The Way of Product with Caden Damiano

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

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 SukhaActionable TakeawaysBreak Down Big Tasks: Flow Gets Unlocked by Tackling a Manageable Chunk of WorkSteven 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 PuriTakeaway: 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 decadesSteven 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 PuriTakeaway: 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 CreativitySteven 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 PuriTakeaway: 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 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!Today’s guest is Thomas Payet, one of the co-founders of MeiliSearch, an open-source AI-enhanced Search API that is plug-and-play and can be deployed in just a matter of minutes. Smart presets let you start searching through your data with zero configuration.Thomas explained how focusing on simplicity and accessibility in their search API aligns with their mission to empower developers and enhance user experience across applications. Our discussion also touched on the value of the collective vision of the founding team in building a successful tech company.Connect with Thomas on Linkedin.Listen now on Apple and Spotify.𝗠𝗲𝗶𝗹𝗶𝗦𝗲𝗮𝗿𝗰𝗵 𝗙𝗲𝗮𝘁𝘂𝗿𝗲𝘀: * Out-of-the-box search experience that reduces integration time and complexity.* Intuitive design that allows developers to enhance search capabilities without extensive customization, seamlessly.* How Meilisearch is a perfect example of the commoditization of most table-stakes functionality in software. * Why create your search algorithm when you can buy one from MeiliSearch? * Why should you worry about developing yet another technical solution for collaborative docs when other companies have solved that problem already? https://www.meilisearch.com/𝗔𝗱𝗱𝗶𝘁𝗶𝗼𝗻𝗮𝗹 𝗜𝗻𝘀𝗶𝗴𝗵𝘁𝘀 𝗳𝗿𝗼𝗺 𝗧𝗵𝗼𝗺𝗮𝘀: * The importance of the team's health in building the product lies in focusing on creating something bigger than yourself. * How an open-source model fosters community-driven growth and accessibility in technology. * Insights on scaling a company effectively while maintaining a focus on developer experience.Actionable TakeawaysTable of contents01:46 The Myth of the Lone Genius03:01 Building a Company: Team Dynamics and Realizations07:03 Journey to Open Source Search API09:23 Developer Experience and API Design20:05 The Role of AI in Development23:14 Challenges and Future of AI in Development31:18 Final Thoughts and Contact Information1. Embrace the Power of Teamwork"How can we build, as a team, something bigger than the sum of us?"Thomas PayetThomas emphasized that his goal with building a company is to make something that can outlast the original founding team. Success is multiple generations of teams that continue to work on the business that the founding team initially started. A successful company typically involves a founder willing to make something bigger than themselves and focus their efforts on recruiting, retaining, and building a high-performing culture of individuals who can work together in the same direction. Takeaway: For me, it's realizing that you are most impactful when everybody on the team is doing their best work. It may be easy to play hero ball and fill in the gaps in a start-up, but truly successful companies with thousands of employees require operational and management skills to support their culture. It makes me think about Jamie Tartt in the Apple TV show “Ted Lasso”. At the start of the show, Jamie was a talented, young player who didn't see himself as part of the team, but thought that his contributions were the sole reason they won games. If you haven't seen the show, I recommend watching it. I believe it has many parallels with professional corporate life. You could be a rock star individual contributor, but until you learn how to play your role in the larger team, it doesn't matter how many goals you score. If the team itself isn't winning, then your stats don't matter. 4. Cultivate a Developer-Friendly Environment"You want developers to be impressed and feel that they can be powerful using your tool……So you can configure the search API for example, you can, push, fake data into MeiliSearch’s search."Thomas PayetThomas emphasized the importance of designing APIs that are not only functional but also a pleasure to use. A good user experience in APIs can significantly improve developer productivity and adoption rates. MeiliSearch is a developer tool, but the same lesson applies to any customer using your software. You have to make it feel like they're putting on the Iron Man suit, and you're augmenting their ability to do their job. Takeaway: Specifically for the developer experience, if your Saas business is infrastructure and technology that devs can implement into their products, making sure that they have a great experience to quickly test out and play around with your APIs, be it through documentation or interactive demos on your documentation website, will go a long way in increasing conversions and usage of your API tool. 3. Democratizing Technology Through Open Source"We did not realize how powerful it could be to make it open source."Thomas PayetGoing open source wasn't just a technical decision but a strategic move to make innovation accessible. Takeaway: Allowing developers worldwide to access and contribute to the platform accelerates growth and engagement. For me, when creating an infrastructure product, like a search API, and your primary customer is a developer, allowing them to contribute to the codebase is a great marketing strategy. Listen to the full episode to gain all the context and additional insights not included in this summary. Connect with Thomas on Linkedin.Listen now on Apple and Spotify.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

Hey Listener!Today’s podcast guest is Marcelo Calbucci, the author of "The PRFAQ Framework." Listen now on Apple and SpotifyLike many product people, I've read "Working Backwards," "The Everything Store," and even attempted to write strategy narratives using the Press Release-Frequently Asked Questions (PRFAQ) Framework to capture lightning in a bottle like Amazon without much success. Before this interview, I thought you could only do PRFAQs if you were at a company like Amazon. Marcelo is a seasoned tech leader with over 25 years of product leadership experience in major companies like Microsoft and Amazon. Marcelo has led engineering, product, UX, and data teams, drawing from his rich background to discuss the intricacies of Amazon’s Press Release and Frequently Asked Questions (PRFAQ) writing framework and how it can be adapted beyond its Amazon Culture.Marcelo noticed my story throughout the industry. Although books discuss Amazon's strategic narrative process, none provide a tactical breakdown of implementing the framework or formating your PRFAQs to achieve the best results. "The PRFAQ Framework" explores how the PRFAQ can be adapted for non-Amazon environments. It provides innovators a structured way to achieve groundbreaking goals without Jeff Bezos as their boss. Exclusively for podcast listeners and newsletter subscribers, Marcelo has provided me with a link that offers a discount to get your own copy of the “PRFAQ framework.” Get a 20% discount on the PDF Edition with the code CADEN20 on www.theprfaq.com/buy"Connect with Marcelo on LinkedInActionable Takeaways✅ The P-R-F-A-Q framework: A tool for innovation beyond Amazon.