Productside Stories

Productside
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Welcome to Productside Stories, a product management podcast featuring honest conversations with experienced product leaders. We cover what it really takes to build successful, outcome-driven products: from strategy and discovery to delivery, leadership, and AI. Hosted by Productside, a product management training and consulting company, this podcast is designed for PMs and product leaders who want practical insight (not theory) for modern product work.

  1. AI, Agents, and Accountability

    12/02/2025

    AI, Agents, and Accountability

    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

    46 min
  2. Leading with Impact When the Stakes Are Water-Level High

    11/25/2025

    Leading with Impact When the Stakes Are Water-Level High

    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

    43 min
  3. Product-Market Fit, GTM, and Founder Myths with Shweta Agrawal

    11/17/2025

    Product-Market Fit, GTM, and Founder Myths with Shweta Agrawal

    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 Founders Keep Skipping Customer Discovery  Shweta explains why “I know the market because I am the market” is the fastest path to building something no one pays for — and how to break that pattern early. Product-Market Fit Signals That Actually Matter  Renewals, retention, usage depth, early-adopter behavior — and why the infamous “40% Would Be Very Disappointed” test still slaps in 2025. When (and Whether) You’re Ready for Go-to-Market  The building blocks founders overlook: ICP focus, positioning by region, partners who actually have reach, and the risks of going global before you even have 20 happy users.   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

    44 min
  4. From Retail Floors to Product Strategy: Building a Career Around Customers

    11/11/2025

    From Retail Floors to Product Strategy: Building a Career Around Customers

    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

    26 min
  5. From Layoff to Launch: Building an AI Business from the Ground Up

    11/04/2025

    From Layoff to Launch: Building an AI Business from the Ground Up

    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 LibraryMore Productside Stories Podcast EpisodesExplore Productside Courses

    34 min
  6. How Typeform Became AI-First (without Losing Its Human Touch)

    10/28/2025

    How Typeform Became AI-First (without Losing Its Human Touch)

    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

    55 min
  7. Inside AI Product Management: From Infrastructure to Innovation with Digvijay Singh of YouTube

    10/21/2025

    Inside AI Product Management: From Infrastructure to Innovation with Digvijay Singh of YouTube

    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

    37 min
  8. Sharpen the Saw: How Learning Fuels Product Leadership

    10/14/2025

    Sharpen the Saw: How Learning Fuels Product Leadership

    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 The accidental PM journey that turned into a 22-year product career. How Pinky went from software engineer to Director of Product Management — by “doing PM work before even knowing it was called PM.”  Turning learning into a leadership advantage. Why her team schedules “Sharpen the Saw” weeks to pause delivery and focus purely on growth.  Simplifying complexity. Why true product leadership isn’t about adding more. It’s about communicating less, better. 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

    21 min
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5
out of 5
3 Ratings

About

Welcome to Productside Stories, a product management podcast featuring honest conversations with experienced product leaders. We cover what it really takes to build successful, outcome-driven products: from strategy and discovery to delivery, leadership, and AI. Hosted by Productside, a product management training and consulting company, this podcast is designed for PMs and product leaders who want practical insight (not theory) for modern product work.

Information

  • Creator
    Productside
  • Years Active
    2024 - 2025
  • Episodes
    56
  • Rating
    Clean
  • Copyright
    © Productside
  • Show Website
    Productside Stories