Productside Stories

Season 4 Collection: The AI Product Manager’s Reality Check

Featured Guest:

Digvijay Singh (Senior Product Manager at YouTube), Aleks Bass (Chief Product Officer at Typeform), Roger Snyder (Principal Consultant and Trainer at Productside)
12/17/2025

What it actually takes to build AI-first products that work 

AI is everywhere. Confidence is optional. 

This curated Productside Stories collection brings together three unfiltered conversations with product leaders who are actually building AI-powered products at scale. Forget the buzzwords magic-wand thinking. We’re talking hard-earned lessons on judgment, culture, evals, agents, and accountability. So, do you think you’re “doing AI right”? This is your reality check. 

 

Episodes in this collection

 

Key Topics Discussed in This Collection 

AI Without the Hype 

Why “AI-first” doesn’t mean “AI everywhere,” and how strong PMs avoid shipping expensive experiments that look impressive but deliver very little value. 

Judgment Still Belongs to Humans 

From evals to agent guardrails, this collection shows why AI can accelerate thinking — but should never replace product judgment, accountability, or decision-making. 

Building AI That Actually Scales 

What it really takes to move from pilots to production: culture, procurement, metrics, experimentation, and the unglamorous work that separates momentum from mess. 

 

Why Listen to the Collection? 

In this thought-provoking episode, you’ll gain: 

  • A grounded view of what AI-first actually looks like inside real product orgs 
  • Clear mental models for agents, evals, and AI-powered workflows 
  • Practical leadership lessons from PMs building at YouTube, Typeform, and Productside 
  • Confidence to experiment with AI without outsourcing your thinking 

Start here to widen your perspective for AI in product as we head into to 2026. 

Related Resources 

Check out these additional tools and resources to sharpen your leadership edge: