Productside Stories

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 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 

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 CraigWhen 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 Episode1. 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 ResourcesCheck out these additional tools and resources to add to your PM belt:Productside Resource LibraryMore Productside Stories Podcast EpisodesExplore Productside Courses