The Way of Product with Caden Damiano

Brian Donohue, VP of Product at Intercom, shares his journey of integrating AI into product development, focusing on the creation of their AI agent, Finn. He discusses the evolution from early machine learning to leveraging large language models, reflecting on the significant challenges and innovations encountered. Brian emphasizes the importance of outcome-based pricing, aligning customer incentives with product success. He also explores the need for product teams to enhance their technical fluency to navigate AI complexities effectively.

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 Vishal01:14 Choosing to Work at Exa01:24 The AI Revolution and Its Impact02:25 Challenges and Opportunities in AI04:30 Managing Expectations with AI05:28 The Role of Product Managers in the AI Era11:23 The Importance of Technical Literacy22:25 Lessons from McKinsey25:52 Adapting to AI in Product Management33:04 The Concept of Agency39:31 Conclusion and Final Thoughts This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

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 SpotifyIn 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/jamietoyne1Free 1:1 ADHD Coaching Session: www.jamietoyne.com00:30 Journey to San Francisco—and burnout02:15 Life as a Digital Nomad03:48 ADHD Diagnosis and Early Life05:07 Tennis Career and Education08:44 Entrepreneurial Challenges and Burnout13:48 Balancing Ambition and Lifestyle18:46 Reflecting on Business Structure and Superpowers19:11 Dealing with Imposter Syndrome and Financial Decisions20:35 Team Dynamics and Company Culture22:50 Passion for Coaching and Exit Planning26:50 ADHD and Leadership Challenges33:14 Finding Flow and Realigning with Passion This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

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 perfectionKey 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 frameworkAbout 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

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 SpotifyMargaret-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 Spotify00:00 Introduction to AI and Human Judgment00:33 Meet Margaret Ann from Statsig01:16 Debating the Future of Jobs in Tech02:45 The Importance of Taste in Product Management06:34 Soft Skills and Human Empathy in Tech12:33 The Role of Engineering Background in Product Leadership15:46 AI's Impact on Research and Data Gathering20:23 Embracing Technological Progress20:42 The Joy of Creating with AI22:18 AI in Product Management24:32 The Future of Work with AI25:45 Exploring AI Tools and Their Impact31:23 The Role of AI in Knowledge Management34:21 Optimism for the Future35:25 Closing Thoughts and EncouragementThank you for reading this week's episode of The Way Product. This publication is intended to be free indefinitely. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

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 SpotifyTimestamps:02:48 The niche translation industry and Smartling’s impact11:28 The role of AI in translation13:55 AI’s impact on Smartling’s product roadmap16:38 Managing translations with AI and human oversight22:00 Optimizing translation services for market expansion22:47 Challenges and nuances of multilingual customer research23:41 The art and science of requirements to spec translation29:18 Feature requests and customer feedback31:26 The importance of understanding user needs34:27 The future of translation and AI38:37 Concluding thoughts and contact information24:56 AI and Translation: Balancing Automation and Human Touch28:19 Feature Requests and Customer Feedback30:27 The Importance of Understanding User Needs35:42 Managing Translation Budgets and Quality37:39 Conclusion and Final Thoughts This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

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 Loans04:07 Challenges in Student Loan Management05:58 Summer's Approach to Solving Student Loan Issues10:48 Employer Benefits and Financial Wellness14:45 Navigating Regulatory Changes17:37 Product Management Insights20:09 Proactive Messaging and Customer Experience29:06 Hiring and Team Building This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

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 RennieListen 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.Timeline00:12 Starting the Business Journey00:28 Personal Reflections and Challenges01:01 The Importance of Systems and Design01:25 Balancing Personal Life and Work02:45 Discussing the New Book03:03 Exploring the Creativity Gap07:07 Systemic Design and Environmental Impact17:31 The Role of AI in Creativity and Work27:04 Exploring Human-Centered Design27:37 AI Tools for Enhanced Productivity31:25 Transition Design and Future Innovations34:33 Creative Confidence and Overcoming Fear35:46 Personal Stories of Creativity and Bravery46:07 The Importance of Meaningful Work This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

“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 MayanListen 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 systemsListen 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

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.comActionable Takeaways✅ Bridging the Gap Between Customers and Companies✅ Empowering Customers to Become Advocates✅ The Power of Relational Customer EngagementTime Stamps02:45 An Introduction to Jake and His Journey in Community Development06:22 Bridging the Gap Between Customers and Companies13:10 Apple Community Insights18:08 Operationalizing Community Feedback27:45 Community-Driven Product Development37:00 Challenges and Strategies in Community Engagement46:30 Understanding Developer Needs Beyond the SDK57:50 The Importance of Honest Communication1:06:20 Creating Shared Success in Communities1:15:05 The Power of Relational Customer Engagement1:25:15 Final Thoughts and How to Get StartedBridging the Gap Between Customers and Companies"My work has always had some connection to bridging the gap between customer and company."—Jake McKeeJake 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 McKeeJake 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 McKeeJake 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com