The Way of Product with Caden Damiano
The Way of Product with Caden Damiano

The Way of Product with Caden Damiano

Caden Damiano

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The Way of Product is your graduate school focused on developing a taste for what “great products” look like. Conversations are two professionals talking shop about positioning, segmentation, excellent product design, and most importantly, taste. www.wayofproduct.com

Recent Episodes

#152 How AI has redefined Intercom's product strategy, team dynamics & pricing w/ Brian Donohue, VP of Product at Intercom
DEC 1, 2025
#152 How AI has redefined Intercom's product strategy, team dynamics & pricing w/ Brian Donohue, VP of Product at Intercom
<p><strong>Show Notes:</strong></p><p>In the latest episode of the Way of Product Podcast, I had the pleasure of chatting with Brian Donohue, Vice President of Product at Intercom. Brian has been a critical player at Intercom for over 11 years, where he has navigated the company’s growth and transformation, especially in the ever-evolving world of AI integration.</p><p>Brian shared his insights and experiences in transforming product development at Intercom, focusing on building a Fin AI agent that’s set to redefine customer support.</p><p>With over two years dedicated solely to AI, Brian discussed the company’s journey from its early machine learning beginnings to embracing large language models.</p><p><a target="_blank" href="https://www.linkedin.com/in/brian-d-2450192/">Connect with Brian on LinkedIn</a></p><p><strong>Listen to The Way of Product:</strong> <a target="_blank" href="https://podcasts.apple.com/us/podcast/the-way-of-product-with-caden-damiano/id1442980948">Apple Podcasts</a> or <a target="_blank" href="https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV">Spotify</a></p><p><strong>Actionable Takeaways</strong>✅ Embrace the uncertainty and potential of AI-driven product innovation.</p><p>✅ Aligning incentives through outcome-based pricing instead of traditional SaaS models.</p><p>✅ Balancing traditional product management structures with innovative AI development approaches.</p><p><strong>Time Stamps</strong></p><p>04:15 AI Integration in Product Development07:40 Architectural and Product Thinking in AI11:05 Challenges and Innovations in AI Implementation18:00 Continuous Improvement and Reassessment24:50 Inherited Product Design Flaws31:35 Technical Rigor and Product Validation37:10 Evolving Product Management Practices42:15 The Role of AI in Modern Product Development49:20 Outcome-Based Pricing Explained55:00 AI Transformation and R&D Services59:30 Adapting Product Development to Customer Needs66:45 Final Thoughts and Future Outlook70:20 Connecting with Brian Donahue</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.wayofproduct.com?utm_medium=podcast&#38;utm_campaign=CTA_1">www.wayofproduct.com</a>
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48 MIN
#151 The Hidden Trait that Separates High-Agency PMs from the Rest, The Skill AI Can't Replace, w/ Vishal Khanna Head of Product @ Exa.Ai
NOV 17, 2025
#151 The Hidden Trait that Separates High-Agency PMs from the Rest, The Skill AI Can't Replace, w/ Vishal Khanna Head of Product @ Exa.Ai
<p>In this episode, <a target="_blank" href="https://www.linkedin.com/in/vishalkhanna7/"><strong><em>Vishal Khanna</em></strong></a>, Head of Product and Technical Go-To-Market at <a target="_blank" href="https://exa.ai/">Exa.ai</a>, shares insights on the ambitious mission to reinvent search in the AI-driven world. We talk about the challenges and opportunities in taking on industry giants, the importance of thoughtful application of AI tools, and the value of fundamental problem-solving skills. Vishal also discusses his transition from management consulting to product management, the necessity of technical literacy, and fostering high agency in teams. This conversation explores how integrating AI with sound decision-making can drive impactful innovation in the tech industry.<a target="_blank" href="https://www.linkedin.com/in/vishalkhanna7/">Connect with Vishal</a></p><p>01:14 Choosing to Work at Exa</p><p>01:24 The AI Revolution and Its Impact</p><p>02:25 Challenges and Opportunities in AI</p><p>04:30 Managing Expectations with AI</p><p>05:28 The Role of Product Managers in the AI Era</p><p>11:23 The Importance of Technical Literacy</p><p>22:25 Lessons from McKinsey</p><p>25:52 Adapting to AI in Product Management</p><p>33:04 The Concept of Agency</p><p>39:31 Conclusion and Final Thoughts</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.wayofproduct.com?utm_medium=podcast&#38;utm_campaign=CTA_1">www.wayofproduct.com</a>
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42 MIN
#150 Thriving with ADHD: Entrepreneurship for Neurodivergent Minds w/ Jaime Toyne, ADHD Coach @ Flowjo
NOV 10, 2025
#150 Thriving with ADHD: Entrepreneurship for Neurodivergent Minds w/ Jaime Toyne, ADHD Coach @ Flowjo
<p><em>This one myth, in my opinion, is the leading cause of burnout: </em></p><p><em>Unless you aim for the highest role at a company, you’ve somehow failed. </em></p><p><em>My next guest on The Way of Product Podcast, Jamie Toyne, challenges that idea. </em></p><p><em>Jamie’s been there and done that. he’s been the CEO, sold the company, and travelled the world. The right fit might be coaching, consulting, or serving as the creative force behind someone else’s vision—like Jony Ive was to Steve Jobs. </em></p><p><em>Following formulas that ignore your true nature leads to burnout and misalignment—success is not measured by title, but by how invigorating the work feels. </em></p><p><em>Enzo Ferrari, James Dyson, Dietrich Mateschitz (Redbull), Jony Ive, didn’t optimize for careers that make a bunch of money, they did work they unlocked their talents, gave them energy to be creative during the hard times, and the structure their creative expression. </em></p><p><em>If you are doing great work that aligns with your unique talents and values, the market will reward you, companies will fight to retain you, and people will want to invest or purchase what you build because you are involved.</em></p><p><em>Turns out, great work is hard to come by, and putting someone who’s energy isn’t aligned with the work doesn’t lead to great work. </em></p><p><em>This episode is for anyone who doesn’t feel like they are doing work that aligns with their wiring. I certainly benefited from the conversation. </em></p><p><em>-Caden</em><strong>Listen to The Way of Product:</strong> <a target="_blank" href="https://podcasts.apple.com/us/podcast/the-way-of-product-with-caden-damiano/id1442980948">Apple Podcasts</a> or <a target="_blank" href="https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV">Spotify</a></p><p>In this episode, Jamie Toyne recounts his personal and professional journey with ADHD—from growing up in Australia, building a successful mergers and acquisitions firm in San Francisco, to starting an ADHD coaching career. Jamie experienced significant burnout, moved to Mexico, and later sold his business.</p><p>He discusses the challenges and benefits of living with ADHD as a business leader, the importance of doing work that aligns with personal values, and how his coaching program helps people with ADHD perform better and prevent burnout. Jamie explores recent changes in how society understands ADHD, and what these shifts mean for modern workplaces.</p><p>LinkedIn: <a target="_blank" href="https://au.linkedin.com/in/jamietoyne1"><strong>https://au.linkedin.com/in/jamietoyne1</strong></a></p><p>Free 1:1 ADHD Coaching Session: <a target="_blank" href="https://calendly.com/jamietoyne/flowjo-free-coaching-call?month=2025-11">www.jamietoyne.com</a></p><p>00:30 Journey to San Francisco—and burnout</p><p>02:15 Life as a Digital Nomad</p><p>03:48 ADHD Diagnosis and Early Life</p><p>05:07 Tennis Career and Education</p><p>08:44 Entrepreneurial Challenges and Burnout</p><p>13:48 Balancing Ambition and Lifestyle</p><p>18:46 Reflecting on Business Structure and Superpowers</p><p>19:11 Dealing with Imposter Syndrome and Financial Decisions</p><p>20:35 Team Dynamics and Company Culture</p><p>22:50 Passion for Coaching and Exit Planning</p><p>26:50 ADHD and Leadership Challenges</p><p>33:14 Finding Flow and Realigning with Passion</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.wayofproduct.com?utm_medium=podcast&#38;utm_campaign=CTA_1">www.wayofproduct.com</a>