✅ Emphasizing the power of writing to drive critical thinking and innovation.✅ Recognizing the importance of testing assumptions and hypotheses thoroughly.Time Stamps02:10 Marcelo's Journey: From Small Startups to Big Tech05:50 Adapting Amazon's Written Narrative Framework for Everyone to Use11:34 The Power of Writing for Problem Solving15:10 Using Big Ideas in Small Businesses20:22 Writing for Smart Decisions28:06 Fixing Mistakes Through Practice32:44 Making a Strong Innovation Culture36:18 Deciding Which Tech Projects Are Valuable41:10 Final Thoughts and How to Connect with MarceloThe P-R-F-A-Q Framework: A Tool for Innovation Beyond Amazon"The PRFAQ framework is meant to encourage deep, strategic thinking about potential innovations, helping to filter out what might not work early in the process."—Marcelo CalbucciMarcelo Calbucci's framework transforms how teams develop ideas and make strategic decisions. A PRFAQ is a 4-6 page narrative document that helps you think critically, articulate clearly, and inspire action.Structure BasicsThe document includes a one-page Press Release (written as if your future product exists today), followed by Customer FAQs and Internal FAQs. This structure forces clarity about who your customer is, what problem you're solving, and how you'll deliver value.Writing ApproachWrite with precision. Replace vague terms like "many customers" with specific numbers. Use active voice. Avoid jargon and unexplained acronyms. Present concrete data instead of generalizations. This clarity builds trust and reveals gaps in your thinking.Collaboration TipsDesignate one PRFAQ owner who controls the document, but gather input from diverse perspectives. Hold structured review sessions with built-in silent reading time. Listen to feedback with an open mind - you're seeking truth, not validation.What Makes It WorkThe PRFAQ helps you discover what you don't know. By writing about a future state in the present tense, you identify assumptions that need testing. The document evolves through iterations, becoming stronger as more perspectives shape it.The power of this method isn't just in the finished document it's in how the process transforms your thinking and aligns your team around a shared vision worth pursuing.Takeaway: The framework helps innovators articulate clear, strategic objectives, enabling thorough pre-execution evaluation, which is crucial for decision-making. It's important that there isn't a documented author in the document. The goal isn't to take credit but to seek truth through using this collaborative artifact as a framework. Emphasizing the Power of Writing to Drive Critical Thinking and Innovation"Writing helps in thinking critically and articulating ideas more clearly. It's a powerful exercise to drive innovation."—Marcelo CalbucciMarcelo discusses the three superpowers of writing: it forces critical thinking, improves articulation, and inspires collaboration. Unlike slide decks, which often rely on visuals, narratives push you to engage deeply with your concepts, offering a clear understanding and direction.Takeaway: Writing should be an integral part of strategic planning as it refines thinking and strengthens the clarity of your ideas. Writing also unlocks what Daniel Kahneman calls "slow thinking," which forces your brain to stress every articulated idea. This is critical for big strategic bets—you don't want to be spending millions of dollars on assumptions and biases. Recognizing the Importance of Testing Assumptions and Hypotheses Thoroughly"Most P-R-F-A-Q efforts lead to a decision not to proceed, which is a valuable outcome in itself."—Marcelo CalbucciIn exploring the P-R-F-A-Q process, Marcelo reveals that most efforts conclude with a “no-go” decision. This rigorous scrutiny is intended to refine ideas by eliminating those that do not stand up to thorough investigation.Takeaway: Resilience in product management and innovation often comes from recognizing when not to proceed with a project, saving resources, and aligning focus on more promising opportunities.Listen to the full episode to discover how to leverage narrative-based planning tools to enhance your strategic impact. Then, use the link below to get your copy of Marcelo's book. I read it before releasing this episode, and it's been highly influential on my personal writing style. Connect with Marcelo on LinkedInListen now on Apple and SpotifyExclusively for podcast listeners and newsletter subscribers, Marcelo has provided me with a link that offers a discount to get your own copy of the “PRFAQ framework.” Get a 20% discount on the PDF Edition with the code CADEN20 on www.theprfaq.com/buy" 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

Today’s guest is John Tarnoff, a former film studio executive turned executive and career transition coach.Transitioning from a corporate film executive to a career coach, John has spent over a decade sharing insights and strategies to help individuals better uniquely position themselves, curate their messaging, and land roles tailored to their unique skills and strengths.He also helps individuals transition into a different career track, and in this episode, we discuss how to make a successful career transition.His unique approach draws heavily on entertainment industry metaphors, which I've been talking about for a while as a great analogy of a career in tech, where a lot of success comes from leveraging your relationships.You can connect with John on LinkedIn or visit his website at johntarnoff.comListen now on Apple or SpotifyTime Stamps02:00 Networking and Career Transitions12:30 The Role of LinkedIn in Modern Careers23:15 Strategies for Standing Out in Job Interviews32:40 Building Relationships and Thought Leadership40:05 Embracing AI and Originality in Your Work51:45 Final Thoughts and Career Development AdviceActionable TakeawaysNetworking and Career Transitions: Handling a Career Pivot"What I've discovered is that the rest of the world has become like entertainment, where it is all about networking."—John TarnoffJohn highlights that navigating through career ups and downs requires a strong network.This now applies to all industries, not just entertainment. The message is to avoid being a "supplicant" in the job market and to leverage your strengths comprehensively on platforms like LinkedIn.Takeaway: One thing I've observed in the age of AI is that data is no longer the oil; it's a judgment. Very soon, knowing a skill isn't going to be enough to hold down a job. Your reputation and trust with the people you work with will provide you with more career opportunities.Resumes are Irrelevant: How to Use LinkedIn in a Modern Career"My philosophy is that you have to make LinkedIn your master resume."