happening. The prompt box may still be there, but the number of human inputs is starting to shrink as agents gather context, coordinate work, and pass information between systems. That changes the role of the person from direct operator to higher-level orchestrator, and it changes what good product design now needs to solve.

Mark and Luke also dig into the challenges this creates for UX and product teams. They discuss capability awareness, context awareness, and the overload of reasoning traces and system output that current AI products still push onto people. They also explore why designers need to get much closer to production, why static handoff culture is breaking down, and why this may be a golden age for people who genuinely love building products.

Fun Point: Mark recorded this conversation at 4 am!

What’s discussed in this episode:

00:00 - Introduction & The Future of Interfaces

02:30 - Dissolving the UI & Humanizing Technology

05:00 - The Shift to Agentic Workflows

09:12 - Object-Oriented Design vs. Pixel Manipulation

11:13 - Evolving Inputs: Less Typing, Voice, and Foot Pedals

13:54 - UI Trust & The "Pets vs. Cattle" Analogy

18:45 - The Three Core Challenges of Prompt Interfaces

23:20 - Context Awareness & Real-Time Sources of Truth

31:00 - The Evolving Role of Designers

36:40 - The Golden Age & Rapid-Fire Questions

Luke Wroblewski - https://www.lukew.com/
Luke Wroblewski is a product leader, author and long time voice in interface design. His work has consistently focused on making technology feel more human and reducing the friction between what people want to do and the systems they use to do it.

UXI (UX Institute) Original Podcast 2026.
www.uxinstitute.com

Support the show

UXI (UX Institute) Original Podcast 2026.
www.uxinstitute.com