The Way of Product with Caden Damiano

Steph Cartwright is a Job Search Strategist and Certified Professional Resume Writer (CPRW) at Off The Clock Resumes LLC, where she helps tech and industry leaders present as confident, high‑value candidates on screen. She became known for career branding that turns complex experience into clear, employer‑ready narratives that consistently convert views into interviews. She has built an audience of more than 3,200 followers and over 500 direct connections while operating from the Spokane–Coeur d’Alene region.Previously, as Founder and Principal Writer at Off The Clock Resumes LLC, she scaled a boutique career services practice into a specialized partner for job seekers navigating competitive roles with compensation packages frequently exceeding six figures. She became known for a structured, data‑driven intake process that translates into résumés and LinkedIn profiles optimized for modern applicant tracking systems, significantly increasing interview rates and offer quality for her clients. Through one‑to‑one engagements and digital products, she has supported hundreds of professionals across tech and adjacent industries.Her career highlights include earning and maintaining the CPRW credential, signaling adherence to rigorous professional standards in résumé writing and career communication. She has continued to refine a distinctive positioning around “career branding that gets noticed and lands interviews with higher offers,” focusing on clarity of story, on‑screen confidence, and repeatable systems that scale beyond any single job search. By combining structured frameworks with empathy for career pivots, she has become a trusted partner for leaders who need to articulate complex trajectories in two pages or less.Listen to episode 161 on Spotify or Apple PodcastsWhy the old keyword-stuffing playbook is dead. And what job seekers should do instead.“I am the face behind my business and in front of my business,” Steph says, “as well as the one that does all the one-on-one work with clients.” There’s something in how she phrases it—face behind and in front—that captures the exhausting clarity of solopreneurship. She’s the product and the salesperson. The expert and the marketer. And she’s been doing it since 2014.She started as a serial job seeker. “I am well rehearsed in job search practices,” she says, with the kind of dry humor that only comes from having lived through too many of them. Now she’s getting ready to attend another annual conference to stay current on hiring tech. The landscape, she tells me, is shifting faster than most people realize.I ask her what current hiring practices are doing to block talented candidates.“It’s gone beyond applicant tracking systems,” she says. “That used to be very keyword based. And now it’s not so much the worry of making sure your resume has all the right keywords.” She pauses. “AI is now adding generative and predictive analytics to this technology. It’s actually going to make it easier for job seekers because they don’t have to worry so much about the specific keywords.”This is counterintuitive. For years, the advice was: mirror the job posting. Product development. Project management. Agile methodology. Match the strings, beat the algorithm, get in front of a human. That era, Steph tells me, is ending.She walks me through an example. Say a product developer five to ten years ago wanted to tailor their resume. They’d add the term product development to ensure their resume would surface in searches. If someone went into LinkedIn looking for that skill, they’d pop up. “It was really important to have the right keywords, the right phrasing,” she says.Now? “If you don’t have the specific words—the specific product development phrase—AI is going to look at your experience and it’s going to look at context. It’s going to look at, you know, predictive. If you say you’ve done this, you likely have this skill.” She lets that land. “AI is going to start making assumptions about you that will help you.”The old systems were deterministic. You could game them if you knew the rules. The new systems are probabilistic. They infer. They read between the lines. This is good news for generalists and career changers—people whose careers don’t fit neatly into keyword buckets.I tell her this resonates. I’ve jumped between design and product management throughout my career, and I’ve gotten direct questions: What do you actually want to do? Few people accept my honest answer, which is basically whatever the company needs and I find interesting at the time.Steph nods. “At some point in the last ten years, the trend shifted from wanting someone with a broad range of skills to: we want a specialist, we want someone who really is an expert in this one thing.” She pauses. “But now that we’re adding in this AI element, we’re kind of going back to the original trend where AI wants to see the breadth of your knowledge and then be able to say, yes, this person has these skills, but they also have these skills, which will likely be a good fit.”The conversation turns to how people market themselves, and Steph lands on an analogy that sticks.“Highlighting benefits over features,” she says. “Those keywords, those skills—those were features, not the benefits. Whereas now, if you shift your mindset to: I’m going to position myself as the best fit for this job, not because of my skills, not because of the features that I bring, but because of the impact I’ve made.”She explains how this plays out technically. “One bullet on your resume can speak to an ATS based on the keywords in it—so that one bullet may be associated with project management skills. Whereas now with AI, that one bullet, depending on how much information you give it, might register five, six, seven different skills associated with that one bullet because of the impact you had.”The example she gives: designing a product that increased efficiency for a large enterprise. That single bullet, written with context, signals project planning, project management, design, strategy—multiple capabilities inferred from one outcome. The question isn’t