The Way of Product with Caden Damiano

Caden Damiano

Every week I publish two conversations with people who build in technology and product. Each one comes with a narrative essay that puts you inside the conversation through my eyes. www.wayofproduct.com

  1. 3 days ago

    #194 Brian Donohue: Intercom threw their playbook out the window when AI got good — A case study on questioning your mental models.

    For years Brian Donohue thought the six-week cycle was the sweet spot — they’d arrived at it independently, the same place Basecamp landed. Then Intercom rebuilt its support product around large language models, and the cycle, the triad, and the stable teams all went out the window. Brian Donohue is the VP of Product at Intercom, where he leads product development for Fin, the company’s AI agent for customer support. Rising to prominence through more than a decade at Intercom, he became one of the defining figures behind the company’s transformation from a traditional SaaS helpdesk into an AI-first customer service platform. Under his leadership, Fin grew from a June 2023 launch with a 25% resolution rate to a sustained average of 65% resolution across all paying customers — widely regarded as one of the most measurable success records in enterprise AI product development. Previously, as Director of Product Management at Intercom, Donohue oversaw multiple product areas during the company’s rapid growth years, building deep expertise in outcomes-driven development, user onboarding, and messenger interface design. Before Intercom, he served as Director of Design at Houghton Mifflin Harcourt, where he accumulated more than twenty years of combined design and product leadership experience across enterprise and consumer contexts. Donohue has been a vocal advocate for technical rigor in AI product development, having championed the adoption of consumer-grade A/B testing methodologies within Intercom’s R&D organization and the firm’s transition to outcome-based pricing — charging per resolved customer conversation rather than per seat. Key Conversation Topics * Continuous reassessment as strategy — Intercom questioned “are we going bold enough?” every three months rather than making one big bet. Incremental big swings added up to a massive shift. * Inherited product blindness — Even though Fin was “built from scratch,” Intercom was still anchored to old UX decisions (button-based resolution confirmation) that took two years to recognize and fix. The fix actually significantly improved resolution rates. * Outcome-based pricing aligning incentives — Charging per resolution ($0.99/resolution) aligned what customers want, what the product team optimizes for, and what finance cares about in a way seat-based pricing never could. Resolution rate climbed from ~25% at launch to ~65%. * The AI operating model shift — Throwing out the six-week cycle, the triad, and traditional team topology. “Follow the work” rather than organizing around stable teams. Destabilizing but effective for speed. * Technical uplift required for AI product managers — Natural language as the programming interface doesn’t lower the bar — it raises it. Engineers think in rule sets and constraints; PMs now need that same rigor. * R&D Services as a critical new muscle — Forward-deployed R&D folks (like Palantir’s model) are essential for getting customers to value. AI transformation requires hands-on implementation support. PLG counterintuitively did NOT get amplified by AI. * Build to think / prototyping value for PMs — The real opportunity for PMs isn’t doing final design — it’s using AI tools to prototype fast enough to validate ideas before bringing in designers. Themes * AI agent product development at scale * Outcome-based pricing in SaaS * Organizational transformation under AI pressure * The paradox of technical uplift under “democratized” technology * A/B testing rigor borrowed from consumer product applied to AI Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newslettter I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

    49 min

  2. 5 days ago

    #193 Vance Morris: How Disney Parks Mastered Employee Engagement

    Vance Morris is the Founder of Deliver Service Now!, a consulting and coaching firm that teaches small and midsize businesses how to implement Disney-caliber customer experience systems combined with direct response marketing. Rising to prominence through a decade of leadership at Walt Disney World, he became the creative lead behind Chef Mickey’s — Disney’s flagship character dining experience at the Contemporary Resort — a concept whose systems have remained largely unchanged for more than 25 years. He also built and systematized three home service businesses in Maryland (a carpet cleaning company, a mold remediation company, and an Oriental rug washing facility) to operate on 90 minutes of his attention per week. Previously, as a manager and trainer at Walt Disney World through the 1990s expansion era, Morris served on the opening teams of the Yacht & Beach Club Resorts and Animal Kingdom, and acted as All-Island Duty Manager at Pleasure Island. He was recognized for generating $125,000 in business from a single marketing campaign, earning the Marketer of the Year award at a GKIC competition in 2015 and an International Marketing Award in a Dan Kennedy competition. His consulting client roster has included NASA, the Smithsonian, the Kennedy Center for the Performing Arts, Legal Seafoods, Tyson, Rainforest Café, and Compass Group. He has shared stages with Daymond John, Dan Kennedy, Joe Polish, and Jack Canfield across more than 40 years of speaking experience. Morris is also the creator of 52 Ways to WOW Your Customer, a free resource delivering one customer experience tactic per week of the year. Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