—John TarnoffJohn stresses the importance of crafting a LinkedIn profile that isn't just a digital copy of your resume.Instead, it should serve as a master document showcasing who you are, your values, and the unique qualities you bring to the table.Takeaway: All strategy is just segmentation and positioning. Your LinkedIn should filter away potential job prospects by highlighting your values.If you're not attracting work through an authentic LinkedIn portfolio, you might want to reconsider the market segment you're targeting for your LinkedIn profile.Strategies for Standing Out in Job Interviews"The goal is to present an option, a set of choices, and not necessarily to get the part."—John TarnoffThe podcast explores the parallel between auditions for actors and job interviews for professionals. It’s about participating in a conversation to find mutual fit rather than desperately vying for a role.Takeaway: Use interviews as opportunities to demonstrate how you can help solve the potential employer's problems, showcasing your unique perspective.Building Relationships and Thought Leadership"It's not just having a good LinkedIn. You need to demonstrate thought leadership."—John TarnoffDeveloping a personal brand and thought leadership through consistent engagement is pivotal. It’s about positioning yourself as a professional with a unique point of view and using platforms to share insights that reflect your expertise and interests.Takeaway: My first big job at a college came from using this strategy: Engage regularly on platforms like LinkedIn. Contribute thoughtfully to discussions, publish content, and participate in community events to build your professional reputation.Embracing AI and Originality in Your Work"You have to double down on being more original, nuanced, smarter, more relevant."—John TarnoffAs AI becomes more integrated into professional landscapes, John discusses the importance of maintaining authenticity in your outputs and interactions. Use AI as a tool, but don’t let it overshadow your unique contributions and voice.Takeaway: Authenticity in your work will differentiate you in a landscape where AI can generate content at scale. Strive for original thought and genuine human connection.Thanks again for reading. If you liked this episode, connect with John on LinkedIn or visit his website at johntarnoff.comListen to the full episode to hear the great behind-the-scenes stories behind these takeaways in the context that John added to make this advice more valuable.Listen now on Apple or SpotifyHave a good one!-Caden 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!AI isn't going to take your job, people using AI will take your job. That's because disruptive technology redefines a task and workflow; it doesn't replace the responsibility behind the task in the first place. Adapting and upskilling is how you stay relevant when people are looking for folks to manage and design their products. In this episode, I discussed agentic AI with Anshul Gupta, a Product leader at Ema Unlimited. At Ema, he spearheads the development of cutting-edge agentic AI technologies to power the universal AI employee. With over a decade of experience in technology leadership, Anshul has served as Director of Product at Greenlight and as Product Lead for Google Nest and other Google teams. He holds an MBA from Yale University and earned his bachelor’s degree from the Indian Institute of Technology Delhi.Anshul shared his experiences and insights into leveraging AI to drive business efficiency and innovation. He discussed the evolution of SaaS tools, the integration of AI agents, and the shift towards more outcome-based pricing models.Connect with Anshul on LinkedIn.Listen now on Apple and Spotify.Time Stamps03:05 Anshul’s Career Path: From Lehman Brothers to Ema10:45 Leveraging AI for Business Processes at Ema17:30 The Challenges and Opportunities in SaaS Evolution25:15 Impact of AI on Customer Support and Efficiency30:39 The Future of Enterprise Tools with Agentic AI35:00 Building Trust in Automation with Human in the Loop42:48 Cost-Effectiveness in AI-Driven Workflows47:22 Cultivating Innovation in AI Product DevelopmentActionable Takeaways✅ Embracing AI for Business Process Automation.✅ Understanding SaaS Evolution and AI Integration.✅ The Power of Outcome-Based Pricing Models.Embracing AI for Business Process Automation"Agentic AI is not about replacing jobs, but augmenting capacity."—Anshul GuptaAnshul emphasizes AI's role in enhancing productivity amidst reducing team sizes and scarce human resources in industries like healthcare. AI not only aids in customer support but also facilitates complex tasks, allowing employees to focus on high-impact work.Takeaway: Utilize AI to free up valuable human resources for more strategic tasks and optimize operations across various sectors.Understanding SaaS Evolution and AI Integration"AI agents can help bridge the gaps between different tools, eliminating data silos."—Anshul GuptaThe proliferation of SaaS tools has led to operational inefficiencies due to a lack of integration. Anshul's work at Ema focuses on using AI agents to connect disparate tools, improving workflow automation, and reducing reliance on human intermediaries.Takeaway: Integrate AI agents to streamline processes and enhance business efficiency by eliminating data silos.The Power of Outcome-Based Pricing Models"The landscape of SaaS will change with more companies moving towards outcome-based pricing."—Anshul GuptaAnshul explains how Ema and similarly forward-thinking companies are shifting from traditional per-seat software licensing models to pricing based on task outcomes, offering more financial alignment and incentives for businesses.Takeaway: Consider adopting outcome-based pricing models to better align software costs with value and return on investment.Listen to the full episode to get all the insights and learn how AI is reshaping the future of business automation.Connect with Anshul on LinkedIn.Listen now on Apple and Spotify. 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!In this episode, we’re hanging out with Sagar Batchu, the guy behind Speakeasy, who’s doing groundbreaking stuff in the world of APIs and AI. Sagar’s journey from physics to tech is packed with insights into how we can all use APIs and AI to make life a little easier for product teams. Connect with Sagar on Linkedin.Listen now on Apple and SpotifyWith his background in developer tools from his time at LiveRamp, Sagar knows the drill for streamlining processes. His company, Speakeasy, aims to make APIs more accessible and user-friendly, removing the headache from the tech side. I was struck by how he sees APIs and AI weaving together to create super straightforward solutions, and I’m stoked to share some of these ideas with you.Actionable TakeawaysShoot for the 80/20 Win: "You can never perfectly solve a customer's problem... What you can do is build something that's amazing in the 80/20, right? Help 80 percent of users do things really well." -Sagar BatchuInstead of trying to be all things to everyone, focus on delivering great experiences for the majority. It’s about hitting the sweet spot between effort and impact. Robust API development helps you build this 80% foundational use case for tech products. APIs: Your Secret Weapon:"An API is like a super powerful developer, right? You're delegating some massive amount of work to a single, single URL, single call." -Sagar BatchuThink of APIs as levers that handle the heavy lifting, letting you zero in on what counts: delivering on customer promises. Let AI Bridge the Gap: "We're getting to the next level, all you need is natural language.  Tomorrow is here already…Pull up your chat window of your favorite AI product, the LLM, and say, find me the best fights to Europe” -Sagar BatchuLarge language models are making it even easier for non-technical people to leverage the power of APIs. ChatGPT and similar interfaces provide an easy way to interact with APIs using natural language. They can query specific APIs, such as those for flight information or Google search results. This capability allows you to ask ChatGPT to guide you through setting up an API for your product, potentially saving development time.Thanks again for reading this week’s newsletter.If you’re curious about diving deeper, listen to the full episode. And learn more about Speakeasy here: www.speakeasy.comConnect with Sagar on Linkedin.Listen now on Apple and SpotifyCheers,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

Hey Listener!In the latest episode of Way of Product, I had the pleasure of chatting with Rob Walling, a serial SaaS entrepreneur, author, and SaaS investor at Tinyseed. Rob spends most of his time teaching people how to build million-dollar startups without venture capital. He also helps SaaS founders build incredible businesses. Rob has started six companies, written five books, Invested in 200+ startups, and has 15M+ podcast downloads on his podcast, Startups for the Rest of Us.Rob challenges the conventional narrative that startups must raise funding, instead advocating for bootstrapping as a viable path to success. He shares his 'one-nine ninety' rule, arguing that only a small percentage of startups should pursue venture capital. Rob draws on his journey as a successful tech entrepreneur who bootstrapped multiple companies, including Drip, which he sold in 2016.Connect with Rob on Linkedin.Listen now on Apple and Spotify.Actionable Takeaways✅ Challenging the startup venture funding narrative.✅ Profit over growth—choose freedom.✅ Building resilience through hard decisions and luck.Time Stamps02:57 Real Estate vs. Software: Finding the Right Path05:39 The Value of Bootstrapping10:37 The Role of Developers in Startups17:29 The Success of Drip19:25 Making Hard Decisions with Incomplete Information19:36 Launching and Finding Product-Market Fit19:58 The Importance of Timing and Luck22:39 Building an Audience and Brand24:00 The Role of Hard Work, Luck, and Skill27:28 Challenges in Product Management33:22 The Value of Ownership and Decision Making35:12 Final Thoughts and How to ConnectChallenging the Startup Funding Narrative"There's this b******t narrative that everybody who does a startup has to raise funding. It's just not true."—Rob WallingRob argues that it’s a myth that startups must always raise funding. His "one nine 90" rule suggests that only 1% of startups should consider raising venture capital while the majority could bootstrap successfully.Takeaway: Evaluate if external funding aligns with your startup goals or if bootstrapping might give you more freedom and control.Profit Over Growth—Choose Freedom"I haven't done anything for the money. I've done it all for the freedom."—Rob WallingRob shared personal experiences, highlighting his journey from real estate investing to SaaS entrepreneurship. He emphasized that his drive was not to amass wealth but to gain control over his projects and time. Real estate investing might be good for building assets and wealth, but it is terrible when you want freedom and choice in how you spend your time. Takeaway: Focus on building businesses that align with your values and lifestyle. SaaS is a great asset class if you value freedom and autonomy. An interesting takeaway is that you only need $4M in liquid assets when you retire to live a comfortable life and not have to work again. The game isn't to amass as much money as possible; it's to figure out what enough is for you and develop that muscle of knowing when you could stop. Building Resilience through Hard Decisions and Luck"As a founder, your job is to make hard decisions with incomplete information."—Rob WallingWalling asserts that hard work, luck, and skill are vital to entrepreneurial success. Success isn't guaranteed. That's the trade-off of going into the entrepreneurial journey. Considering that there's luck involved allows you to start making decisions that put you in a position to be lucky. Jason Fried, co-founder of Basecamp, told Rob that luck and timing were essential to the company's success. Given the competitive market, Launching Basecamp now would be more difficult. Takeaway: Accept that uncertainty is part of the journey. Use it to build resilience and trust in your decision-making abilities. Strategy is just positioning and segmentation. If you can get positioning and segmentation right (the “skill” aspect of success), you might have a better chance of being lucky and winning in that market segment. ConclusionRob Walling’s journey offers a fresh perspective on entrepreneurship, emphasizing freedom, autonomy, and the importance of resilience over long time horizons. Listen to the full episode to get all the context and stories behind these actionable takeaways. Thanks for reading The Way of Product! Subscribe for free to receive new posts and support my 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

Hey Listener! If you’re serious about mastering the art of product pricing in the B2B SaaS realm, buckle up—this interview is filled with knowledge you can't afford to miss. (Pretty good pricing, dad joke, huh?)In this episode, I chat with Bill Wilson, Pricing Coach and founder of Pace Pricing. Wilson has over 25 years of software expertise and specializes in pricing strategy and tactics for his coaching clients.Connect with Bill on Linkedin.Listen now on Apple and Spotify.Key Mistakes in SAAS PricingBill framed a crucial premise: Pricing is dynamic and rooted in market changes and customer perceptions. He pointed out the fear many have of changing pricing models due to confidence issues. Bill stresses that pricing isn't static, and it’s essential to periodically review and adjust it to reflect the growing value of your product.* Misunderstanding Market Dynamics* Pricing is a Negotiation* Table-stakes features aren’t enough to justify the purchase* Founders Delegating Sales Calls Too Soon* Not Willing to “Hill Climb”Time Stamps00:00 Introduction to Pricing Challenges03:07 Deep Dive into SaaS Pricing05:54 Common Pricing Mistakes and Anti-Patterns08:55 Understanding Customer Value and Competitor Pricing13:07 Monetization Strategies and Feature Valuation16:55 Pre-Sales and Customer Engagement18:07 The Importance of Customer Surveys18:46 Leveraging Data for Product Development20:22 Insights from MIT Sloan Executive Education20:47 Understanding Pricing Strategies22:58 The Role of Product Managers in Pricing27:27 Founder-Led Sales and Founder-Led Product Management29:25 Capturing Market Demand32:04 The Multifaceted Role of Product Managers36:30 Final Thoughts and How to Connect1. Misunderstanding Market DynamicsAccording to Bill, here’s what often goes awry:* Guessing the Price: Too many businesses set prices based on intuition rather than data. Bill argues the right question is not "How much should I charge?" but rather, "How do I charge?"* Ignoring Competitors’ Shortcomings: Copying competitors can be misleading. Understanding your unique value—and then pricing for that, rather than mimicking competitor pricing blindly is essential.2. Pricing is a Negotiation"People just don't change their pricing regularly enough… I think one of the biggest mistakes is that people just don't change their pricing regularly enough. Like they don't, they don't look at it. They don't, you know, raise the price. People are scared to death to raise prices or even change their model…Takeaway: Approach pricing like a negotiation. Keep making higher-priced offers, then regularly iterate your pricing strategy as your product and market evolve. This experimental mindset will help you capture actual product value over time.3. Table-stakes features aren’t enough to justify the purchaseUnderstanding and articulating your product’s differentiated value is paramount."Understanding what value you're bringing to your customer is probably the most important thing you can do……pricing is about confidence… what value you're bringing to your customer is the most important thing you can do. It's constantly changing because the market's changing. People's perceptions are changing…… Why do you exist? You have the same price and claim to solve the same problem. What's the point?”Takeaway: Consider what's valuable to your customers by examining what you can do that a competitor cannot. Reflect on how markets and perceptions shift, and stay proactive in aligning your pricing. In many ways, pricing is about optics rather than being the most comprehensive product. 3. Founders Delegating Sales Calls Too SoonBill’s journey from software development to founding Pace Pricing underscores the importance of adaptability. He highlights how his ventures shaped his understanding of pricing and product value, with each role honing his approach to monetization.Founder-Led Sales: Bill emphasizes that founders typically excel at leading sales and product decisions in the early stages because they have an innate understanding and passion for their creations.“I’m a big fan of founder-led sales, especially at the beginning. I made the mistake of hiring a sales guy a few months after launching our product, and it was a disaster. He relocated, and we were still experimenting. It didn’t work. Building a Confident Proposition: Bill’s stories of creating a product led to monetizing solutions that genuinely solved customer problems—his narrative serves as a roadmap for budding entrepreneurs or those in product management.The founding team should run product because they can make necessary decisions. Product managers can’t do it in the same way; they may feel obligated to protect their jobs. As a founder, you can make bold decisions that might not seem sensible at the moment, but you believe they are the right moves to steer the company.”4. Not Willing to “Hill Climb”One way to figure out willingness to pay is to use a simple technique called hill climbing. Set your price for a small product and, every five to ten sales, increase the price. Keep doing this until you receive pushback, with around 20 to 30 percent of people saying no. At that point, you may have identified the maximum willingness to pay.Takeaway: Bill highlights the essential interplay between product and monetization, a concept every product team should integrate into its workflow.If you'd like to learn more about pricing strategies directly from Bill, connect with him on LinkedIn and watch his informative pricing page tear-down videos for more hands-on insights.Also, we only scratched the surface of the value of this episode. Make sure to listen to the full interview when you get a chance. Listen now on Apple and Spotify.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

Hey Listener!Most businesses think innovation is budget-bound. But it's not.In this episode, I talk about how to stay ahead of the curve with AI with Michael Todasco.At PayPal, he led a product innovation practice, exploring cutting-edge technologies long before they became mainstream. Recently, he's turned his focus to AI, becoming a key voice in the space through writing and advising.Connect with Mike on Linkedin.Listen now on Apple and Spotify.Actionable Takeaways1. "If you're not failing, then you're not trying hard enough."Understanding that failure is just part of the process is crucial in any innovative field. Mike emphasizes that his most memorable and educational career experiences stem from failures, which provide valuable learning opportunities that successes rarely do.Takeaway: Embrace failure. Each setback offers lessons that drive growth and lead to more significant innovations.2. "All ideas are born from other things."True Innovation Occurs When Ideas Intersect: Mike reminds us that unique ideas rarely emerge from a single source. Most innovations result from combining existing ideas, contexts, and inspirations. This concept reflects how diverse experiences and knowledge contribute to breakthrough innovations.Takeaway: Encourage cross-industry learning and collaboration. Draw inspiration from unrelated fields to spark creativity.3."Find where there is passion and you will learn so much from that."Mike believes that innovating successfully relies on passion—it's the force that sustains and inspires us in our work. It's not just about loving your project; it's about loving the problem enough to pursue a solution relentlessly.Takeaway: Cultivate and nurture your passion. Let it guide your efforts and keep you motivated through challenges.4. "Your future as a product manager is to be a director of AI Agents."With AI's capabilities expanding rapidly, professionals must become directors of these technological tools. The responsibility lies in leveraging AI to execute mundane tasks efficiently, freeing time to focus on strategic and creative aspects of their roles.Takeaway: Embrace AI as an ally that can augment your capabilities, not replace them. Continuously explore how it can elevate your role and responsibilities.5. "Literally give 20 bucks to Anthropic, buy Claude, give 20 bucks to OpenAI, buy ChatGPT."Get ahead of the curve by starting to play with AI today. Mike highlights the accessibility of AI tools and encourages everyone to dive in. He believes that hands-on experimentation is the best way to understand the potential and limitations of AI.Takeaway: Begin experimenting with AI tools regardless of your technical background. Test their capabilities and see how they can integrate into your workflow.Don't miss out on hearing Mike's detailed tactics and insights firsthand by listening to the full episode.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