What can you do? It’s What have you made happen?I bring up LinkedIn, and how I’ve started writing narrative case studies instead of bullet points for each role. The bet is that AI will read it and extract more context to provide better evaluations to hiring managers.Steph lights up. “Storytelling, especially on LinkedIn, is key. I used to work with clients very specifically on, let’s take these bullets on your resume and expand them as projects on your LinkedIn profile. Because that project section is also searchable. It’s also readable by the tools behind the scenes.”She leans into it. “Tell me the full story. How it started. What was the challenge that needed to be resolved. What you did, who you impacted, what obstacles you faced, and then what was the ultimate outcome.” Each project gets 2000+ characters, she says—2000 characters the AI can read, infer from, match you to opportunities.But the real shift in her thinking, she tells me, isn’t about resumes at all.“If you don’t tailor your resume for this specific job before you apply, you won’t even be considered,” she says. “I am still a strong believer in tailoring a resume if you’re gonna apply online. But now, because the competition is so high, I would say it’s more important to have a full blown strategy built outside of applying for jobs online.”What does that strategy look like?“It’s more important to be strategic in who do I need to talk to? Who can I start relationships with—even if it doesn’t result in a job at that company—but is going to expand my reach in my targeted field or industry?”She reframes networking as something that makes people less uncomfortable. “You can’t just think of it as networking—just getting your name out there and hoping something lands. But building professional friendships is what is going to make the difference.”I ask her how she coaches someone who’s just starting out, someone without an existing network.“Find a trade or professional organization that you can join and actively participate in,” she says. “One that opens you up to develop professional friendships with people you would maybe look at as competitors for different jobs, but they’re also mentors.”She tells me about a colleague halfway across the country. “She and I just sat down and had lunch together over Zoom and just talked shop. She has sent me referrals. I have sent her referrals. I would call her a mentor, but we’re also friends.” There’s warmth in it. “I know she’s in my corner. She will never do something to jeopardize that professional friendship.”I share a story from my own career. Five years ago, I had an offer from a company that I turned down for something more interesting. The hiring manager was a class act about it—That sounds really cool, I’m really excited for you—and he kept in touch. For five years. Then, recently, when I was looking again, an opening came up. I interviewed. It went well. Then a budget issue threatened to kill it. Another team needed to shuffle a designer internally. I waited all weekend, assuming it was over.The recruiter called. We want you here. We have to work this out, but we really want to figure out a way to make this work. They talked to the VPs. Got budget approval. Carved a spot out for me.“That’s best case scenario right there,” Steph says.It’s a five-year story arc, I tell her. And it only worked because the relationship was real.“That is the end goal,” she says. “You’re not going to find that by just applying for jobs on Indeed. You have to do that extra work. And the narrative of this is how you’re supposed to find a new job keeps people from trying.”She pauses. “Companies are notorious for creating roles for the people they want. If you can figure out what that company’s challenges are and how you can help them solve those challenges—that’s what’s going to help you get your foot in the door at a company y

Kasim Aslam is the Co-Founder of Pareto Talent, a boutique executive assistant recruiting agency helping entrepreneurs reclaim 40+ hours per month through rigorously trained, full-time remote EAs sourced primarily from Latin America. Rising to prominence in the 2010s as the architect behind one of the top-ranked Solutions 8 Google Ads agencies in the world, he became known for building and exiting multiple seven- and eight-figure businesses while positioning himself as a leading voice on performance marketing and founder leverage. Today he is widely regarded as an influential figure in the emerging discipline of Answer Engine Optimization and founder systems design, serving growth-focused entrepreneurs through Driven Mastermind and his briefing series The Daily Sigh.Previously, as Founder and CEO at Solutions 8, Kasim scaled what his M&A advisor described as the largest specialized Google Ads agency in the world at the time of its sale, managing more than $100M in ad spend and growing a fully remote team of over 100 employees across multiple countries. In October 2022 he executed an all-cash eight-figure exit after nearly 18 years building the firm from a one-man web-development operation into a top-ranked Google Premier Partner serving hundreds of clients. That transaction marked his third successful exit after building six different seven- and eight-figure ventures over two decades.His career highlights include co-founding Driven Mastermind, an invite-only growth community led alongside Perry Belcher and Jason Fladlien that brings together multi-seven- and eight-figure founders for high-velocity experimentation and scale. He also co-founded Nido Marketing, a specialist firm dedicated to helping Montessori schools grow enrollments through digital marketing programs and over 20 self-guided courses built for more than 100 school operators. Earlier, as Co-Host of the Perpetual Traffic Podcast, he helped keep the show consistently ranked among the top 10 marketing podcasts worldwide while publishing weekly episodes over four years to an audience of thousands of practitioners.As the author of “The 7 Critical Principles of Effective Digital Marketing,” Kasim was recognized by BookAuthority among the 100 Best Digital Marketing Books of All Time and