    52 min

  3. 25 Jun

    #192 Khurram Mir: If QA Is Blocking Your Launch, It Might Be Your Fault

    Khurram Mir is the Co-Founder and Chief Marketing Officer of Kualitatem, a specialized software quality engineering and information systems auditing firm operating across the United States, UAE, Saudi Arabia, Qatar, the United Kingdom, the Nordics, and Asia, and the Co-Founder of Kualitee, an AI-powered test management platform that grew out of Kualitatem’s internal tooling. Rising to prominence after beginning his career in software testing in 2001, Mir has spent more than two decades building the methodology and infrastructure that define enterprise QA at scale, accumulating over 500,000 hours of testing delivery and working with more than 200 client organizations across more than 350 applications. Mir co-founded Kualitatem in 2009 on the conviction that independent quality assurance should be a non-negotiable phase of every software development lifecycle, not an afterthought appended at the end of a release cycle. The firm achieved TMMi Level 5 certification — the highest maturity designation in the Testing Maturity Model integration framework — and has maintained ISO 27001 and ISO 9001 certification for six consecutive years. Kualitatem also developed an internal training institute to build consistent QA discipline across its geographically distributed team. A banking engagement that became a defining case study demonstrated that involving QA teams at the requirements stage — a shift-left approach — eliminated 33 percent of defects before formal testing even began. In 2016, Kualitatem productized the internal consistency tooling it had built to maintain uniform service quality across multiple countries, launching Kualitee as a standalone test management platform. The platform’s generative AI engine produces test cases directly from user stories and test scenarios, with Kualitatem’s own teams reporting a 23 to 27 percent reduction in testing time as a result. Kualitee now serves more than 2,000 engineering teams worldwide, including clients such as Emirates, T-Mobile, and Cox Enterprises, and has been recognized by G2 as a leading test management solution across multiple regional and segment reports. Mir serves as product manager for Kualitee in addition to his operational role at Kualitatem — a dual function that reflects the firm’s broader thesis: that the services mindset and the product mindset must be learned separately, even when one organization spawns the other. Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

    57 min

  4. 23 Jun

    #191 John Long: What Happens When Sales Stops Trusting Product

    John Long is the CEO and Co-Founder of Thynk AI, a Utah-based company building AI communication agents that handle the full pre-sales motion — cold outreach, lead qualification, scheduling, and beyond — without a human ever touching the conversation. Rising to prominence in enterprise technology sales over a 15-year career, Long built his reputation not as a manager of sales teams but as the kind of operator who embeds so deeply with product that the line between salesperson and builder disappears entirely. He was once the lone sales representative tasked with opening a brand-new market segment, and over the course of more than 100 trips with his product team, he helped construct what became a multimillion-dollar recurring revenue line from scratch. The product partner he worked alongside on that run is now his co-founder at Thynk AI. Founded in mid-2024, Thynk AI entered the market with a thesis that most AI SDR tools are window dressing — capable of sending a templated email but unable to hold a real conversation, respond to replies, or carry a prospect from cold contact through to a qualified meeting without human intervention. Long and his co-founder built Eric, Thynk AI’s AI sales agent, to close that gap end-to-end. Eric makes and receives calls, sends texts and emails, conducts live phone meetings, qualifies and disqualifies prospects, and books follow-ups autonomously. The company’s own website reflects the conviction: there is no human contact available until Eric has qualified you. In its first 90 days of operation, the platform generated $13,440,000 in pipeline for its users with no human SDRs and no ad spend. Long sees AI communication agents as a platform, not a point solution. Thynk AI has already extended Eric beyond outbound sales into customer service, HR, and accounting functions — any workflow where a business currently deploys a human to conduct a structured, repeatable conversation. The company operates from Lehi, Utah, and Long continues to serve as an advisor and speaker on practical AI deployment for growth-stage companies. Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

    43 min

  5. 18 Jun

    #190 Michael Ferranti: the $100 million lesson in what happens when product strategy overrides engineering discipline

    Michael Ferranti is the VP of Marketing at Unleash, the world’s largest open-source feature management platform, where he leads go-to-market strategy for a company that has more than 500 enterprise customers, 13,500+ GitHub stars, and 35 million downloads. Rising to prominence in the 2010s through a series of infrastructure and developer-tools companies, Ferranti built a reputation as a marketer who can translate technically dense products — container storage, zero-trust access, feature flags — into category-defining narratives for engineering and platform buyers. Previously, as Chief Marketing Officer at Teleport, the open-source infrastructure access platform, Ferranti joined in late 2021 and led the company’s marketing organization through a period of rapid enterprise expansion. Before Teleport, he spent nearly four years at Portworx as VP of Product Marketing and Corporate Marketing, where he helped build the category around Kubernetes-native persistent storage before Portworx was acquired by Pure Storage in 2020 in a deal valued at $370 million. Earlier in his career, Ferranti held marketing and product roles at ClusterHQ and at Rackspace, where he worked in the early days of OpenStack and most recently served as head of marketing for Mailgun by Rackspace, the developer email API. A Virginia Commonwealth University undergraduate, he relocated from Richmond, Virginia to the Paris metropolitan area in 2023. At Unleash, he has been part of the team that tripled ARR over three consecutive years, closed the $35 million Series B in March 2026 led by One Peak with participation from Spark Capital, Frontline Ventures, and Firstminute Capital, and expanded the customer roster to include Lloyds Banking Group, Wayfair, Prudential, and Lenovo. Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