Hey Listener!How does an AI-powered business make money? What do they do differently? In this episode, Elizabeth Samara-Rubio from SiMa.ai, gives us a practical guide to the “Business of AI” and the implications of integrating AI into real-world processes like manufacturing and agriculture.Her experience spans significant roles, including leading over 20 AI services at AWS and pioneering efforts in generative AI. Elizabeth's career trajectory also includes serving as Managing Director at Accenture, where she spearheaded growth initiatives in cutting-edge technology sectors—experiences that established her deep-seated expertise in bringing technological advancements to traditional business sectors.I was blown away by how deep Elizabeth was willing to go in this interview. I learned so much about the practical logistics of implementing AI into a business, and you won't hear this level of practicality in most AI interviews. Actionable TakeawaysTable of Contents1. Understand AI's Role in Business: “How do you make money?”2. Empower Your Ecosystem: “Intro to Edge Machine Learning Systems”3. Embrace the Maturity Curve: “The Required Time Horizon to Implement AI”4. Responsibility in AI Implementations: “Are you willing to invest and nurture this for at least 10 years?”Understand AI's Role in Business"AI is not just a shortcut. It takes time and maturity to understand where it adds value." Elizabeth Samara-RubioBy viewing AI as a long-term investment rather than an instant solution, businesses can gradually integrate AI to improve operations.Takeaway: Consider AI a marriage; you're in it for the long haul. Evaluate where it can add value to transform business processes over time.Empower Your Ecosystem "We don't just say, 'Come back when you're ready.' We're here to help build your ecosystem, You can do the most great things in the world, but if you don't have a data pipeline, you don't have a governance structure, you don't have the skill set… You can talk about it.  You can proof of concept it over and over again, but you're not going… to scale."Elizabeth Samara-RubioSiMa.ai develops AI computing hardware to be embedded into their client's systems. So that traditional businesses can start building their AI capabilities in-house. Most traditional businesses, like manufacturers and agriculture, don't have the talent or capabilities to develop their own AI from scratch. More and more, you have to consider partnering with companies that can grow with you and give you the base capabilities to develop AI in business. Takeaway: Integrating AI into a traditional business is as much a hardware problem as an AI problem. So, investing in strategic partnerships to empower your tech ecosystem will future-proof your AI implementations.Embrace the Maturity Curve“We don't just say, 'Come back when you're ready.' We're here to help build your ecosystem."Elizabeth Samara-RubioThe most significant gap preventing traditional industries from embracing new AI tech is hiring in-house talent. It's difficult to get a Silicon Valley engineer to want to work for a traditional manufacturing business in the Midwest. Companies like SiMa.ai provide services to integrate their expertise and hardware so their clients never have to develop robust AI talent in-house. Elizabeth notes the stages businesses undergo with AI integration, from increasing throughput to enhancing productivity, and the role AI infrastructure businesses will play moving forward. Takeaway: Map out the stages of AI integration in your business. Start small and scale as your team's maturity and understanding of technology grow.Responsibility in AI Implementations"An AI model demands continuous monitoring and retraining; Responsibility isn't just about deployment; it's about ensuring models operate reliably and ethically throughout their lifecycle.”Elizabeth Samara-RubioTakeaway: Develop a robust framework to manage AI models, monitor their performance, and update them as required.Listen to the full episode to get more details on-premises AI computer hardware and the in-depth technical details of how you get AI into manufacturing and agriculture. 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

Hey Listener,In this interview with Anuj Jhunjhunwala, Director of Product at Merge, we discussed how it’s easier than ever to develop API integrations between dozens of enterprise systems and how you can create a better API strategy for your products.Connect with Anuj on Linkedin.Listen now on Apple and Spotify.Modern API strategies for enterprise SAASIt's easier to take the time and money to make something custom to your business. But this isn't always cost-effective for repeatable tasks like integrating with CRMs, HR systems, and other business-critical processes that have established solutions.From Anuj's perspective, interpersonal skills and good team stewardship are the starting points of a good API roadmap. These skills play a significant role in bringing out the best in people to execute something as tricky as API integration development. Product managers, engineering leaders, and even designers must be aware of services like Merge to drive scalable and quick-to-market API integrations to HR systems and CRMs your customers need to use your product effectively. Coding and integration into Salesforce from scratch is a problem that has already been solved and could easily be a buy solution for your product. Making the switch to Product ManagementIn past episodes, I’ve been critical of the product management job family, which made me very reluctant to follow mentorship feedback that I should switch from design to product management. He provided some perspectives on my critique that evoked empathy regarding the role of product management. So, Anuj, if you are reading this, Thank you for your patience and gracefulness in addressing my concerns about this career move; this conversation was pivotal in finally making the switch earlier last year.Actionable Takeaways* The Power of Hospitality in Unblocking Success. The Virtue of Consideration. * Influence Without Authority: The One Thing Most PM’s Fail To Do—and Why* Balancing Professional and Personal Growth. How “Getting a Life” is a Growth Hack. The power of hospitality in unblocking success. "As PMs, in many ways, we are in the hospitality industry. There are different customers we serve." – Anuj Jhunjhunwala Action Tip: What does putting yourself in other people's shoes mean? It first requires you to understand your perspective. Understand why you feel a certain way about a direction.Only then can you put yourself in someone else's shoes and see how their perspective has led them to a different conclusion than yours. Finally, asking clarifying questions to reconcile your perspective and their perspective is what empathy is. Influence Without Authority: The One Thing Most PM’s Fail to Do. Every company needs someone who is talking to customers and understanding their pain points and translating that into something actionable." – Anuj Jhunjhunwala Action Tip: Work on building trust and relationships. Trust is the only currency product managers can effectively deploy in a position where they cannot exercise direct authority over business operations.Influence through inspiration rather than assertion, and create a collaborative environment where ideas can thrive.In your role as a product manager, you may not always have formal authority, yet you possess the potential to guide your team. Anuj reminded me that influence comes from inspiring and convincing others, skills he honed at work and home as a parent.Balancing Professional and Personal Growth"Paradoxically, having less time means I need to be more intentional and productive with the time I have."