named one of UMSL’s Top 50 Digital Marketing Thought Leaders in the United States in 2020. Through his current project The Daily Sigh at DailySigh.ai, he delivers a 15-minute daily briefing distilling what actually mattered in business, AI, and entrepreneurship for revenue-generating founders, reinforcing his legacy as a strategist who converts complex shifts into practical, founder-ready decisions.Listen on Apple Podcasts↗ and Spotify↗Why 20 years of watching “the best product lose” led to a radically different business thesis“I spent 20 years watching the best product lose,” Kasim Aslam tells me. He lets the sentence land. “I spent 20 years watching the best products go by the wayside. The best kept secret stay a secret. Because they couldn’t drive traffic.”We’re an hour into a conversation that started with him saying he builds businesses professionally—a phrase so casually delivered it took me a moment to register its weight. Kasim has built the number one ranked Google Ads agency in the world, exited to a SoftBank-backed organization at an eight-figure valuation, and accumulated a portfolio of 17 companies across digital marketing, real estate, and professional services. He’s not on the org chart of any of them. His favorite answer, he tells me, is “I don’t know.”But before any of that, there were the failures. Over a hundred of them, by his count. Medical transcription. A furniture store. Selling purified mercury. A moving company. Baskets on Amazon. “When I went back and tried to count,” he says, “I couldn’t count every epic failure.”Kasim was raised by a blind single mother on social security disability. At 22, he lost his job in the 2008 crash with $150,000 in debt. What he found on the other side of those hundred failures wasn’t a better product or a smarter strategy. It was a formula that most entrepreneurs get exactly backwards.Find the traffic first. Then figure out what problem to solve.---The insight came from a peculiar vantage point. As the founder of Solutions 8, Kasim spent years managing $100 million in advertising spend for other people. Two hundred clients. Eighty employees. He got to see everything—what things cost, what they sold for, retention rates, competitor landscapes, what attention was actually worth.“What’s really devastating when you start to wrap your head around what that means,” he says, leaning into the word, “is Google makes more money than you do. You’re slaving away and the traffic stores are eating your lunch. You’re working for them.”An e-commerce company, he explains, will spend more on traffic than on cost of goods, fulfillment, operations, and customer service. Sometimes combined. The math is brutal. And most founders only discover it after they’ve already built the thing. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

Kelly Price, SHRM-SCP is the Founder & CEO at ThriveHR, LLC. Rising to prominence in the 2010s as a high-impact HR and Total Rewards leader across multi-location service organizations, she became known for transforming people operations into a strategic growth engine for small and mid-sized businesses. Today she is widely regarded as a people-first operator who helps owners turn culture, compensation, and benefits into durable competitive advantage.Previously, as Senior People Partner – Total Rewards at nbkc bank, she led compensation and benefits strategy for a rapidly evolving financial services organization during a period of tightening labor markets and accelerated digital transformation. In her earlier tenure as People Operations & Benefits Manager at nbkc, she was responsible for end-to-end HR operations for the Kansas City metropolitan footprint, supporting several hundred employees through multi-year change while maintaining compliance, retention, and engagement metrics.Her career highlights include a seven-year rise at Samson Dental Partners, LLC, where she progressed from Recruiting Manager to Vice President of Human Resources while the organization scaled across multiple states and dozens of dental practices. During that period she built the recruiting function from scratch, hired clinical and non-clinical teams across home office and field locations, and expanded the HR organization to support rapid growth in headcount and locations. Earlier in her career, she sharpened her recruiting and talent acquisition craft at Ferrellgas and Waddell & Reed, managing nationwide and regional hiring mandates in highly competitive markets.A graduate of Kansas State University with a bachelor’s degree in Hospitality Administration and a SHRM Senior Certified Professional credential renewed through 2027, she has also been an influential figure in the Kansas City HR community through board service with Total Rewards KC and L’Arche Heartland. Through ThriveHR, she continues to advise founders and leadership teams across Kansas City, Southwest Florida, and Houston on building resilient people strategies that scale.Listen on Apple Podcasts↗ and Spotify↗The Netflix ProblemEveryone loves the Netflix talent philosophy in theory. Treat adults like adults. Pay top of market. Fire fast. No vacation tracking.But Kelly sees the gap between billion-dollar companies and the small businesses that make up most of America. A 50-person company in Kansas City can’t offer five engineers’ salaries for one rockstar. They need B players and C players for repetitive, supervised work—and that’s not a failure, it’s reality.“An A player can’t sit in every single role because they won’t be happy,” Kelly told me. “There are lots of different levels of work that needs to be done.”The talent strategy has to match the business. A startup founder passionate about their product doesn’t need—and can’t afford—Netflix-style HR. They need someone to take the compliance burden off their plate so they can focus on what they love.---Control and MoneyWhen I asked about return-to-office mandates, Kelly didn’t hedge: “It’s all about control. Control and money.”She’s watched clients cling to eight-to-five, sit-at-your-desk policies despite every study proving flexibility drives productivity. COVID revealed something we can’t unsee—life is precious, and there’s more to it than work.But that doesn’t mean 100% remote works everywhere. Some jobs require physical presence. Some small businesses can’t manage a distributed team. The mistake isn’t having people in the office—it’s treating flexibility as a perk rather than a tool.