The Way of Product with Caden Damiano

About my guest & how to find them online Karl Simon is the Co-Founder and CTO of Subatomic AI , an enterprise AI Co-Worker Agent platform that deploys customizable agents adapted to client workflows, philosophies, and reasoning patterns. Rising to prominence in the 2010s as a data and engineering leader across retail, healthcare, and life sciences, Simon became known for building globally distribu...

Listen to this episode on Spotify or Apple Podcasts “No one could ever take this over,” Jake says. “If he left or somebody else had to manage it, no one knows what’s going on here.” Jake Stauch tells me a story about a CFO and an expense report, and it changes the way I think about no-code tools. The CFO had a simple request for his IT team: when someone submits an expense report, get approval fro...

Radhika Dutt is the author of Radical Product Thinking , a product leadership movement and book that has been translated into multiple languages, including Chinese and Japanese. Rising to prominence in the 2010s and 2020s, she became known for codifying a vision-driven alternative to iteration-led product development used by teams across industries from fintech to government. She currently serves...

Saurabh Sharma is the Chief Product Officer at You.com , where he leads product, design, and research for AI agents that power critical business workflows across search and enterprise use cases. Rising to prominence in the 2010s through work at Google , he became known for scaling applied AI, search and discovery, and trust and safety systems to hundreds of millions of users globally. He is widely...

Anya Cheng is the Founder and CEO of Taelor , an AI-powered menswear rental and styling platform at the intersection of fashion, data, and artificial intelligence. Rising to prominence in the 2010s after leading product teams at Meta , eBay , Target , and McDonald’s , she became known for scaling digital products that touched hundreds of millions of users while bridging consumer behavior, growth,...

Maxine Anderson is the Co-founder and Chief Product Officer at Arist , where she helps build what is widely regarded as an emerging default enablement system for large enterprises. Rising to prominence in the early 2020s, she became known for transforming text-message learning experiments into an agentic enablement platform that operates directly inside Slack, Microsoft Teams, and SMS. Under her p...

Richard Yu is the Chief Product Officer at LucidLink , where he leads product strategy for the company’s cloud-native file system used by distributed creative and enterprise teams worldwide. Rising to prominence in the 2010s as an enterprise SaaS product leader, he became known for building mission-critical platforms that turn complex workflows into scalable, repeatable systems. He is widely regar...

Chris Silvestri is the Founder at Conversion Alchemy , where he helps B2B SaaS teams engineer message–market fit across web, sales, and email. Rising to prominence in the early 2020s, he became known for combining deep customer research, UX thinking, and decision-making psychology into scalable messaging systems that lift conversions rather than isolated campaigns. His work positions him as a wide...

Mustafa Kapadia is the Managing Director at Echo Point , where he helps product organizations use AI to eliminate operational drag and compound product velocity. Rising to prominence in the 2010s at the intersection of digital transformation and DevOps, he became known for translating emerging technologies into operating models executives could actually run. Today he is widely regarded as a leadin...

Matt D. Smith is the founder of Shift Nudge , a professional interface design training platform for working designers. Rising to prominence in the 2010s for his systematic approach to visual interfaces, he became known for turning over 20 years of interface design practice into a structured curriculum used by thousands of designers worldwide. His work on design patterns and tools has made him a wi...

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...

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 exitin...

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, compensa...

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 r...

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 und...

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, u...

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...

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 y...

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 gene...

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 pr...

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 ma...

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 som...

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 ha...

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, experimentat...

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 th...