    49 min

  6. 16 Jun

    #189 Issac Hicks: The Jobs AI Takes Are the Ones Nobody Wanted

    Issac Hicks is the Founder and CEO at Autonomi, an AI and automation consulting firm that helps mid-market and enterprise companies make critical work reliably repeatable. Rising to prominence in the applied AI space in the early 2020s, Hicks built Autonomi into a recognized force in business process automation — earning a seat on the Forbes Technology Council — by focusing on a thesis most consulting firms won’t touch: that the biggest source of wasted enterprise spend isn’t bad strategy, it’s the avalanche of tedious, repetitive operational work that consumes employees’ days. His firm has driven over $50 million in wasted spend back to the bottom line across deployments spanning custom applications, AI-enabled workflows, and end-to-end process automation. Hicks arrived at entrepreneurship through an unlikely path. He earned a Bachelor’s Degree in Aerospace, Aeronautical and Astronautical Engineering from Missouri University of Science and Technology (class of 2016), then spent roughly a year working as an aerospace engineer for the government before pivoting into Big Four business consulting. In that role he specialized in technology implementation for companies undergoing software migrations and acquisitions — work that put him inside some of the most operationally chaotic moments a company can experience. He watched acquired employees dread every transition, buried under work that existed solely because no one had built a system to handle it. In February 2021, he left consulting to found Autonomi with the conviction that the gap between a business problem and a scalable AI solution was bridgeable — and that bridging it was more valuable than any single consulting engagement. Autonomi operates across the full spectrum of automation maturity: from $5,000 pilot deployments to full-scale engagements starting at $25,000, with a primary focus on companies generating $2 million or more in annual revenue. The firm’s product portfolio includes Autonomy Books, an automated bookkeeping solution built specifically for CPA firms — a vertical where reconciliation and data entry remain stubbornly manual despite being near-perfectly suited to automation. Rather than pursue venture capital and the growth-at-any-cost model that comes with it, Hicks chose to build Autonomi as a profitable, self-sustaining business, retaining the operational control he now helps his clients achieve. Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

    51 min

  7. 11 Jun

    #188 Paul Glover: 33 Crimes, Five Years in Prison, and the Coaching Practice He Built From Nothing

    Paul Glover is the No BS Executive Workplace Coach at Paul Glover Coaching, where he works with C-suite leaders and high-performing executives across the United States on performance, accountability, and organizational resilience. Rising to prominence over more than two decades of coaching work following a complete professional reinvention, he became known for a performance coaching model built around blind spots, outcome-contingent fees, and a refusal to allow clients the comfort of self-deception. His largest active client is a billion-dollar distribution organization. Previously, Glover spent 30 years as a labor employment trial attorney in Chicago, earning a reputation as an aggressive courtroom litigator. His legal career ended in 1995 when he was indicted on 33 counts of white-collar crimes — including kickbacks, bribery, and tampering with government witnesses — and subsequently sentenced to federal prison. He refused to cooperate with prosecutors to reduce his sentence, and served approximately five years before beginning what would become a second career launched from scratch in his fifties. Released in 2001 with his law license revoked and ineligible for reinstatement for 13 years, Glover rebuilt entirely as a coach, eventually building a national practice. He structures his engagements as one-year contracts with 50 percent of his fee contingent on clients achieving mutually defined goals — a model designed to give him skin in the game and eliminate the incentive to let clients off the hook. His coaching approach draws directly from his own reckoning with ego, echo chambers, and the moment accountability finally broke through. Glover is the author of WorkQuake™, a book on surviving and thriving in the Knowledge Economy, praised by executive coach Marshall Goldsmith as agitating “the business status quo.” Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

    49 min

  8. 9 Jun

    #187 Joshua Altman: Story, Narrative, Brand: the three stages of communication—and why your narrative is probably the problem.

    Joshua Altman is the Founder and Managing Director of Beltway Media, a Washington, D.C.-based communications firm that provides fractional chief communications officer services to technology companies and startups. Rising to prominence over more than two decades in strategic communications, he became known for his Story-Narrative-Brand framework and Four Languages model, which help organizations align what people read, see, hear, and experience into a coherent communications strategy. His client roster spans scrappy startups to federal agencies including the U.S. Department of Justice and U.S. Department of Commerce. Previously, Joshua served as a multimedia journalist at The Hill, where he covered federal policy across energy, healthcare, immigration, defense, and criminal justice, and reported from the front lines of multiple high-stakes election cycles. His background as a news producer — shooting, editing, and cutting four to five videos per day — gave him the operational reps and editorial instinct that now underpin his consulting work. Joshua holds an M.A. in Communication, Culture and Technology from Georgetown University and a B.A. in Journalism and Mass Communications from The George Washington University. He is a member of The Telly Awards Judging Council and publishes The Comms Chief on Substack. Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

    49 min
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Every week I publish two conversations with people who build in technology and product. Each one comes with a narrative essay that puts you inside the conversation through my eyes. www.wayofproduct.com

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