“That is 100% a people problem,” Kelly said. “Do you have leaders in place that are holding their employees accountable? Creating an environment where they can ask questions when they don’t know what to do?”The system—remote, hybrid, in-office—doesn’t determine success. Leadership does.---The Three-Tier AuditWhen Kelly onboards a new client, she starts with the business fundamentals: How do you make money? What are you trying to accomplish? What type of people work best here?Then comes the audit—every policy, every state, every compliance requirement. Hiring, I-9s, performance management, payroll, termination, offboarding. Top to bottom.The findings get prioritized into three tiers:**Compliance first.** “You’re gonna get sued for this stuff.” Fix what the government could fine you for before chasing strategy.**Tactical second.** Hiring processes, performance reviews, HR systems. Are they efficient? Are the people running them trained?**Strategic last.** Only after the foundation is solid do you ask: How can the people function support business growth?“If you don’t have these foundational things in place,” Kelly said, “you really shouldn’t be thinking about strategy.”---Ask PermissionThe most practical advice Kelly shared was disarmingly simple: ask permission.“I wanna be honest with you, and I’d like permission to share my thoughts.”She’s never had anyone say no. They might disagree afterward, but they listen. And often they come back later, having processed what was said.It works with founders, CEOs, leaders with egos—anyone who needs to hear something they don’t want to hear. The phrase reframes confrontation as collaboration. You’re not attacking. You’re partnering. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

Makoto Kern is the UX Product Strategy Design Leader at IIIMPACT, Inc.. Rising to prominence in the 2000s, he built a reputation for transforming complex enterprise software into high-adoption products, guiding clients through more than 22 years of digital transformation initiatives across energy, cybersecurity, healthcare, fintech, and logistics. He became known for driving 450% year-over-year revenue growth at IIIMPACT while helping Fortune 500 and high-growth B2B SaaS teams achieve up to 85% user adoption versus a 34% industry average, and for preventing $2.3 million in wasted spend through strategic planning workshops.Previously, as a senior UX consultant at FROM, The Digital Transformation Agency, he led mobile and responsive web experience design for one of the largest U.S. car rental companies, a major Broadway e-commerce platform, and a top payroll provider, contributing to multi-million-dollar online revenue channels between 2011 and 2020. He became known for building cross-platform loyalty workflows across iOS, Android, and responsive web, and for introducing UX strategy practices that informed product decisions through analytics and usability testing.His career highlights include senior UX roles at Walgreens and Humana, where he shaped e-commerce, mobile, and responsive experiences for millions of consumers between 2011 and 2014. At Walgreens, he helped optimize cross-channel journeys across Walgreens.com and affiliated sites, supporting year-over-year gains in online conversion for properties spanning pharmacy, beauty, and vision. At Humana, he led UX for member-facing mobile apps and loyalty programs, collaborating with innovation teams to move concepts from brainstorming to tested prototypes in an agile environment.As host and executive producer of the Make an IIIMPACT Podcast, he translates two decades of product and UX leadership into weekly conversations for CTOs and product executives, growing the show to more than 80,000 subscribers and generating over 35,000 views on individual episodes in 2024. He also writes about his journey from robotics and fuzzy controllers to software leadership in essays like his Medium piece “From Broken Glasses to Building Better Software,” extending his influence beyond client work into broader product and design circles.Listen on Apple Podcasts↗ and Spotify↗What happens when companies pause everything for eight months to integrate AI and discover nobody uses it.“The moat is the user experience,” Makoto says. “The easier you make that, the better. No one cares if you’re using Claude or ChatGPT.”We’re about twenty minutes in, and I’ve been waiting for someone to say this out loud. Everyone’s talking about AI strategy, AI integration, AI roadmaps. Makoto’s been consulting for twenty years, and he keeps coming back to the same point: nobody cares about the backend. They care if it solves their problem.Makoto Kern started as an electrical engineer in Chicago, building software for manufacturing environments. His job was to automate systems, make them faster, more efficient. But he kept noticing something. The software was built by engineers for engineers—and the people on the factory floor weren’t engineers. They had to use it anyway.“It kind of naturally led to UX,” he tells me. He started building websites on the side during the .com boom, taking sales calls over lunch at his full-time job, finding work on Craigslist. Eventually he quit and started IIIMPACT. That was twenty years ago.I ask him what’s been consistent across those two decades. What survives the hype cycles?“You still see the same problems no matter what the technology is,” he says. “You have to be hyper-focused on knowing that you’re solving someone’s problems.”The pattern is always the same. During the .com boom, companies added “.com” to their name and watched valuations spike. With crypto, the pattern repeated. Now with AI, he’s watching it again—companies pausing critical feature development to “just integrate AI,” only to discover nobody uses it.Then he tells me about a case study that stuck with me for days.One of his clients decided to pause all product development for eight months to integrate an AI chat feature. Microsoft was pushing Copilot. Salesforce was pushing Copilot. Everyone wanted one. So they built one.“Eight months later it’s integrated,” Makoto says. “We take a look at Pendo. We see a prompt, maybe two prompts during training. Nothing else after that.”I wait for him to continue.“So nobody’s using this. And this is exactly why you test.”The features users had been asking for? On the back burner for eight months. The competitors who kept building those features? Now ahead. Eight months of “innovation” became eight months of falling behind.“It’s another Clippy right now,” he says, and something in his voice suggests he’s said this before. “People are falling off after using it once or twice. They’re like, I don’t need to use this. I’m gonna go back to what I’m familiar with.”I bring up the instinct to chase technology—how hard it is to tell a board you’re focused on fundamentals when they’re asking about AI strategy.Makoto has a metaphor for this. “It’s like telling a kid it’s cold outside, wear a jacket. They don’t wanna wear the jacket.” He pauses. “Then they get sick.”He says when his team goes into consulting gigs, a lot of these companies are the kid who doesn’t want to wear the jacket. You tell them what’s good process, what’s good strategy. But they’re going to do it their way. “So we go in there. Of course, I bring the jacket. I tell ‘em to put it on after they’re cold.”There’s something resigned in how he says after.“Have you heard of the Peter Principle?” he asks.I shake my head.“You’re promoted to the point of incompetence.” He lets it sit. “You get somebody who’s a great developer and they’re promoted to manager, but they can’t manage people. So they stop there.”He’s seen product people say we don’t need to change anything, it’s working as it is. No innovation. Just following what competitors do because it’s the safe play. “If the salespeople heard about this, they’d be like, are you crazy?”The conversation turns to vibe coding—all those people on Twitter claiming software is cooked because they built something in five minutes. I tell him I’ve been using Claude Code, and it’s incredible for setup, for gluing repositories together. But when things break, I don’t understand what I’m reading.“Yeah,” he says. “That’s UX.”Performance is UX. Security is UX. If your dev team creates tech debt and every button takes five seconds to load, that’s not a backend problem. That’s the experience. And with everyone vibe-coding everything, he says, you’re going to see privacy issues, security flaws. His cybersecurity clients are ready. “They’re licking their lips.”I ask him what he does when the AI hype gets overwhelming—all the noise about automation, about making a hundred thousand dollars a week.“I just took a step back,” he says. “This is the bubble that people are going after. Don’t pay attention to that. Just stick with the fundamentals.”He tells me about his own experience with AI. He uses it for crunching data sets, for research, for brainstorming. But he sees the hallucinations. He questions the outputs. “Don’t use it as the end-all, be-all.”Near the end, I ask what hasn’t been said.“If you want to innovate, you can’t be scared about utilizing the right resources in the right way,” he says. “Because now if you don’t, it’s going to be detrimental to your company.”He pauses.“Don’t rely so much on technology. Always fall back on the right processes. If your product interfaces with users—like most of them do—be super hyper-focused on the user experience. Even if you have board members pushing your CEOs and your leaders into a certain direction, you have to get them to understand: are you solving a user’s pain point or not?”If you’re not, he says, then who knows what you’re building toward.I’ve been thinking about this conversation since we hung up. The technology changes, but the failure mode doesn’t. .com boom. Crypto. Now AI. Same mistakes, faster.The companies that survive these cycles aren’t the ones chasing features. They’re the ones who remember what the moat actually is.It’s not the AI. It’s how easy you make it for humans to accomplish what they came to do.The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

Tom Shapland is the Product Manager at LiveKit. Rising to prominence in the 2010s by turning PhD research at the University of California, Davis into a commercial irrigation analytics company, he is now helping build an open source platform for multimodal, real-time voice and video agents used in production by developers across sectors. At LiveKit, whose open source stack launched in 2020 and underpins a cloud platform serving voice, video, and physical AI agents at global scale, he focuses on productizing ultra-low-latency infrastructure into practical tools for AI builders.Previously, as CEO at Canonical AI, he built “Mixpanel for Voice AI,” an analytics platform that mapped caller journeys across thousands of Voice AI calls to show where and why agents failed, enabling developers to systematically improve conversion and reliability. Between 2023 and 2025, Canonical AI processed large volumes of agent call transcripts and latency metrics, giving Voice AI teams a single interface to debug failure paths and unlock additional call volume from enterprise customers.His career highlights include founding and serving for 9 years as Co‑founder and CEO of Tule, a Y Combinator S14 company that commercialized UC Davis research into in‑field sensors that directly measure Actual Evapotranspiration (ETa) to guide irrigation decisions. From 2014 to 2023, Tule deployed research-based hardware and software across California specialty crops, with its sensors installed in commercial vineyards and orchards to quantify field‑scale water use and crop water stress, helping growers cut irrigation water use by material percentages while maintaining yields. In January 2023, CropX Technologies acquired Tule, adding its above‑canopy sensing technology to a global precision irrigation platform operating in more than 50 countries.Rising to prominence in the 