AI Won’t Save Your Roadmap: How Product Managers Stay in Charge with Roger Snyder 

AI is everywhere… including in your backlog, your boss’s OKRs, and probably your next performance review. In this episode, Rina sits down with Productside Principal Consultant and Trainer, Roger Snyder, to cut through the noise. They dig into what AI is actually good at, where it goes off the rails, and why product managers still own every decision. From vibe coding and Evals to agentic AI and ROI, Roger lays out a practical path for PMs who want to experiment without losing the plot. 

Key Topics Discussed in This Episode 

Key Topic #1 – AI as Your Assistant, Not Your Alibi 

Roger explains why AI is a thought partner, not a magic eight ball. He shares how strong critical thinking, clear prompts, and real accountability keep PMs in charge—even when AI is doing a lot of the grunt work. 

Key Topic #2 – Vibe Coding, Evals, and the ROI Problem 

From vibe coding to Evals, Roger breaks down how PMs should (and shouldn’t) use AI in discovery and delivery. He also tackles why so many AI investments slow teams down instead of speeding them up, and how to avoid “AI pixie dust” features. 

Key Topic #3 – Agents, Guardrails, and AI-First Orgs 

Rina and Roger unpack what “agentic AI” actually means, why not all “agents” are really agents, and how to balance autonomy with accountability. They also explore what AI-first companies get right about data, governance, and experimentation. 

Why Listen to This Episode? 

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

• A clear mental model for what AI can and cannot do for product managers. 

• Practical ways to use AI for discovery, research, and communication—without delegating your judgment. 

• A roadmap for when to use vibe coding, when to lean on Evals, and when good old-fashioned automation is enough. 

• A simple way to spot real agent use cases vs. costly “because AI” experiments that blow up budgets and erode trust. 

  
  

You’ll walk away with a healthier mix of AI optimism and skepticism—and a challenge from Roger to experiment with AI every day in 2026. 

Related Resources 

Check out these additional tools and resources to add to your PM belt: 

• Productside Resource Library 

• More Productside Stories Podcast Episodes 

• Explore Productside Courses 

Leading Product Work in a World Where Failure Isn’t an Option 

When your “product” is clean drinking water, the margin for error is… basically zero. In this episode, Portland Water Bureau Interim Director Quisha Light takes us inside the realities of leading innovation in a space defined by public trust, mission-driven work, slow-moving systems, and life-or-death stakes. From navigating union constraints to modernizing customer service to preventing $14K leak disasters, Quisha reveals what it really takes to move a legacy public organization forward — without breaking what people rely on most.   

Key Topics Discussed in This Episode 

1. Innovating when you can’t just “move fast and break things” 

Quisha explains why public-sector work requires careful experimentation, meticulous community engagement, and a deep understanding of real human consequences.   

2. Building a product culture inside government constraints 

From union rules to multi-month approvals to city council hearings, Quisha breaks down how she rebuilt a learning culture and empowered teams to try small bets responsibly.   

3. Customer obsession when “customers” = your entire city 

How she reframed Portland’s water services around accessibility, self-service, data-driven decisions, and a singular mission: keep families safe, supported, and never in the dark.   

Why Listen to This Episode? 

In this powerful conversation, you’ll learn how to: 

• Turn product principles into public-good impact — even when your org moves at government speed 

• Build innovation into legacy systems without risking public trust 

• Lead mission-driven teams who genuinely care about the community 

• Design services for vulnerable customers with dignity, empathy, and real-world awareness 

• Reignite purpose when product work starts feeling disconnected from impact 

If you’ve ever wondered what product leadership looks like when your “users” are literally everyone, this episode is your blueprint.  

Related Resources 

Check out these additional tools and resources to add to your PM belt: 

• Productside Resource Library 

• More Productside Stories Podcast Episodes 

• Explore Productside Courses 

How to Find Product-Market Fit (Without Fooling Yourself) 

Founders love to sprint. Markets prefer you walk, listen, and maybe ask a few humans what they actually want. In this episode, product leader and startup advisor Shweta Agrawal joins Rina to break down why so many early-stage teams skip the fundamentals  (customer discovery, focus, ICP clarity) and pay the price later. From health-tech to ed-tech to “AI for everyone” tools, Shweta shares raw stories, red flags, and the simple practices that separate wishful thinking from real traction. 

Key Topics Discussed in This Episode 

Why Listen to This Episode? 

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

• A reality check on the biggest founder blind spots (and how to avoid them). 

• A practical walkthrough of PMF signals that aren’t vanity metrics. 

• A step-by-step look at launching intentionally — not reactively. 

• Lessons on adapting your product for different regions, cultures, and buying habits. 

  
  

Whether you’re a PM or a founder, this episode will recalibrate your instincts and help you build with confidence, not guesswork.  

Related Resources 

Check out these additional tools and resources to add to your PM belt: 

• Productside Resource Library 

• More Productside Stories Podcast Episodes 

• Explore Productside Courses 

From Best Buy to Oldcastle: How Jennifer Sabetti Built a Career on Customer-Centric Leadership 

Early in her career, Jennifer Sabetti learned a simple truth at Best Buy: “Have fun while being the best.” Today, as VP of Product Strategy at Oldcastle Infrastructure, that mindset shapes how she leads teams, hires talent, and mentors the next generation of PMs. In this episode of Trailblazing Women in Product Management, Jennifer joins host Nicole Tieche to share how retail taught her to love the customer, embrace change, and build teams that thrive on curiosity and culture. 

Key Topics Discussed in This Episode 

Core values that never expire 
How “learning from challenge and change” became Jennifer’s lifelong leadership principle.Key topic #2 

Transitioning across industries 
Why focusing on customer value makes any career pivot possible. 

Mentorship and team growth 
The overlooked art of spotting (and becoming) a great mentor at work. 

Why Listen to This Episode? 

In this refreshing and candid conversation, you’ll learn: 

• Why your first job might teach you your most important leadership lessons. 

• How to build resilient, high-performing teams in complex product environments. 

• What hiring for passion (not just skills) really looks like. 

• How to find mentorship moments in everyday interactions. 

Jennifer’s story is proof that customer-centric leadership transcends industries — and that positivity is a powerful career strategy. 

Related Resources 

Check out these additional tools and resources to add to your PM belt: 

• Productside Resource Library 

• More Productside Stories Podcast Episodes 

• Explore Productside Courses 

From Layoff to Launch: Building an AI Businessfrom the Ground Up with Cooper Craig

When a product manager loses his job, what happens next? For Cooper Craig, it meant building his own AI automation agencyfrom scratch. In this episode, he shares how grit, community, and product thinking helped him rebuild—turning job loss into a thriving business. From building voice agents that actually sound human to managing growth without funding, Cooper’s story is the blueprint for every PM who’s ever asked, “What’snext?”

Key Topics Discussed in This Episode

1. The PM to Founder Leap:
How Cooper turned a layoff into a launchpad by applying product management frameworks to entrepreneurship.

2. Building Voice AI That Doesn’t Sound Like a Robot:
The art (and headaches) of designing conversational AI that’s actually human.

3. Product Thinking as a Superpower:
Why being a PM made him better at pitching, prioritizing, and delivering value—client by client.

Why Listen to This Episode?

In this refreshingly honest conversation, you’ll gain:

• A real look at what it takes to rebuild after a layoff.
• Frameworks to apply PM thinking to entrepreneurship.
• Lessons on balancing AI innovation with boundaries (and burnout).
• A reminder that humility and hustle can be your biggest assets.

Because every PM secretly dreams of building something of their own—Cooper just did it first.

Related Resources

Check out these additional tools and resources to add to your PM belt:

• Productside Resource Library
• More Productside Stories Podcast Episodes
• Explore Productside Courses

Building an AI-First Organization the Typeform Way with Aleks Bass 

What does “becoming AI-first” actually look like inside a real company? Aleks Bass, Chief Product Officer (and interim CPTO) at Typeform, joins Rina Alexin to reveal how she’s leading an AI transformation that’s as human as it is technical. From breaking down walls between product and engineering to turning procurement into a partner in innovation, Aleks shares how clarity, trust, and experimentation turned Typeform into a 100× organization. 

Key Topics Discussed in This Episode 

Culture Before Code 

Why trust, context, and collaboration between product, design, and engineering matter more than any tech stack when building AI-ready teams. 

Procurement Is the New Power Move 

How Aleks turned procurement into an innovation engine — re-designing processes to safely pilot 10 AI tools at once without derailing the organization. 

Metrics That Matter 

From 200 percent more PRs to shipping integrations in hours (instead of quarters) — what AI adoption looks like when you measure clarity and observability, not just hype. 

Why Listen to This Episode? 

In this episode, you’ll learn how to: 

• Define what “AI-first” actually means for your organization. 

• Lead cross-functional teams through change without burnout or chaos. 

• Turn procurement and legal from roadblocks into allies. 

• Measure AI success through clarity and observability (not vanity metrics). 

It’s a masterclass in leading AI transformation without losing your team’s trust (or your sanity). 

Related Resources 

Check out these additional tools and resources to add to your PM belt: 

• Productside Resource Library 

• More Productside Stories Podcast Episodes 

• Explore Productside Courses 

The Future of AI Product Management with Digvijay Singh (YouTube Ads) 

AI has been around for a while now but the PM role within it is evolving faster than ever. In this episode, Digvijay Singh, Senior Product Manager at YouTube Ads, joins Rina Alexin to unpack the three layers of AI Product Management: infrastructure, models, and applications. From writing evals to training “intern” models, Digvijay reveals how PMs can stay relevant, build better AI intuition, and turn machine learning into meaningful product outcomes.

Key Topics Discussed in This Episode 

The Three Layers of AI PM 

How product management splits across infrastructure, model, and application layers—and what each one demands from PMs today. 

