1442980948
The Way of Product with Caden Damiano

Advertise on podcast: The Way of Product with Caden Damiano

Rating
★★★★☆
3.8
from
6 reviews
This podcast has
173 episodes
Language
English
Publisher
Caden Damiano
Explicit
No
Date created
2018/11/16
Latest episode
2026/01/21
Average duration
45 min.
Release period
14 days

Description

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

Unlock The Way of Product with Caden Damiano podcast Email contact info,
Listeners & Audience details

Email contact information

Direct podcast contact details

Listeners

Audience numbers & engagement insights

Audience details

Podcast Insights

Podcast episodes

Check latest episodes from The Way of Product with Caden Damiano podcast


#156 How to Inspire, Align, and Amplify Innovative Teams w/ Keith Lucas, former CPO/CTO at Roblox
2026/01/21
Keith Lucas is a startup advisor specializing in product, growth, people, and culture who previously served as Chief Product Officer and Chief Technology Officer at Roblox, where he helped transform the platform into a global ecosystem for tens of millions of creators and players. Rising to prominence in the 2010s, he became known for building engines of innovation inside entrepreneurial teams, uniting long-term mission, values, and execution into a single operating system for high-output organizations. He is the author of Impact: How to Inspire, Align, and Amplify Innovative Teams, a 202-page playbook published in 2025 that codifies these practices for leaders across high-growth technology, gaming, and AI-driven companies. Previously, as Chief Product Officer and later Chief Technology Officer at Roblox, Lucas led the product and engineering organizations through one of the strongest multi-year growth runs in the company’s history, helping drive player and revenue expansion of roughly 300–400% year over year heading into 2016. He scaled the product organization from a single product manager and a small design and analytics group to a 30-person, data-driven team, while guiding engineering from bi-weekly releases to daily and weekly cadences across web and core client surfaces. During this period, he helped architect the platform’s shift to mobile-first growth, global game server distribution, and a more systematic approach to discovery and developer incentives, contributing to annual revenue that would later be reported in the billions of dollars as the company matured. His career highlights include serving as Chief Operating Officer at Instrumental, an AI-powered manufacturing intelligence company where he helped the business grow its customer base across consumer electronics, automotive, and medical devices as revenue expanded by an order of magnitude in the wake of its Intercept product launch. Over two decades in technology, he has held senior roles across engineering, operations, and business, from early-stage leadership at Roblox to advisory work with startups in AI, gaming, entertainment, and enterprise software, bringing a portfolio of experience that spans platform infrastructure, creator ecosystems, and go-to-market strategy. Lucas holds a Ph.D. in Aeronautics and Astronautics from Stanford University and a Master of Public Policy from the University of California, Berkeley, a combination that underpins his analytical approach to building enduring, institution-scale teams. As author of Impact: How to Inspire, Align, and Amplify Innovative Teams, he codifies a two-tier framework that helps leaders avoid stalled scaling, culture dilution, and loss of focus by treating culture as a system and leadership as a discipline. He now works directly with founders, CEOs, and executive teams as a trusted advisor, helping them design what he calls “engines of innovation” that can sustain compounding impact over decades rather than single funding cycles. Listen on Spotify Listen on Apple Podcasts Innovative teams do not stumble into great products They intentionally build engines of innovation in how they hire, promote, and operate day to day. Keith Lucas has seen both well run and badly run startups, and the pattern he cares about is deceptively simple: Purpose-driven companies that adopt a long-term, institution-building mindset have a structural edge over those optimized for short-term financial wins.​ When Keith thinks about building entrepreneurial teams, he looks for five “non-negotiables”: * Can this person elevate the team’s ability to create, innovate, or solve problems? * Do they align with the values? Do they want the same long term outcomes? * Do they believe in the mission? * Can they live with the team’s non-negotiable principles? * Do they meet the minimum standards of mastery and autonomy? Teams that take those standards seriously quickly surface who needs too much handholding or who does not care enough about quality, because the realized culture will not support them.​ Here’s a practical nugget you can take from this episode today (though I recommend you listen to the whole thing, it’s one of the best episodes on leadership) His favorite hiring and team staffing question for sussing out these non-negotiables is something I am going to steal: When you have a free moment at work, where does your mind go? The answer exposes intrinsic motivation, and great leaders use that signal to dial in roles so that enthusiasm, skill, and impact line up instead of grinding against each other.​ Underneath all of this is a simple thesis: if you want an engine of innovation, you need people who behave like mission athletes—mission driven, performance oriented, continuously growing, and elevating their peers—and you need to give them aligned autonomy instead of micromanaged checklists. This episode is for builders who care about creating something enduring rather than chasing short-term wins, and who are willing to design their hiring, culture, and leadership practices to match that ambition.​ Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#155 Building Traction in the Age of AI + How New Design Tools are Revolutionizing Hardware Development w/ Matthias Wagner Founder/CEO of Flux.ai
2026/01/19
Matthias Wagner is the Founder and CEO at Flux, the AI-native hardware design platform streamlining how teams build printed circuit boards and electronics at scale. Rising to prominence in the late 2010s, he became known for transforming manual, spreadsheet-driven supply chain and PCB workflows into cloud-first, collaborative systems used by distributed engineering teams worldwide. Previously, as Product Manager at Facebook (now Meta), he led the Moments App, AR ads, and Oculus VR initiatives, working on products that collectively reached hundreds of millions of users globally. During his nearly three-year tenure, he operated at the intersection of machine learning, consumer-scale experimentation, and hardware-enabled experiences, which directly informed Flux’s AI-first approach to electronics design. His career highlights include co-founding 42media group in 2004 and bootstrapping it into a multi-million-euro digital signage and media business serving enterprise clients such as IBM, McDonald’s, DHL, Volkswagen, and major German financial institutions. He also co-founded Hochzeit.de, a wedding marketplace with planning and budgeting tools that grew into a leading German platform connecting thousands of couples with venues and vendors, and he has mentored multiple startup cohorts, helping dozens of founders move from idea to growth-stage businesses. Listen on Spotify Listen on Apple Podcasts Ship platforms that make hardware iteration feel like modern dev tooling. Matthias Wagner asked an Apple engineer about managing the iPhone supply chain. “What software do you use?” “What software? Cubicles full of people. Each one has a phone and a list of numbers. They call suppliers all day, updating a shared spreadsheet. One person can edit at a time.” That’s the terrain. Not what the frameworks say. Not what the business models teach. The actual terrain. Summer 2019, Matthias left Facebook to build electronics in his Oakland workshop. Got frustrated immediately. The tools hadn’t evolved since the mid-nineties. No version control, no collaboration, no automation. Just paper processes ported to Windows. The map said hardware was hard because manufacturing was expensive and inaccessible. He tested it. Ordered any semiconductor in the world to his backyard. Unit quantity: one. Seven-day turnaround from China. A few hundred dollars. The supply chain had democratized completely. The design tools hadn’t budged. At Facebook, machine learning had transformed everything. Why not here? A friend told him, “Matthias, you’ve been complaining about this all summer. Do something about it.” That’s Flux.ai. Making hardware design as accessible as software development. But here’s the pattern: most builders read the map and execute. Matthias walks the terrain and observes. The anecdotes don’t match the data. The frameworks don’t capture the friction. The best practices miss the opportunities. He doesn’t trust what frameworks say should be true. He tests what is actually true. Sources information directly. Builds messy models. Notices the friction everyone accepts as baseline. The map said hardware required massive capital and factory connections. The terrain showed the real constraint was tools nobody had fixed in thirty years. That gap between map and terrain? That’s where opportunities hide. Most product strategy happens in conference rooms. You fill out canvases and positioning statements. Run the plays from the playbook. But you’re optimizing against a map, not reality. The reality is cubicles and phone calls managing materials for the iPhone. The reality is CAD software that looks identical to 1995. The reality is sourcing spreadsheets with single-user edit locks in 2025. These aren’t exceptions. This is how things actually work. You can’t spot that from the map. You have to walk the terrain. Get your hands dirty. Build something yourself. Ask the engineer doing the work how they actually do it. Test your assumptions with first-hand experience. That’s how you develop real product sense. That’s how you see opportunities others miss by trusting frameworks that describe a world that doesn’t exist. The map is where you start. The terrain is where you build. Listen on Apple Podcasts ↗ or Spotify ↗ Guest: Matthias Wagner * LinkedIn: Matthias Wagner ↗ * Company: Flux.ai ↗ Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#154 Tactics for Product Launch Success & The Hidden Secrets of Making Products that "Just Work" w/ Dan De Mars, Head of Product at Current Backyard
2026/01/12
Most teams aren’t doing the work to make a product launch successful. They’re pontificating in conference rooms. Debating specs. Trying to intellectually arrive at the right answer. The work looks different. The work looks different. Like Steve Jobs said, “There’s just a tremendous amount of craftsmanship in between a great idea and a great product… Designing a product is keeping 5,000 things in your brain and fitting them all together in new and different ways… And it’s that process that is the magic.” It looks like Dan De Mars and his team at Current Backyard are cooking 500 pizzas in two weeks. Prototyping. Testing with real data. Seeing if they can actually deliver before promising anything to the public. Crust thickness. Topping load. Heat curves. App guidance. Mouthfeel. Every variable they could isolate became another run, another data point, another step toward something that felt right—not just something that looked good in a deck. This is what intentional design actually looks like. Dan, head of product at Current Backyard ↗, doesn’t believe in perfection out of the gate. He believes in creating the conditions where a team can learn fast, fail often, and use their collective taste to sort signal from noise. The result? An electric pizza oven that lets a first-timer cook restaurant-quality pizza without the friction, the learning curve, or the open flame. But the insight goes beyond pizza ovens. Great products feel inevitable from the outside because teams did unreasonable amounts of work on the inside. They ran tight feedback loops. They invited more eyes. They treated taste as a filter over hundreds of experiments, not a single flash of genius. Dan also talks about designing for “limited grillers”—urban dwellers constrained by space, fire restrictions, or time—who still want great food without the heroics. It’s a masterclass in finding underserved segments and building for real constraints. If you’ve ever wondered how “it just works” products come together, this conversation is the blueprint. Listen on Apple Podcasts ↗ or Spotify ↗ Links Dan De Mars on Linkedin ↗ Current Backyard ↗ 00:00 The Essence of Design 01:17 The Journey of a Designer 02:17 Philosophy of Design 03:25 Unlearning and Relearning 09:44 Innovating Outdoor Cooking 18:41 Targeting the Modern Cook 25:56 Innovative Launches and Product Expansion 26:52 Competing with Convenience: The Pizza Oven 28:26 Designing for User Experience 31:05 Prototyping and Iteration Process 34:31 Balancing Functionality and Aesthetics 44:29 Final Thoughts and Future Directions Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#153 Exec's Guide to Streamlining AI Integration: Unlocking Speed and Innovation in Business w/ David Trier, VP of Product at ModelOp
2026/01/05
Enterprises do not have an AI problem; they have an AI governance problem. In my recent conversation with David Trier, VP of product at ModelOp, he described the current state inside large organizations as “the Wild West of AI”—dozens of teams, hundreds of tools, and no shared way to get models safely into production. The reality is that many enterprises are staring at portfolios of 50 to 100 generative AI use cases, but only a handful ever make it into production, often taking six to 18 months to ship. What clicked for me in this episode was David’s analogy: ModelOp is essentially ServiceNow for AI. ServiceNow gave IT leaders a consistent, auditable way to turn messy tickets into reliable service management. ModelOp does the same for AI initiatives: it sits at the enterprise layer, orchestrating 10 to 12 teams and systems—data, security, legal, risk, compliance, infrastructure—so AI projects move through a repeatable playbook instead of one-off review cycles. David walked through a financial-services case where this approach cut time-to-production in half, turning 18‑month science projects into AI services that ship in weeks and generate business value before models degrade. For product leaders and CTOs, the takeaway is simple: if AI is a C‑suite–sized investment, it needs C‑suite–grade governance, not grassroots experimentation scattered across the org. If you are thinking about how to move from proof‑of‑concept chaos to an enterprise AI operating model, this episode is worth your time. Listen on Apple Podcasts ↗ or Spotify ↗ Mentions * ModelOp ↗ * David Trier ↗ Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#152 How AI has redefined Intercom's product strategy, team dynamics & pricing w/ Brian Donohue, VP of Product at Intercom
2025/12/01
Show Notes: 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. 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. 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. Connect with Brian on LinkedIn Listen to The Way of Product: Apple Podcasts or Spotify Actionable Takeaways✅ Embrace the uncertainty and potential of AI-driven product innovation. ✅ Aligning incentives through outcome-based pricing instead of traditional SaaS models. ✅ Balancing traditional product management structures with innovative AI development approaches. Time Stamps 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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#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
2025/11/17
In this episode, Vishal Khanna, Head of Product and Technical Go-To-Market at Exa.ai, 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.Connect with Vishal 01:14 Choosing to Work at Exa 01:24 The AI Revolution and Its Impact 02:25 Challenges and Opportunities in AI 04:30 Managing Expectations with AI 05:28 The Role of Product Managers in the AI Era 11:23 The Importance of Technical Literacy 22:25 Lessons from McKinsey 25:52 Adapting to AI in Product Management 33:04 The Concept of Agency 39:31 Conclusion and Final Thoughts Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#150 Thriving with ADHD: Entrepreneurship for Neurodivergent Minds w/ Jaime Toyne, ADHD Coach @ Flowjo
2025/11/10
This one myth, in my opinion, is the leading cause of burnout: Unless you aim for the highest role at a company, you’ve somehow failed. My next guest on The Way of Product Podcast, Jamie Toyne, challenges that idea. 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. 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. 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. 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. 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. 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. -CadenListen to The Way of Product: Apple Podcasts or Spotify 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. 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. LinkedIn: https://au.linkedin.com/in/jamietoyne1 Free 1:1 ADHD Coaching Session: www.jamietoyne.com 00:30 Journey to San Francisco—and burnout 02:15 Life as a Digital Nomad 03:48 ADHD Diagnosis and Early Life 05:07 Tennis Career and Education 08:44 Entrepreneurial Challenges and Burnout 13:48 Balancing Ambition and Lifestyle 18:46 Reflecting on Business Structure and Superpowers 19:11 Dealing with Imposter Syndrome and Financial Decisions 20:35 Team Dynamics and Company Culture 22:50 Passion for Coaching and Exit Planning 26:50 ADHD and Leadership Challenges 33:14 Finding Flow and Realigning with Passion Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#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
2025/11/03
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.” Key Topics Discussed: * The Mural integration trap: How responding to customer feature requests can lead to becoming an integration factory * Output vs. outcome-driven roadmaps: Why shipping features fast matters less than scaling the right thing * The validation framework: Moving from idea to experiment to validated roadmap before building * Qualitative vs. quantitative data: When to trust customer anecdotes over usage metrics * Zero-to-one product development: Building without data in early-stage companies * Meeting equity and hybrid work: How Neat approaches designing for distributed teams * Simplicity in hardware: The phone camera principle and why accessibility beats perfection Key Quotes: “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?” “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.” “The hardest word in product isn’t ‘no’—it’s ‘wait.’” “Often moving slow is a problem...but I think a bigger problem is not scaling the right thing.” Featured Story: 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. Resources Mentioned: * Book: Escaping the Build Trap by Melissa Perri * Neat’s App Hub marketplace * Product Kata framework About the Guest: 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. Connect with Kritarth: https://www.linkedin.com/in/kritarthsaurabh/ About NeatNeat manufactures video conferencing devices designed to keep meetings simple and equitable, whether participants are in-office, remote, or hybrid. Their products include the Neat Board Pro, an all-in-one 65-inch integrated screen with camera and speaker capabilities. Subscribe: www.wayofproduct.com Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#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
2025/10/06
I used to say, “Don’t let AI do your research.” I’ve changed my mind. 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. 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. If OpenAI sees enough value to combine forces, the way Margaret and her team work is worth studying. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. Here’s where I’ve landed: * 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.” * I’m biasing toward live learning and away from document theater: fewer perfect specs, more real outcomes. * 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). 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. 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. Listen to The Way of Product: Apple Podcasts or Spotify 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. Listen to The Way of Product: Apple Podcasts or Spotify 00:00 Introduction to AI and Human Judgment 00:33 Meet Margaret Ann from Statsig 01:16 Debating the Future of Jobs in Tech 02:45 The Importance of Taste in Product Management 06:34 Soft Skills and Human Empathy in Tech 12:33 The Role of Engineering Background in Product Leadership 15:46 AI's Impact on Research and Data Gathering 20:23 Embracing Technological Progress 20:42 The Joy of Creating with AI 22:18 AI in Product Management 24:32 The Future of Work with AI 25:45 Exploring AI Tools and Their Impact 31:23 The Role of AI in Knowledge Management 34:21 Optimism for the Future 35:25 Closing Thoughts and Encouragement Thank you for reading this week's episode of The Way Product. This publication is intended to be free indefinitely. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#147 How AI can "unlock" SaaS instead of killing it and when declining monthly usage can be a good thing in the world of AI agents w/ Andrew Saxe, VP of Product at Smartling
2025/09/08
Declining MAU can be a product win, depending on your product strategy... Andrew Saxe, VP of Product at Smartling, joined me to unpack why. When a system translates intent well and runs in the background, people don’t have to log in—and the work still gets done. We discussed designing for “manage by exception,” placing guardrails where failure would be costly, and allowing automation to carry the load. We looked at the feature request funnel too: why thousands of asks don’t equal thousands of tickets, and how building a few verbatim specs for large customers can still lead to unused features, tech debt, and wasted opportunities. Listen to The Way of Product: Apple Podcasts or Spotify Timestamps: 02:48 The niche translation industry and Smartling’s impact 11:28 The role of AI in translation 13:55 AI’s impact on Smartling’s product roadmap 16:38 Managing translations with AI and human oversight 22:00 Optimizing translation services for market expansion 22:47 Challenges and nuances of multilingual customer research 23:41 The art and science of requirements to spec translation 29:18 Feature requests and customer feedback 31:26 The importance of understanding user needs 34:27 The future of translation and AI 38:37 Concluding thoughts and contact information 24:56 AI and Translation: Balancing Automation and Human Touch 28:19 Feature Requests and Customer Feedback 30:27 The Importance of Understanding User Needs 35:42 Managing Translation Budgets and Quality 37:39 Conclusion and Final Thoughts Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#146 Mastering Proactive Product Messaging & FinTech Innovations with Michael Scully Head of Product at Summer
2025/08/25
Michael Scully reviewed all 1,000 applications personally when he posted a product manager role last August. Every. Single. One. That same obsessive attention to overlooked details drove him from coding in his dorm room to leading product at Summer, a public benefit corporation tackling America's $1.8 trillion student loan crisis. In our conversation, Michael discovered something shocking: The majority of people defaulting on student loans qualified for affordable payment plans—they just never knew these options existed. During the pandemic payment pause, borrowers' loans got sold, addresses changed, autopay broke. Prime credit scores tanked overnight through no fault of the borrower. "We're not dealing with edge cases," Michael explains. "These are normal people who did everything right, caught in a system that's surprisingly complex for what should be simple." We cover: → Diverse teams catch problems homogeneous ones miss (hire for "culture add" not "culture fit") → Where there's confusion, there's opportunity to help at scale, and how to spot opportunities. This episode covers student loan solutions. But it's really about building products that meet people where they struggle most—and the leadership philosophy that attracts top talent to mission-driven work. Timeline: 03:01 FinTech Trends and Student Loans 04:07 Challenges in Student Loan Management 05:58 Summer's Approach to Solving Student Loan Issues 10:48 Employer Benefits and Financial Wellness 14:45 Navigating Regulatory Changes 17:37 Product Management Insights 20:09 Proactive Messaging and Customer Experience 29:06 Hiring and Team Building Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
Ep145: How to Boost Your Creative Confidence, Taste & Close the Creativity Gap Using AI w/ Ben Rennie, Co-Founder of Reny
2025/08/18
Human-centered design, for all its merits, sometimes fails to consider what comes after the launch, after the product leaves our hands. We need a systemic approach: design that asks not only what people need now, but what the world will require in five, ten, or fifty years. It is a question of stewardship. As we rush to integrate AI and other technologies, are we thinking beyond the next quarter, the next release cycle? Are we willing to accept responsibility for the unintended consequences? AI, for its part, is neither savior nor villain. Ben Rennie sees it as an amplifier—a tool that accelerates the work but does not replace the worker. For example, he used AI to help finish his book, but the ideas and the voice are his own. The lesson is clear: technology can be a partner, but it cannot do the hard work of thinking, of feeling, of connecting the dots that only a person can see. When I write, using AI as an editorial partner, primarily for packaging ideas rather than generating them, has been a game-changer in helping me express myself. To the world better. So I'm happy to present Ben and his interview on the podcast, where we dive deep into where creative work is going in the age of generative AI. -Caden “80% of the world’s climate challenges today stem from the design phase of a product or service. We’re building things without recognizing the impact. Human-centered design means designing for people, but we often ignore the systems in which humans exist.”- Ben Rennie Listen now on Apple and Spotify. In this episode, I speak with Ben Rennie, co-founder of Reny®, about his career as a designer and entrepreneur spanning more than a decade. Ben shares how he started his consultancy in 2009, explains its evolution, and discusses challenges he has faced and lessons he has learned along the way. The conversation explores systemic design and why understanding the broader impacts of human-centered design matters. Rennie introduces his book, Lessons in Creativity, in which he examines the creativity gap and explains how fear can stifle creative confidence as people grow older. We also discuss the relationship between creativity and artificial intelligence, challenges in sustainable design systems, and stories from Rennie’s experience that highlight the importance of perseverance and bravery in creative work. The episode offers practical insights for anyone interested in creativity, technology, and human-centered design from a veteran in the creative industry. If you want to learn more about Ben Rennie, his work, or his thinking on creativity and design, check out the following: * Ben Rennie on LinkedIn — Connect with Ben and follow his latest updates. * Lessons in Creativity on Amazon — Explore Ben’s book for stories and strategies to cultivate your creative confidence. * Reny® (Ben’s agency) — Discover the consultancy Ben founded and see their latest projects. Timeline 00:12 Starting the Business Journey 00:28 Personal Reflections and Challenges 01:01 The Importance of Systems and Design 01:25 Balancing Personal Life and Work 02:45 Discussing the New Book 03:03 Exploring the Creativity Gap 07:07 Systemic Design and Environmental Impact 17:31 The Role of AI in Creativity and Work 27:04 Exploring Human-Centered Design 27:37 AI Tools for Enhanced Productivity 31:25 Transition Design and Future Innovations 34:33 Creative Confidence and Overcoming Fear 35:46 Personal Stories of Creativity and Bravery 46:07 The Importance of Meaningful Work Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
Ep144: Mastering Product Feedback Loops & Unlocking AI's Potential in B2B SaaS w/ Kareem Mayan
2025/08/11
“The data leads you. It does not tell you exactly where to go, but it offers suggestions about the direction to take your product. My business partner and I had a suspicion that we were prioritizing the wrong features. Instead of asking customers directly for feedback, we observed their behavior and used that data to inform our product decisions. Historically, product managers have wanted product feedback, but it is often difficult to collect and use. The rise of APIs has made gathering feedback much easier, yet many product managers remain stuck in older ways of working. It is tempting to say, “I want to build this,” and assign ten or twenty developers to work on pet features. We believe that model of product management is fading. You will increasingly rely on data—both customer and qualitative data—because if competitors do so, they will be closer to the customer, serve them better, and you risk falling behind. In a world where intelligence is widely accessible and anyone can build nearly any feature at minimal cost, what truly matters? I am not one to make predictions, but a few factors stand out as difficult to replicate:” -Kareem Mayan Listen now on Apple and Spotify. In this episode, we’re joined by Kareem Mayan, co-founder of Savio. Savio.io is a product management platform that centralizes and organizes customer feature requests and product feedback, enabling B2B SaaS teams to build evidence-based roadmaps and prioritize features that matter most. Kareem has more than two decades of experience in product management and entrepreneurship—including roles at ESPN and MySpace, and three successful startup exits. Here’s what we cover in the episode: * Transforming product management and SaaS operations with AI, machine learning, and automation * Building user-centric products through deep customer understanding and feedback * Centralizing and acting on customer feedback with integrated tools and platforms * Making data-informed decisions by blending analytics with qualitative insights * Preventing churn proactively using predictive analytics and early warning systems Listen now on Apple and Spotify. Where to find the topics: 00:53 Lessons from Mayan’s first startup experience02:39 Insights from subsequent ventures05:05 The importance of sales and marketing07:10 Product management and customer feedback08:01 AI and the future of product development13:34 Qualitative feedback in B2B SaaS17:01 Starting the current company18:49 Transition to a mid-market strategy19:05 Prioritizing customer feedback19:32 Savio’s approach to feedback management20:36 Founders’ journey and insights21:52 Challenges and solutions in product management22:13 Data-driven product development26:57 Balancing big wins and incremental improvements31:49 Steve Jobs myths around customer feedback Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#143 Innovate Like LEGO with Community-Driven Product Development
2025/07/21
Hey Listener! Communities are more than just support forums; If deployed correctly, they can be a fantastic channel for product teams to sift signal from the noise. In the latest episode of Way of Product, I had the pleasure of chatting with Jake McKee, a seasoned community expert with over 20 years of experience working with companies like Apple, Lego, and clients such as Southwest Airlines and H&R Block. In this interview, I chat with him about his journey in the customer engagement space, working with major brands like Apple Global Support, Lego Global Community, and more. His expertise in creating community-driven product development strategies and operationalizing community feedback in large organizations like Apple offers unique insights for anyone looking to enhance their customer engagement programs. Listen now on Apple and Spotify. And if you like what you're listening to in this episode, I highly recommend checking out his work at jakemckee.com Actionable Takeaways ✅ Bridging the Gap Between Customers and Companies ✅ Empowering Customers to Become Advocates ✅ The Power of Relational Customer Engagement Time Stamps 02:45 An Introduction to Jake and His Journey in Community Development 06:22 Bridging the Gap Between Customers and Companies 13:10 Apple Community Insights 18:08 Operationalizing Community Feedback 27:45 Community-Driven Product Development 37:00 Challenges and Strategies in Community Engagement 46:30 Understanding Developer Needs Beyond the SDK 57:50 The Importance of Honest Communication 1:06:20 Creating Shared Success in Communities 1:15:05 The Power of Relational Customer Engagement 1:25:15 Final Thoughts and How to Get Started Bridging the Gap Between Customers and Companies "My work has always had some connection to bridging the gap between customer and company." —Jake McKee Jake emphasizes the importance of community programs over mere platforms. He believes in building long-term programs that foster genuine relationships between companies and their customers. This approach leads to better customer satisfaction and product development. Takeaway: Focus on bridging customer-company gaps through meaningful community programs, leading to enriching customer relationships and better product insights. For me, meaningful customer engagement means meeting them where they're at - at industry events—creating a third place where people could hang out at those events, like a lounge or a podcast. Apple invested heavily in SEO for its support community. So that if you looked up anything Apple-related, there would be a support community link. Empowering Customers to Become Advocates "You don't create fans without a relationship." —Jake McKee Jake discusses the power of empowering customers as advocates through transparency and open communication. He highlights how involving community voices in product development processes can lead to better products and product launches. Takeaway: Empower your customers by involving them in your processes, building trust, and creating advocates who support and promote your brand. To do that, customers need to feel seen, heard, and understood. They need to think that you're building on their behalf, that you're making their work possible, and that they feel empowered to share how fantastic your product is. The Power of Relational Customer Engagement "Think about relational activity, not just data gathering." —Jake McKee Jake shares that successful customer engagement relies on building genuine relationships rather than focusing solely on data collection. This relational approach encourages consistent and meaningful interactions with your audience, leading to long-term connections. Takeaway: Build relational connections with customers, treating engagements as social conversations to foster trust and long-term loyalty. You create loyalty by giving and establishing a sense of reciprocity. Doing things that you don't have to do as a company are great ways to generate reciprocity. That's another episode. Listen to the whole thing to get all the extra context that wasn't included in this post. Again, thanks for opening and listening. Cheers, Caden Damiano Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe
#142 The Question Product Leaders Aren't Asking That Can Boost Retention; Film Industry Insights for Innovation; And Building a Top Productivity App w/ Steven Puri, Founder of "The Sukha Company"
2025/07/14
Hey Listener! Today's guest is Steven Puri, CEO of The Sukha Company, which develops one of the most popular productivity and focus apps, Sukha. Connect with Steven on Linkedin. Listen now on Apple and Spotify. Steven has a diverse background in both the film and tech industries. As a former senior executive at major motion picture studios and a tech entrepreneur who has raised venture capital for startups, Steven brings a unique perspective on creativity and leadership. Here’s his IMDB page; he’s worked on films like Independence Day, Godzilla, and Braveheart. He shares some pretty awesome behind-the-scenes stories with directors like Roland Emmerich. He's a fantastic storyteller. I was hooked every time he told a story, and they were hilarious and entertaining. During our conversation, we discussed: ✅ The parallels between launching films and tech products and the challenges of scaling creative projects. ✅ The application of remote and hybrid work models from film production to today's tech environments. ✅ The impact of flow states on personal efficiency and keeping your team productive. Important Time Stamps: - 03:15 - Steven’s transition from film to tech - 12:30 - Adapting film production strategies to tech - 25:45 - Cultivating flow states for better productivity with Sukha Actionable Takeaways Break Down Big Tasks: Flow Gets Unlocked by Tackling a Manageable Chunk of Work Steven emphasizes the power of tackling big tasks by breaking them down into smaller, manageable steps. This provides your brain with a way to begin forming connections to the broader picture. "And if you do put something crazy on there, like, I have to write this week's episode, it suggests like the estimate on that is probably 16 hours. You're probably not gonna do it before your brain blows up. What if, instead of writing the episode, you did an act one outline?" - Steven Puri Takeaway: My favorite thing to do before writing a PRD, or when I was designing, was to focus on creating a wireframe or writing an outline to get to a v0 of a work output deliverable. That v0 work informs the gaps in my thinking, which provides different paths forward to make progress. Steven's approach here is influenced by decades of experience in the film industry, where phases are broken up into different levels of fidelity: storyboard, script, and logistical documents. The whole concept of pre-production is to break up the work into manageable chunks so that, if followed, you don't have to have as much thrashing in the production phase of a movie or TV show. The film industry has been using remote and hybrid work for decades Steven highlights the effectiveness of hybrid work, blending remote and in-person collaboration, as a way to adapt to current work environments. We've long recognized the necessary balance of structured planning and creative freedom in filmmaking, from remote idea nurturing and production intensity to remote post-production work.Hollywood has been doing remote for a very long time. You're writing a script at your house. You're creating storyboards and logistical documents on your iPad in a café. Hybrid work is when you're in the studio pitching a script or in the writer's room, roughing out final details. And production is when you're in the office. You're showing up to work every day. Sometimes 12+ hours a day. The beautiful thing about Hollywood production is that it respects all the different work locations and styles, encouraging creative results. "Belonging to a community enhances performance and motivation… Balancing remote and in-office work helps unlock creativity." - Steven Puri Takeaway: A hybrid model can maximize both focused independent work and team efforts. I'm a big fan of working from home to complete my IC tasks and collaborating on Zoom or Google Meet. However, those work trips, where we travel to a co-working space or fly out to an office, have been crucial in my experience for making those big strategic decisions. Balance your work schedule to harness the strengths of both approaches. Leverage Downtime for Creativity Steven encourages using downtime or even multiple projects to access creative insights that might otherwise remain untapped. He calls it the "other thing", and when managing teams, he tries to give writers, engineers, or designers another thing to work on so that if they're blocked in one area, they could go work on something else. "The great ideas happen when you're thinking about something else." - Steven Puri Takeaway: Embrace moments of mental wandering during routine tasks. These breaks can lead to innovative solutions and fresh ideas. I hope these takeaways provide you with actionable insights to enhance your productivity and creativity. Listen to the full episode to hear behind-the-scenes stories of films like Independence Day, Godzilla (the one with Matthew Broderick), and much more in the whole episode. Listen now on Apple and Spotify. Cheers, Caden Damiano Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

Podcast reviews

Read The Way of Product with Caden Damiano podcast reviews


3.8 out of 5
6 reviews
★★★★★
StizzMizz 2022/08/16
Caden and Design!!
Love the flow, info, and conversation. Keep it up!
★★★★☆
LexASZ 2021/05/19
Sound Quality
The sound quality in both the first and second episodes are horrible. It’s almost too hard to listen to but the information being presented is great. ...
check all reviews on apple podcasts

Podcast sponsorship advertising

Start advertising on The Way of Product with Caden Damiano relevant audience podcasts


What do you want to promote?