2010s as an influential figure at the intersection of agricultural science and data infrastructure, he has since translated that domain expertise into Voice AI analytics and now into real‑time multimodal agent platforms. He remains closely connected to the Y Combinator alumni ecosystem, leveraging over a decade of founder experience—from PhD research commercialization to post‑acquisition leadership—to mentor teams building the next generation of agentic AI products.Listen on Apple Podcasts↗ and Spotify↗The Most Dangerous Advantage a Founder HasMost people think that to start a company, you need experience. You want to know the pitfalls, the market dynamics, and exactly how the “game” is played. We vaunt experience as the ultimate shield against failure.But Tom Shapland, a decade-long founder turned Product Manager, fundamentally disagrees. He argues that the most important asset he had when starting his first company wasn’t his PhD or his technical expertise. It was his naivete.“The secret sauce I had is what every first-time founder has, and that is naivete,” Tom shared during our conversation. “You just don’t know how hard it’s gonna be. And you just think, oh, I can take on the world.”Here’s the thing: experience is often just a collection of reasons why something won’t work. When you’ve seen a dozen startups fail in a specific niche, you stop looking at that niche. When you know how hard it is to build a sales motion in a legacy industry like agriculture, you don’t even try. But the first-time founder doesn’t know better. They haven’t been burned by the reality of the 10-year grind, so they walk into the fire with a smile.Now, as a Product Manager at LiveKit—building the engine for the voice AI revolution—Tom brings a unique perspective. He *knows* how hard it is. He knows the luck involved. The challenge for the experienced operator is deliberately choosing to ignore those scars and find that same spirit of “delusional” confidence that made the first win possible.We often talk about “Product-Market Fit” as a destination. But looking at Tom’s journey with Tule, it’s clear that traction isn’t just a metric; it’s an unblocker. Before he had a product, he couldn’t find a co-founder. He couldn’t find investors. He couldn’t find employees. It was only when he stopped building and started pre-selling—getting farmers to sign up for a product that didn’t exist—that everything else fell into place.Traction unblocks the world. It’s the ultimate signal that your “side quest” is actually the main mission.As we move into a world where we can simply talk to our computers—where English is the new terminal—the role of the builder changes. Whether you’re a founder or a PM, the job is the same: have the clarity of thought and the naive courage to ask for what shouldn’t be possible yet.The Way of Product w/ Caden Damiano is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

Keith Lucas is a startup advisor specializing in product, growth, people, and culture who previously served as Chief Product Officer and Chief Technology Officer at Roblox, where he helped transform the platform into a global ecosystem for tens of millions of creators and players. Rising to prominence in the 2010s, he became known for building engines of innovation inside entrepreneurial teams, uniting long-term mission, values, and execution into a single operating system for high-output organizations. He is the author of Impact: How to Inspire, Align, and Amplify Innovative Teams, a 202-page playbook published in 2025 that codifies these practices for leaders across high-growth technology, gaming, and AI-driven companies.Previously, as Chief Product Officer and later Chief Technology Officer at Roblox, Lucas led the product and engineering organizations through one of the strongest multi-year growth runs in the company’s history, helping drive player and revenue expansion of roughly 300–400% year over year heading into 2016. He scaled the product organization from a single product manager and a small design and analytics group to a 30-person, data-driven team, while guiding engineering from bi-weekly releases to daily and weekly cadences across web and core client surfaces. During this period, he helped architect the platform’s shift to mobile-first growth, global game server distribution, and a more systematic approach to discovery and developer incentives, contributing to annual revenue that would later be reported in the billions of dollars as the company matured.His career highlights include serving as Chief Operating Officer at Instrumental, an AI-powered manufacturing intelligence company where he helped the business grow its customer base across consumer electronics, automotive, and medical devices as revenue expanded by an order of magnitude in the wake of its Intercept product launch. Over two decades in technology, he has held senior roles across engineering, operations, and business, from early-stage leadership at Roblox to advisory work with startups in AI, gaming, entertainment, and enterprise software, bringing a portfolio of experience that spans platform infrastructure, creator ecosystems, and go-to-market strategy. Lucas holds a Ph.D. in Aeronautics and Astronautics from Stanford University and a Master of Public Policy from the University of California, Berkeley, a combination that underpins his analytical approach to building enduring, institution-scale teams.As author of Impact: How to Inspire, Align, and Amplify Innovative Teams, he codifies a two-tier framework that helps leaders avoid stalled scaling, culture dilution, and loss of focus by treating culture as a system and leadership as a discipline. He now works directly with founders, CEOs, and executive teams as a trusted advisor, helping them design what he calls “engines of innovation” that can sustain compounding impact over decades rather than single funding cycles.Listen on SpotifyListen on Apple PodcastsInnovative teams do not stumble into great productsThey intentionally build engines of innovation in how they hire, promote, and operate day to day. Keith Lucas has seen both well run and badly run startups, and the pattern he cares about is deceptively simple: Purpose-driven companies that adopt a long-term, institution-building mindset have a structural edge over those optimized for short-term financial wins.