– Anuj JhunjhunwalaAction Tip: Balancing a high-demand role with a personal life and family can be daunting. It's led to many people delaying things like family and hobbies to build their careers. Paradoxically, not broadening your perspectives through things like having children, getting involved in the arts, and having a non-work hobby can make you less effective over the course of your career through Parkinson's law. More time leads to less urgency. Less urgency leads to lazy thinking. Having too much time leads to you filling it with work—effort that might not have needed to happen if you had some health constraints to prevent it from happening. Anuj's experiences as a young parent show the paradoxical benefit of having people outside of work who rely on him to be present and with them. It forces you to prioritize what matters most and establish clear boundaries. Now that you have a fixed amount of time to complete work, you will be forced to understand the true meaning of prioritization. You will do only the one thing that makes the most sense right now and de-prioritize everything else. 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

More than ever, we expect more from our technology.With self-driving cars from Tesla, AutoPay, and AutoSaving, as well as same-day shipments and grocery delivery, we expect our technology to think for us, not the other way around. Historically, large legacy companies have failed to make this a priority, thinking that traditional operational models and hand-holding SOPs are enough to retain the business of millennials and Gen-Z.In this episode, we discuss how American Express has reinvented itself over the past two centuries. It started as a freight forwarding company and continued to innovate with traveler's checks, credit cards, and, eventually, a strong digital technology experience. Ryan joined American Express in its next iteration of doubling down on its mobile app experience, modernizing its credit card application offering to utilize all the data available to eliminate the misleading “pre-qualification—all to cater to the new rising market of Gen Z through their “Apply with Confidence” Product.Actionable Takeaways✅ Redefining Product Management"My job is not to be right. My job is to get it right…and a lot of the product managers (are) so focused on proving their value and how good they are that they can't afford to be wrong.But the longer you go in your career, you find out that being right—out of the gate is probably the worst outcome that you can drive." - Ryan CallietPro Tip: Many failed products were based on an influential individual trying to sound smart at the cost of doing the legwork required to find the right solution and get the execution right.Even if Ryan is wrong, the first couple of attempts and the lessons learned in those failures usually give the insights needed to get it right the next time.✅ Building Trust through Being Considerate in the Design Process"Acquisition is your first experience with a brand. We want to make sure we get off on the right foot, build a trusting relationship and that you come back to us as you grow and evolve over time." - Ryan CallietPro-Tip: Ryan's user-centered design fosters transparency and trust, essential for customer relationships amid skepticism. After months of effort, their pre-qualification experience failed because customers lacked trust in it, viewing it as not a guarantee of approval from Gen Z, new to the credit card market. The team refined their plans to ensure successful approval outcomes. This challenging process required collaboration with legal, compliance, and credit bureaus. Ultimately, it resulted in strong adoption among Gen Z.✅ Taking Calculated Risks"Risk-taking is a part of this job. You can't know how people will react to a product until it’s out there. (Counting on evidence) “Beyond a reasonable doubt” is great because you have to make that judgment." - Ryan CallietPro-tip: Being data-driven 100% of the time isn't possible. Eventually, you have to make a judgment call. So, if you feel like you're at least 75 percent confident, which in the legal system is “beyond a reasonable doubt,” it's worth trying out the idea.If you're less than 75% and closer to 50%—or less than 50%, maybe it's time to take the idea back to the drawing board and continue your research until you have more confidence in another direction. 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! I just dropped a podcast episode with Dean Phillips, Head of Product Strategy at ClickUp. I enjoyed this guest so much I added a second hour of time to talk shop on product strategy.Connect with Dean on LinkedInIn this episode, we want to discuss Dean's notable journey from indy wordpress developer to leading product strategy at ClickUp and explore his unique, tailored fit role at the company.We'll also take a closer look at the company's community engagement and its impact on his current position. He shares how ClickUp tackles being an all-in-one platform without sacrificing quality and how they're using AI to make work smoother.We also chat about leading through influence—something Dean does masterfully.If you're into tech, product strategy, or just love a good career pivot story, give it a listen!Time Stamps01:43 Joining ClickUp: The Early Days18:35 From Music Side Hustles to Product Strategy24:52 The Origin Story of ClickUp33:35 Senior Leadership at ClickUp34:01 ClickUp's Contrarian Success35:13 Challenges and Innovations in All-in-One Apps38:25 Team Structure and Collaboration45:41 The Role of Obsession in Product Management54:16 Building ClickUp's Chat Tool to Replace SlackI have DOUBLE the takeaways. There is so much good stuff here.Obsession as a Catalyst for SuccessDean Phillips' path to success embodies the power of obsession. From the early days when he was just a highly engaged user of ClickUp, his unwavering dedication and deep-seated curiosity drove him to evolve into a pivotal figure in the company's strategic direction.Dean's love for creating and improving products was evident when he first pitched an idea to ClickUp's CEO. His unique insights and passion were recognized, leading to an unexpected role offer."I sent it. I was like you should execute this. Please do this. The response was “this is amazing. Do you want to come and execute it with us?"-Dean PhillipsActionable Takeaway: Let your obsession guide you. Find a problem you can't stop thinking about and immerse yourself in it. This level of engagement can be the difference between being good and becoming exceptional in your field.The Role of Intuition in Product ManagementDean describes his journey into product management as unorthodox. He relied heavily on his intuition and creative instincts, often sketching his ideas and engaging deeply with designs processes. Despite lacking formal training in product management, Dean's ability to connect dots and foresee product pathways became his strongest asset."I kind of had that intuition. But I didn't realize how to do that when I first joined. I didn't realize that is what I have to do, if that makes sense."-Dean PhillipsActionable Takeaway: Trust your intuition. Even without extensive experience, your unique perspective and insights can introduce innovation. Don't shy away from presenting your ideas—you might offer the missing piece your team needs.Strategic Innovation at ClickUpDean's role at ClickUp expanded as he took charge of aligning various product components within a cohesive strategic framework. His leadership was crucial in the development of ClickUp's integrated chat feature, which addresses the fragmented nature of workplace communications by bringing context and communication into one place."It's my role to oversee every single team, every single feature, and like stitch them all together and make sure that we're building with everything kind of coming together at the right time."-Dean PhillipsActionable Takeaway: Focus on integration. When developing strategies, ensure that your ideas foster collaboration and innovation across various components. Aligning different projects under a unified vision can significantly enhance overall productivity and user experience.Embracing the “Super Individual Contributor” RoleAn intriguing aspect of Dean's role at ClickUp is his position as a super individual contributor. He thrives on influencing without formal management authority, collaborating closely with diverse teams to drive innovation and achieve strategic goals."I'm a super IC. I'm not involved in the managerial side of things. That was by choice. I wanted to be deep into the weeds helping all the PMs and designers create things. I'm a creator."-Dean PhillipsActionable Takeaway: Embrace the super IC role by finding ways to contribute significantly without the need for direct reports. Influence and leadership can come through expertise and collaboration, rather than formal hierarchy.Overcoming Challenges through LeadershipDean acknowledges the challenges he faced as he transitioned into a leadership role, emphasizing the value of stakeholder management and influence without formal authority. This journey was not just about personal growth but also about fostering an environment where creativity and innovation could thrive." "It's my job to bring a vision together for each area that ties to the greater vision of ClickUp and where we want to go.We wanted to build a strategy which made everyone work together and we had checkpoints. A big part of how we build now with all these features is, we have different teams.-Dean PhillipsActionable Takeaway: Cultivate influence. Even without formal authority, you can lead by example and influence others through your work ethic and vision. Foster trust and communication within your team to drive collective progress.Adaptability is Key in Product Strategy"It was a big learning curve when I went to ClickUp. But once I had the title of product manager I latched onto that and dove right in to figure it all out." - Dean PhillipsAction Tip: Be open to learning and adapting in new roles. Embrace challenges and seek to quickly understand and integrate new knowledge to drive product strategy forward.Developing Contextual Solutions for Product Development"We built ClickUp chat for different kinds of people. We built it for people who love async communication and people who like async communication." - Dean PhillipsAction Tip: Tailor your product features to address varying user needs. By focusing on diverse use cases, you can create more inclusive solutions that improve user experience and engagement. 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,Here's the latest interview with Brendan Fortune, Director of Product Management at Customer.io. Connect with Brendan on Linkedin.Listen now on Apple and Spotify.In it, he shares his journey and insights into building effective product management teams and when it’s time to hire the first product manager. Brendan's Approach to Product Management:Brendan Fortune emphasizes the necessity of creating teams with the right balance of skills and passions. He advocates for the triad model consisting of a product manager, product designer, and engineer to ensure all critical areas are covered, thereby mitigating risks and accelerating growth.Actionable Takeaways💪 Understanding the role of product managers and how it ties into leadership, particularly in startup environments.🔥 The pitfalls of hiring product managers prematurely and how to determine the right timing based on product-market fit.✌️ How customer behavior can inform product flywheels and lead to sustainable growth.Risk Doesn't Need a Title Brendan discusses how risk management should not be confined to a job title but should align with the right person. Leaning into team members' strengths often results in better outcomes."I think it's on display at every startup that I've worked at. You need to be flexible and figure out how you fit into the solution.""Leaning into someone's skills and passions can lead to amazing outcomes, as the team reforms around that individual's idea."Action Tip:Encourage flexibility within your team by aligning roles with individual strengths and passions rather than strictly defined job titles.The Flywheel Concept When Deciding Team TopologiesBrendan talks about focusing on the flywheel—a sequence of customer actions and reactions—to streamline growth and optimize product management."The idea of having a clear sense of your product flywheel can guide product organization and help plan when to hire new team members."Action Tip:Identify your product's core flywheel and ensure your team is structured to facilitate its natural progression.Pitfalls of Early Product Management HiresHiring a product manager too soon can stall growth. Brendan suggests waiting until the financial metrics justify the hire, ideally outside VC funding."Can you economically support a salary for a good product manager? That's a good indicator of reaching product-market fit."Action Tip:Evaluate whether your business has generated enough value to invest in a product management hire responsibly.The Importance of Story: Creating meaningful work often hinges on the story being told. Brendan highlights how product managers can foster excitement and drive within a team by crafting a compelling narrative."People want to do meaningful work and the best product manager helps make the work feel meaningful."Action Tip:Focus on the narrative that ties your team's work to broader company goals, fostering a shared sense of purpose and clarity.Best,Caden Damianocaden@hey.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