Productside Stories

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 

How Scientists and PMs Really Build: Dr. Christina Agapakis with Rina Alexin

A synthetic biologist who became a creative and marketing leader? Yes, please. In this kickoff to Season 4, Dr. Christina Agapakis (Founder, Oscillator; former SVP Creative & Marketing at Ginkgo Bioworks) joins Productside CEO Rina Alexin to explore the messy, very human loop between research, product, and story. From lab benches to launch plans, we talk silos, funding models, and the art of “staying with the trouble” when the real world refuses your neat roadmap.

Key Topics Discussed in This Episode

The science ↔ product tangle (not a pipeline):

Christina explains why discovery isn’t a tidy flowchart—it’s a back-and-forth hairball of hypotheses, constraints, and collaboration that looks suspiciously like modern product discovery. 

Funding, impact, and translating research:

Who pays shapes what gets built. We dig into grants, incentives, and new models (e.g., focused research orgs) that bridge lab breakthroughs to useful products without pretending it’s frictionless.

Personas for molecules vs. people:

Scientists often model cells; PMs model users. Christina makes the case for bringing real human context into upstream work—and why clear stories beat sterile slides when stakes are high.

Why Listen to This Episode?

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

• A fresh mental model for discovery that treats research like product (small bets, fast feedback). 

• Tactics for working across silos without losing craft (or outcome). 

• Language to translate messy reality into narratives stakeholders actually act on. 

• A reminder to “stay with the trouble” when ambiguity spikes and why that’s where impact lives. 

If you build things for humans (or with humans), this conversation will sharpen your process and your story.

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 

Product and engineering love to blame each other—but the best teams skip the turf war and figure out how to move forward together. In this episode, Rina talks with Guy Gershoni, Head of Engineering at genesIT, about what makes that partnership work (and what breaks it). From lean experiments to shared metrics to real talk about trust, this one’s packed with hard-earned lessons from someone who’s seen both the chaos and the magic. 

Key Topics Discussed in This Episode 

Why engineers care more about impact than frameworks 

Turns out, engineers don’t want to ship shiny features. They want to ship useful ones. The key is making the impact visible. 

Experiments that don’t waste time (or careers) 

Guy shares a dead-simple way to test new ideas without overinvesting—or getting stuck in analysis paralysis. 

The MAC Model: A cheat code for fixing team dynamics 

Mindset, Articulation, Capability. If your team is off-track, this framework can tell you exactly where things are breaking down. 

Why Listen to This Episode? 

In this episode, you’ll get: 

• Real advice on how product and engineering can stop talking past each other 

• A new way to think about experimentation (it’s not about frameworks) 

• Tactics to make success metrics a shared responsibility 

• A refreshingly honest take on what actually builds team trust 

If you’re navigating cross-functional tension or just want to collaborate better, this one’s worth your time. 

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