​When Keith thinks about building entrepreneurial teams, he looks for five “non-negotiables”: * Can this person elevate the team’s ability to create, innovate, or solve problems?* Do they align with the values? Do they want the same long term outcomes?* Do they believe in the mission?* Can they live with the team’s non-negotiable principles?* Do they meet the minimum standards of mastery and autonomy?Teams that take those standards seriously quickly surface who needs too much handholding or who does not care enough about quality, because the realized culture will not support them.​Here’s a practical nugget you can take from this episode today (though I recommend you listen to the whole thing, it’s one of the best episodes on leadership)His favorite hiring and team staffing question for sussing out these non-negotiables is something I am going to steal: When you have a free moment at work, where does your mind go?The answer exposes intrinsic motivation, and great leaders use that signal to dial in roles so that enthusiasm, skill, and impact line up instead of grinding against each other.​Underneath all of this is a simple thesis: if you want an engine of innovation, you need people who behave like mission athletes—mission driven, performance oriented, continuously growing, and elevating their peers—and you need to give them aligned autonomy instead of micromanaged checklists. This episode is for builders who care about creating something enduring rather than chasing short-term wins, and who are willing to design their hiring, culture, and leadership practices to match that ambition.​ Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

Matthias Wagner is the Founder and CEO at Flux, the AI-native hardware design platform streamlining how teams build printed circuit boards and electronics at scale. Rising to prominence in the late 2010s, he became known for transforming manual, spreadsheet-driven supply chain and PCB workflows into cloud-first, collaborative systems used by distributed engineering teams worldwide.Previously, as Product Manager at Facebook (now Meta), he led the Moments App, AR ads, and Oculus VR initiatives, working on products that collectively reached hundreds of millions of users globally. During his nearly three-year tenure, he operated at the intersection of machine learning, consumer-scale experimentation, and hardware-enabled experiences, which directly informed Flux’s AI-first approach to electronics design.His career highlights include co-founding 42media group in 2004 and bootstrapping it into a multi-million-euro digital signage and media business serving enterprise clients such as IBM, McDonald’s, DHL, Volkswagen, and major German financial institutions. He also co-founded Hochzeit.de, a wedding marketplace with planning and budgeting tools that grew into a leading German platform connecting thousands of couples with venues and vendors, and he has mentored multiple startup cohorts, helping dozens of founders move from idea to growth-stage businesses.Listen on SpotifyListen on Apple PodcastsShip platforms that make hardware iteration feel like modern dev tooling.Matthias Wagner asked an Apple engineer about managing the iPhone supply chain.“What software do you use?”“What software? Cubicles full of people. Each one has a phone and a list of numbers. They call suppliers all day, updating a shared spreadsheet. One person can edit at a time.”That’s the terrain. Not what the frameworks say. Not what the business models teach. The actual terrain.Summer 2019, Matthias left Facebook to build electronics in his Oakland workshop. Got frustrated immediately. The tools hadn’t evolved since the mid-nineties. No version control, no collaboration, no automation. Just paper processes ported to Windows.The map said hardware was hard because manufacturing was expensive and inaccessible.He tested it. Ordered any semiconductor in the world to his backyard. Unit quantity: one. Seven-day turnaround from China. A few hundred dollars.The supply chain had democratized completely. The design tools hadn’t budged.At Facebook, machine learning had transformed everything. Why not here?A friend told him, “Matthias, you’ve been complaining about this all summer. Do something about it.”That’s Flux.ai. Making hardware design as accessible as software development.But here’s the pattern: most builders read the map and execute. Matthias walks the terrain and observes.The anecdotes don’t match the data. The frameworks don’t capture the friction. The best practices miss the opportunities.He doesn’t trust what frameworks say should be true. He tests what is actually true. Sources information directly. Builds messy models. Notices the friction everyone accepts as baseline.The map said hardware required massive capital and factory connections. The terrain showed the real constraint was tools nobody had fixed in thirty years.That gap between map and terrain? That’s where opportunities hide.Most product strategy happens in conference rooms. You fill out canvases and positioning statements. Run the plays from the playbook. But you’re optimizing against a map, not reality.The reality is cubicles and phone calls managing materials for the iPhone. The reality is CAD software that looks identical to 1995. The reality is sourcing spreadsheets with single-user edit locks in 2025. These aren’t exceptions. This is how things actually work.You can’t spot that from the map. You have to walk the terrain. Get your hands dirty. Build something yourself. Ask the engineer doing the work how they actually do it.Test your assumptions with first-hand experience. That’s how you develop real product sense. That’s how you see opportunities others miss by trusting frameworks that describe a world that doesn’t exist.The map is where you start. The terrain is where you build.Listen on Apple Podcasts ↗ or Spotify ↗Guest: Matthias Wagner* LinkedIn: Matthias Wagner ↗* Company: Flux.ai ↗ Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