The Power of Evals 

Why writing evals is the new success metric for AI PMs—and how it helps teams reduce hallucinations and clarify goals. 

Product Intuition in the AI Era 

How “playing” with AI tools builds better intuition, sharper judgment, and stronger PM instincts in a rapidly changing space. 

Why Listen to This Episode? 

In this episode, you’ll get: 

• A clear framework for navigating the three tiers of AI Product Management. 

• Practical advice for PMs transitioning into AI-focused roles. 

• Real-world examples from Digvijay’s work at YouTube Ads and Google. 

• Tips on developing product intuition by experimenting with AI tools. 

  
  

Whether you’re building LLM-powered apps or just learning to manage your “AI intern,” this episode will help you stay one step ahead. 

Related Resources 

Check out these additional tools and resources to add to your PM belt: 

• Productside Resource Library 

• More Productside Stories Podcast Episodes 

• Explore Productside Courses 

Trailblazing Women in Product Management with Pinky Panjwani

In this episode, Nicole Tieche sits down with Pinky Panjwani, Director of Product Management for Striven at Miles Technologies, to talk about what it means to lead through learning. From crossing the chasm to building a team culture rooted in growth and simplicity, Pinky shares how persistence, patience, and a sharp sense for clarity have shaped her 22-year career. Ever wondered how to keep your team inspired while still chasing business outcomes? This one’s for you. 

Key Topics Discussed in This Episode

Why Listen to This Episode?

This energizing convo gives you:

• A fresh take on product-led growth — and how to make your product sell itself. 

• Simple frameworks for fostering trust and learning across distributed teams. 

• Real-world tips for communicating across stakeholders without losing clarity. 

• A mindset shift on persistence over instant gratification in product work. 

  
  

Proof that great PMs don’t just build products. They build patience, persistence, and people. 

Related Resources 

Check out these additional tools and resources to add to your PM belt: 

• Productside Resource Library 

• More Productside Stories Podcast Episodes 

• Explore Productside Courses 

Building Platform Products That Scale — Without Drowning in Stakeholders 

Platform products are some of the most complex beasts in product management. They have to serve multiple teams, stay flexible, and scale across the org—all while keeping technical and business needs in sync. In this episode, Rina Alexin chats with Aindra Misra, Director of Product Management for AI, Data, and Developer Experience at BILL (and former Twitter PM), about how to bring structure to platform chaos, build for scale, and win over even the loudest stakeholders.

Key Topics Discussed in This Episode

What Makes a Great Platform PM

Why platform product management is the sweet spot for technically curious PMs—and how mindset matters more than your coding background. 

The Art (and Science) of Prioritization

Aindra’s framework for balancing competing use cases, weighing business impact, and keeping the long-term platform vision intact. 

Stakeholder Alignment Without the Drama

How to turn “fight for priority” meetings into data-driven discussions that build stronger teams and better platforms. 

Why Listen to This Episode?

What will you get out of this discussion? 

• In this thought-provoking conversation, you’ll gain: 

• A framework for prioritizing platform features by impact, effort, and strategic value 

• Real talk on managing competing stakeholders (and surviving to tell the tale) 

• Insight into “horizontal thinking” and why it’s key to scalable platforms 

• Lessons from Twitter and BILL on how to balance speed, flexibility, and tech debt 

If you’ve ever tried to scale a platform product (or want to move into this space) this is your playbook. 

Related Resources

Check out these additional tools and resources to add to your PM belt:

• Productside Resource Library 

• More Productside Stories Podcast Episodes 

• Explore Productside Courses 

Jose Quesada on Discovery, Strategy, and the Value of Product Management 

Jose Quesada, VP of Product Management at American Express, joins Rina Alexin to unpack how Amex built a globally recognized mobile app by running discovery and delivery in parallel. From killing bad ideas quickly to making strategy concrete, Jose shows how product leaders can balance long-term vision with day-to-day execution... all while keeping skeptical stakeholders on board. 

Key Topics Discussed in This Episode 

Discovery ≠ delivery 

Why Amex runs two tracks in parallel and why “killing hypotheses” is as valuable as proving them. 

Stakeholder judo 

How to align skeptics, win champions, and use communication, relationships, and data to build trust. 

Strategy that sticks 

Building blocks of a good strategy, why context is everything, and how to link product bets to company goals.

Why Listen to This Episode? 

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

• A practical model for running discovery and delivery in parallel 

• Tactics for disproving bad ideas fast (and celebrating the red) 

• Stakeholder management techniques that actually lower friction 

• A blueprint for building strategies that align with business context 

If you’re tired of being told “be more strategic” without any how-to, this conversation will give you concrete tools and mindset shifts you can use tomorrow. 

Related Resources 

Check out these additional tools and resources to add to your PM belt: 

• Productside Resource Library 

• More Productside Stories Podcast Episodes 

• Explore Productside Courses