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40 MIN
#149 How to Spot When the Data is Lying & The Most Effective Framework for Hypothesis-Driven Development w/ Kritarth Saurabh, VP of Product at Neat
NOV 3, 2025
#149 How to Spot When the Data is Lying & The Most Effective Framework for Hypothesis-Driven Development w/ Kritarth Saurabh, VP of Product at Neat
<p>What happens when your biggest customer asks for a feature that seems perfectly rational—backed by data, supported by sales, and tied to six-figure deals? Kritarth Saurabh shares how Neat avoided the build trap by pausing to validate what customers actually needed versus what they requested. This conversation explores the difference between output-driven and outcome-driven roadmaps, and why the hardest word in product management isn’t “no”—it’s “wait.”</p><p><strong>Key Topics Discussed:</strong></p><p>* The Mural integration trap: How responding to customer feature requests can lead to becoming an integration factory</p><p>* Output vs. outcome-driven roadmaps: Why shipping features fast matters less than scaling the right thing</p><p>* The validation framework: Moving from idea to experiment to validated roadmap before building</p><p>* Qualitative vs. quantitative data: When to trust customer anecdotes over usage metrics</p><p>* Zero-to-one product development: Building without data in early-stage companies</p><p>* Meeting equity and hybrid work: How Neat approaches designing for distributed teams</p><p>* Simplicity in hardware: The phone camera principle and why accessibility beats perfection</p><p><strong>Key Quotes:</strong></p><p></p><p>“You gotta have the conviction to take a step back and say, look, what is the real outcome that I’m trying to drive here?”</p><p>“If I had just spent maybe the next quarter validating this as an experiment...what they would’ve told me is they want App X, they want Figma, they want Y...This is not about just making the dollar signs with the mural. This is about the wider customer problem.”</p><p>“The hardest word in product isn’t ‘no’—it’s ‘wait.’”</p><p>“Often moving slow is a problem...but I think a bigger problem is not scaling the right thing.”</p><p></p><p><strong>Featured Story:</strong></p><p>The Mural Integration Decision: Kritarth details how a seemingly rational request for a Mural integration—backed by top-three usage data and tied to major deals—would have led Neat down the path of building an integration team that services infinite requests. By spending a quarter validating the underlying customer need, they discovered enterprises wanted workflow integration across their entire app ecosystem. This insight led to building an App Hub marketplace instead, creating a platform that scales exponentially rather than linearly.</p><p><strong>Resources Mentioned:</strong></p><p>* Book: <em>Escaping the Build Trap</em> by Melissa Perri</p><p>* Neat’s App Hub marketplace</p><p>* Product Kata framework</p><p><strong>About the Guest:</strong></p><p>Kritarth Saurabh is VP of Product Management at Neat, a video conferencing hardware company focused on simplicity and meeting equity. Before Neat, he spent years in consulting at Boston Consulting Group, Accenture, and Deloitte, working with Fortune 500 companies and startups on product development. He started his career as a software engineer and has experienced the full product lifecycle from ideation to sunsetting.</p><p><strong>Connect with Kritarth:</strong> <a target="_blank" href="https://www.linkedin.com/in/kritarthsaurabh/">https://www.linkedin.com/in/kritarthsaurabh/</a></p><p><strong>About Neat</strong>Neat manufactures video conferencing devices designed to keep meetings simple and equitable, whether participants are in-office, remote, or hybrid. Their products include the <a target="_blank" href="https://us.neat.no/board-pro/?gad_campaignid=21546682704&#38;gbraid=0AAAAACnSryPG2ToxxOgefGsMpkPFERn9D#buy?utm_campaign=21546682704&#38;utm_adgroup=168233933999&#38;utm_source=google&#38;utm_medium=cpc&#38;utm_content=746747339981&#38;utm_term=neat%20board%20pro">Neat Board Pro</a>, an all-in-one 65-inch integrated screen with camera and speaker capabilities.</p><p><strong>Subscribe:</strong></p><p><a target="_blank" href="http://www.wayofproduct.com/"><strong>www.wayofproduct.com</strong></a></p><p></p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.wayofproduct.com?utm_medium=podcast&#38;utm_campaign=CTA_1">www.wayofproduct.com</a>
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43 MIN
#148 Why Soft Skills Are the New Hard Skills, Navigating the AI Revolution in Product Management & Design w/ Margaret-Ann Seger, Head of Product & Design at Statsig
OCT 6, 2025
#148 Why Soft Skills Are the New Hard Skills, Navigating the AI Revolution in Product Management & Design w/ Margaret-Ann Seger, Head of Product & Design at Statsig
<p><em>I used to say, “Don’t let AI do your research.” I’ve changed my mind.</em></p><p><em>That shift started before this interview—after I ran a complex API exploration through an AI research assistant and got back a thorough, sourced report with working links. </em></p><p><em>But my conversation with Margaret-Ann Seger (who leads product and design at Statsig, the intelligence infrastructure platform for feature flags, experimentation, and analytics) turned that insight into conviction. And the timing makes this even more interesting: Statsig recently announced it’s being aquired by OpenAI. </em></p><p><em>If OpenAI sees enough value to combine forces, the way Margaret and her team work is worth studying.</em></p><p><em>Here’s the core change I’m making in my own work: let AI collapse the paperwork so humans can concentrate on judgment. When I dump a messy outline into a model and it returns a clean structure in minutes, I don’t feel threatened; I feel focused. </em></p><p><em>Margaret described a world where PRDs update themselves from meeting inputs and auto-ticket the next steps. That’s not cutting corners. It’s cutting ceremony. The value we bring isn’t keystrokes—it’s synthesis.</em></p><p><em>Synthesis shows up in how we decide what to build when shipping gets cheap. AI lowers the barrier to creation, which raises the bar on taste. It’s not enough to ship more; you have to choose better—distill the real pain, reconcile what users say with what they actually do, and shape solutions that feel right in the hand. </em></p><p><em>Margaret triggered a new habit for me: I now write a one-paragraph “taste test” before we commit: Why this problem? Why now? Why this approach? If I can’t explain it plainly, we aren’t ready.</em></p><p><em>The conversation also reframed “soft skills” as the durable edge. You can’t paste three years of team history into a prompt. Reading the room, sensing when engineers don’t buy a solution, remembering why a past decision failed—these are still human advantages. Margaret called out the friction every PM knows: users tell you one thing in interviews and do the opposite in product. Someone has to hold both truths at once and decide. That someone is still us.</em></p><p><em>One practice of hers made that human edge tangible: make customer support everyone’s job. At Statsig, support isn’t a silo. They rotate it. Designers answer confused tickets and see where the UI collapses. Engineers feel the frustration firsthand and often fix root causes quickly. It’s tempting to route everything through a bot for speed, but there’s a hidden cost: you lose the raw empathy that powers taste. We’re piloting a similar rotation and tracking the fixes it sparks.</em></p><p><em>Another theme was moving learning into production. Prototypes were born when shipping was expensive. As that cost falls, high-fidelity demos give way to small, live experiments that gather real data. Margaret’s ideal cadence is to spend more time on problem analysis and then release multiple small bets behind flags. I’ve started doing the same for ambiguous flows: define two or three minimal viable variants, ship them to real segments, and time-box the learning window. Data beats debate.</em></p><p><em>On the tooling side, Margaret pushed me to point AI at sources of truth, not just the documentation. Docs always lag. Code doesn’t. Her team is exploring agents that answer questions grounded in the codebase and SDKs. I loved the example of customers repurposing Statsig’s experimentation tool to benchmark models and prompts offline—a reminder that good tools get bent into new jobs in the AI era. We’re trialing a code-aware path for technical support and an internal agent trained on our repos for integration questions.</em></p><p><em>Something else I’m now normalizing: don’t hide your AI usage. Margaret hired a PM who clearly used AI on the take-home. That wasn’t a disqualifier; the deciding factor was his judgment. The stigma needs to go. Show your work, raise the standard, and trade playbooks. We’re adding a simple line to retros: “How did AI help?” When the practice is visible, everyone gets better faster.</em></p><p><em>Two moments from the interview keep replaying for me. The first was our “soft skills” segment, because it names what PMs actually do when the tools get powerful: we arbitrate between truths, people, and paths. The second was personal and small—Margaret and her husband use AI to make songs for everyday moments and stories for their kid. It’s a reminder that this wave isn’t only about efficiency; it can unlock more human connection at scale.</em></p><p><em>Here’s where I’ve landed:</em></p><p>* <em>I no longer treat AI as a novelty or a threat. I treat it as an accelerant. It compresses the “what” so I can deepen the “why.”</em></p><p>* <em>I’m biasing toward live learning and away from document theater: fewer perfect specs, more real outcomes.</em></p><p>* <em>I’m putting empathy on the front line (support rotations), taste at the gate (the one-paragraph test), and code at the center of truth (repo-grounded agents).</em></p><p><em>If you’ve been skeptical like I was, start small: choose one active project, let AI handle the formatting and ticketing, and spend the saved hour with a customer or sharpening the problem statement. You may find your job doesn’t get smaller. It gets truer.</em></p><p><em>And in a world where a company like Statsig is merging with OpenAI, getting to that truer version of product work isn’t optional—it’s the edge.</em></p><p><strong>Listen to The Way of Product:</strong> <a target="_blank" href="https://podcasts.apple.com/us/podcast/the-way-of-product-with-caden-damiano/id1442980948">Apple Podcasts</a> or <a target="_blank" href="https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV">Spotify</a></p><p>Margaret-Ann Seger, leader of product and design teams at Statsig, and after the acquisition from OpenAI, part of their Product Staff, discusses the evolving role of AI in product management on the latest episode of The Way of Product. While AI can automate many tasks, human judgment remains crucial. She shares insights on how AI can supercharge productivity and reduce drudgery, allowing PMs to focus more on strategic thinking and deeper customer understanding. Margaret also explores the idea that future PM tasks will blend with design and engineering roles, facilitated by AI tools. She remains optimistic about AI's impact on creativity and productivity.</p><p><strong>Listen to The Way of Product:</strong> <a target="_blank" href="https://podcasts.apple.com/us/podcast/the-way-of-product-with-caden-damiano/id1442980948">Apple Podcasts</a> or <a target="_blank" href="https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV">Spotify</a></p><p>00:00 Introduction to AI and Human Judgment</p><p>00:33 Meet Margaret Ann from Statsig</p><p>01:16 Debating the Future of Jobs in Tech</p><p>02:45 The Importance of Taste in Product Management</p><p>06:34 Soft Skills and Human Empathy in Tech</p><p>12:33 The Role of Engineering Background in Product Leadership</p><p>15:46 AI's Impact on Research and Data Gathering</p><p>20:23 Embracing Technological Progress</p><p>20:42 The Joy of Creating with AI</p><p>22:18 AI in Product Management</p><p>24:32 The Future of Work with AI</p><p>25:45 Exploring AI Tools and Their Impact</p><p>31:23 The Role of AI in Knowledge Management</p><p>34:21 Optimism for the Future</p><p>35:25 Closing Thoughts and Encouragement</p><p><p>Thank you for reading this week's episode of The Way Product. This publication is intended to be free indefinitely. </p></p><p></p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.wayofproduct.com?utm_medium=podcast&#38;utm_campaign=CTA_1">www.wayofproduct.com</a>
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38 MIN