Most teams aren’t doing the work to make a product launch successful. They’re pontificating in conference rooms. Debating specs. Trying to intellectually arrive at the right answer.The work looks different. The work looks different. Like Steve Jobs said, “There’s just a tremendous amount of craftsmanship in between a great idea and a great product… Designing a product is keeping 5,000 things in your brain and fitting them all together in new and different ways… And it’s that process that is the magic.”It looks like Dan De Mars and his team at Current Backyard are cooking 500 pizzas in two weeks. Prototyping. Testing with real data. Seeing if they can actually deliver before promising anything to the public.Crust thickness. Topping load. Heat curves. App guidance. Mouthfeel. Every variable they could isolate became another run, another data point, another step toward something that felt right—not just something that looked good in a deck.This is what intentional design actually looks like.Dan, head of product at Current Backyard ↗, doesn’t believe in perfection out of the gate. He believes in creating the conditions where a team can learn fast, fail often, and use their collective taste to sort signal from noise.The result? An electric pizza oven that lets a first-timer cook restaurant-quality pizza without the friction, the learning curve, or the open flame.But the insight goes beyond pizza ovens.Great products feel inevitable from the outside because teams did unreasonable amounts of work on the inside. They ran tight feedback loops. They invited more eyes. They treated taste as a filter over hundreds of experiments, not a single flash of genius.Dan also talks about designing for “limited grillers”—urban dwellers constrained by space, fire restrictions, or time—who still want great food without the heroics. It’s a masterclass in finding underserved segments and building for real constraints.If you’ve ever wondered how “it just works” products come together, this conversation is the blueprint.Listen on Apple Podcasts ↗ or Spotify ↗LinksDan De Mars on Linkedin ↗Current Backyard ↗00:00 The Essence of Design01:17 The Journey of a Designer02:17 Philosophy of Design03:25 Unlearning and Relearning09:44 Innovating Outdoor Cooking18:41 Targeting the Modern Cook25:56 Innovative Launches and Product Expansion26:52 Competing with Convenience: The Pizza Oven28:26 Designing for User Experience31:05 Prototyping and Iteration Process34:31 Balancing Functionality and Aesthetics44:29 Final Thoughts and Future Directions Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

Enterprises do not have an AI problem; they have an AI governance problem.In my recent conversation with David Trier, VP of product at ModelOp, he described the current state inside large organizations as “the Wild West of AI”—dozens of teams, hundreds of tools, and no shared way to get models safely into production.The reality is that many enterprises are staring at portfolios of 50 to 100 generative AI use cases, but only a handful ever make it into production, often taking six to 18 months to ship.What clicked for me in this episode was David’s analogy: ModelOp is essentially ServiceNow for AI.ServiceNow gave IT leaders a consistent, auditable way to turn messy tickets into reliable service management. ModelOp does the same for AI initiatives: it sits at the enterprise layer, orchestrating 10 to 12 teams and systems—data, security, legal, risk, compliance, infrastructure—so AI projects move through a repeatable playbook instead of one-off review cycles.David walked through a financial-services case where this approach cut time-to-production in half, turning 18‑month science projects into AI services that ship in weeks and generate business value before models degrade.For product leaders and CTOs, the takeaway is simple: if AI is a C‑suite–sized investment, it needs C‑suite–grade governance, not grassroots experimentation scattered across the org.If you are thinking about how to move from proof‑of‑concept chaos to an enterprise AI operating model, this episode is worth your time.Listen on Apple Podcasts ↗ or Spotify ↗Mentions* ModelOp ↗* David Trier ↗ Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

Show Notes:In the latest episode of the Way of Product Podcast, I had the pleasure of chatting with Brian Donohue, Vice President of Product at Intercom. Brian has been a critical player at Intercom for over 11 years, where he has navigated the company’s growth and transformation, especially in the ever-evolving world of AI integration.Brian shared his insights and experiences in transforming product development at Intercom, focusing on building a Fin AI agent that’s set to redefine customer support.With over two years dedicated solely to AI, Brian discussed the company’s journey from its early machine learning beginnings to embracing large language models.Connect with Brian on LinkedInListen to The Way of Product: Apple Podcasts or SpotifyActionable Takeaways✅ Embrace the uncertainty and potential of AI-driven product innovation.✅ Aligning incentives through outcome-based pricing instead of traditional SaaS models.✅ Balancing traditional product management structures with innovative AI development approaches.Time Stamps04:15 AI Integration in Product Development07:40 Architectural and Product Thinking in AI11:05 Challenges and Innovations in AI Implementation18:00 Continuous Improvement and Reassessment24:50 Inherited Product Design Flaws31:35 Technical Rigor and Product Validation37:10 Evolving Product Management Practices42:15 The Role of AI in Modern Product Development49:20 Outcome-Based Pricing Explained55:00 AI Transformation and R&D Services59:30 Adapting Product Development to Customer Needs66:45 Final Thoughts and Future Outlook70:20 Connecting with Brian Donahue Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

“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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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 Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe