Episode 263: From Product Leader to CEO

Creating great products at scale means widening your lens beyond roadmaps and features and learning how to run the business around the product. In this compilation episode, Melissa Perri pulls together three perspectives on what it takes for product leaders to operate at the next level: stepping into broader executive responsibility, building real ownership in teams, and making product decisions like disciplined investments.You’ll hear from Mercedes Chatfield Taylor on the most common paths to the CEO seat and what product leaders need to build that credibility, from board communication to revenue leadership and a more holistic operational view. Mercedes emphasizes succession planning and proactively taking on cross-functional responsibilities as the fastest way to expand scope and readiness.Sean Kim shares what true product empowerment looks like from environments like Amazon and TikTok, where PMs are given a metric to move and expected to negotiate resources, set plans, and own outcomes without being told what to build. Fabrice des Mazery closes by reframing product leadership as investment decision-making, focusing teams and stakeholders on risk, ROI, payback, and treating partners across the business as co-investors with skin in the game.You’ll hear us talk about:The product leader path to CEOMercedes Chatfield Taylor breaks down three common CEO trajectories and what tends to hold product leaders back. The conversation focuses on closing gaps like board-level communication, leading across revenue and finance, and proving you can operate beyond product by taking more off peers’ plates and building succession behind you.What empowerment actually means in practiceSean Kim describes a model where product teams are held accountable to clear business metrics and given autonomy to define the problem set, craft the plan, and execute. He explains how negotiation around headcount, timelines, and trade-offs becomes part of the job, and why learning from bets that do not work is expected rather than punished.Running product like an investment portfolioFabrice des Mazery argues that product leaders should translate work into investment language stakeholders already understand: risk, cost, margin, ROI, and payback. He connects time to money, pushes for proving causation, and outlines portfolio thinking that balances strategic investments, low-risk returns, micro-optimizations, and a small set of higher-uncertainty bets.Turning stakeholders into co-investorsInstead of debating features, Fabrice recommends surfacing risk transparently and asking stakeholders to commit resources and go-to-market support alongside product delivery. The goal is shared accountability, clearer trade-offs, and decision-making that feels like investing together rather than placing orders with a delivery team.Episode resources:Try Granola today: http://granola.ai/productinstituteCheck our courses: https://productinstitute.com/Episode 194: From Product Leader to CEO with Mercedes Chatfield-Taylor:https://www.produxlabs.com/product-thinking-blog/2024/10/23/episode-194-from-product-leader-to-ceo-with-mercedes-chatfield-taylorEpisode 193: Navigating Hyper-Growth with Sean Solme Kim (Former Head of Product at TikTok and Amazon Prime):https://www.produxlabs.com/product-thinking-blog/2024/10/16/episode-193-navigating-hyper-growth-with-sean-solme-kim-former-head-of-product-at-tiktok-and-amazon-primeEpisode 202: Transforming Product Teams into Investment Partners with Fabrice des Mazery:https://www.produxlabs.com/product-thinking-blog/2024/12/18/episode-202-transforming-product-teams-into-investment-partners-with-fabrice-des-mazeryMercedes Chatfield-Taylor on LinkedIn:https://www.linkedin.com/in/mchatfieldtaylor/Sean Solme Kim on LinkedIn:https://www.linkedin.com/in/seankim/Fabrice des Mazery on LinkedIn:https://www.linkedin.com/in/productroi/

Creating strong product organizations means aligning teams around outcomes, not outputs, and designing systems that enable learning at speed. In this episode, Melissa Perri brings together insights from multiple product leaders to explore what it takes to anchor on business outcomes, structure teams around value, and build the psychological safety required to learn through experimentation.You’ll hear from Jose Quesada, VP of Product Management for Mobile and Web at American Express, on why timing matters in transformation, how starting with outcomes changes decision making, and how experimentation only works when teams feel safe to fail. Melissa then expands on how organizing teams around value streams rather than architecture creates better incentives and clearer ownership as organizations scale.The episode also features Matthew Skelton, co-author of Team Topologies, who connects product thinking with team design, product operations, and enabling teams. Together, these perspectives highlight how structure, governance, and capability building must evolve together if product organizations want to move faster without sacrificing quality or trust.You’ll hear us talk about:Starting with outcomes instead of solutionsThe discussion explores why leading with vision and desired outcomes creates better alignment than jumping straight to features or roadmaps, and how focusing on what not to do is just as important as deciding what to build.Psychological safety and learning through experimentsJose Quesada explains why teams need permission to run experiments that fail, how mistakes build product intuition, and why softer skills matter more than perfect execution in uncertain environments.Organizing teams around value streamsMelissa Perri breaks down how value streams become the foundation for product team design, covering ownership, reporting lines, and why organizing around architecture often leads to busy work instead of customer impact.Enabling teams and product operations at scaleMatthew Skelton and Melissa discuss how enabling teams, product operations, and Team Topologies help large organizations manage cognitive load, place expertise effectively, and support long-term product strategy.Episode resources:Episode 230: Structuring Product Teams Around Outcomes with Jose Quesada: https://www.produxlabs.com/product-thinking-blog/episode-230-amex-product-outcomes-jose-quesadaEpisode 260: Avoiding Common Mistakes in Org Design: https://www.produxlabs.com/product-thinking-blog/episode-260-org-designEpisode 211: The Power of Team Topologies with Matthew Skelton: https://www.produxlabs.com/product-thinking-blog/episode-211-matthew-skelton-team-topologiesJose Quesada on LinkedIn: https://www.linkedin.com/in/josequesadamedina/Matthew Skelton on LinkedIn: https://www.linkedin.com/in/matthewskelton/Check our courses: https://productinstitute.com/

AI is moving quickly from experimentation into real products, but in regulated and high-trust environments the stakes are much higher. In this compilation episode of the Product Thinking Podcast, host Melissa Perri brings together perspectives from multiple product leaders to explore what it really takes to ship AI responsibly when accuracy, trust, and risk management matter.You will hear from Maryam Ashoori, who works at IBM and was involved in building Watsonx. She explains what AI agents actually are, why large language models hallucinate, and how guardrails and human oversight help teams manage calculated risk as systems become more autonomous.The episode also features Magda Armbruster, Head of Product at Natural Cycles, and Jessica Hall, Chief Product Officer at Just Eat Takeaway. Together they share how embedding regulation, prioritizing data privacy, and being honest about cost, governance, and capability building can turn compliance and trust into enablers rather than blockers for AI-driven products.You’ll hear us talk about:What AI agents can and cannot doMaryam breaks down how agents reason, plan, and take action, and why their probabilistic nature leads to hallucinations. She explains why this behavior is acceptable in low-risk contexts but dangerous in high-stakes domains without proper safeguards.Managing risk with guardrails and humans in the loopThe conversation explores how teams can design agentic guardrails and decision flows that keep AI systems close to verified truth, while escalating sensitive or high-risk situations to humans for review.Embedding regulation and privacy into product developmentMagda shares how Natural Cycles integrates quality assurance, regulatory, and compliance partners directly into day-to-day product work, and why strong privacy practices and user control are core product strategy rather than afterthoughts.The real cost of AI and long-term responsibilityJessica discusses the often underestimated costs of building and running AI systems, from unit economics to team capability, and why product leaders must balance simplicity, governance, bias mitigation, and customer trust instead of chasing hype.Episode resources:Check our courses: https://productinstitute.com/Maryam Ashoori LinkedIn: https://www.linkedin.com/in/mashoori/Magda Armbruster LinkedIn: https://www.linkedin.com/in/magda-armbruster-326692a/Jessica Hall LinkedIn: https://www.linkedin.com/in/jessica-hall-4223b0/Product Thinking Podcast Episode 241: https://www.produxlabs.com/product-thinking-blog/episode-241-ai-strategyProduct Thinking Podcast Episode 251: https://www.produxlabs.com/product-thinking-blog/episode-251-femtech-innovationProduct Thinking Podcast Episode 199: https://www.produxlabs.com/product-thinking-blog/2024/11/27/episode-199-the-true-cost-of-ai-beyond-the-hype-and-into-reality-with-jessica-hall

In this episode of the Product Thinking Podcast, Melissa Perri delves into the intricate world of organizational design for product management teams. She explores how to structure teams effectively around value streams, rather than falling into the trap of organizing by architecture.Melissa emphasizes the critical role of platform teams and the importance of starting with a solid product strategy before diving into organizational design.Melissa sheds light on the necessity for product managers to have a clear roadmap ownership and the challenges of maintaining short layers of control in large organizations to enable quick decision-making. She also discusses the benefits of platform teams in scaling services across an organization, stressing the need for high collaboration and alignment with customer-facing teams.Want to understand how to build a product management organization that maximizes business and customer value? Listen to this insightful episode for practical advice and strategic insights from Melissa Perri.You’ll hear us talk about:01:33 - Organizing Around Value StreamsMelissa discusses the importance of structuring product management teams around value streams, ensuring clear ownership of roadmaps and effective delivery of customer value.02:32 - Avoiding Organizational BottlenecksMelissa explains the drawbacks of having too many layers in decision-making processes within large organizations, advocating for shorter control layers to enhance efficiency and decision speed.06:38 - The Role of Platform TeamsThe episode highlights the strategic importance of platform teams in scaling services organization-wide, emphasizing the need for these teams to align closely with customer-facing value streams.Episode resources:Check our courses: https://productinstitute.com/

Srini Raghavan, Chief Product Officer at FreshWorks, joins Melissa Perri to discuss the evolving role of product management in the age of AI. He explores how product managers are transforming into "product builders" with AI as a catalyst for more integrated roles, collapsing traditional processes, and enabling rapid prototyping.Srini dives into the impact of AI on enhancing customer and employee experiences at FreshWorks. He shares insights on how AI agents are handling repetitive tasks, improving satisfaction, and delivering real outcomes through a relentless focus on customer needs.Curious about how AI is reshaping product management and the role of product managers? Tune in to hear Srini's insights on leveraging AI for creating uncomplicated user experiences and driving outcome-focused innovation.You’ll hear us talk about:05:15 - Transforming Product Managers into Product BuildersSrini discusses the shift towards product managers becoming more involved in design and prototyping phases, with AI reducing the need for separate UX and engineering inputs early on.18:45 - Enhancing Experiences with AI AgentsLearn about FreshWorks' approach to using AI agents to handle repetitive tasks and improve user satisfaction, providing a more human-like experience.28:30 - Delivering Uncomplicated User ExperiencesSrini explains the importance of simplicity in product setup and management, aiming to serve a diverse range of customers with straightforward user experiences.Episode resources:Srini on LinkedIn: https://www.linkedin.com/in/srinivasan28/Freshworks website: https://www.freshworks.com/Check our courses: https://productinstitute.com/

In this episode, Melissa Perri dives into the intricacies of product management with a focus on both inbound and outbound product management. Whether you're working on internal tools or customer-facing products, the strategic processes involved are crucial and similar across the board.Melissa discusses the importance of having a strategy, discovery, and delivery process in place to maximize the value stream and mitigate risks, regardless of the product's focus. Melissa provides examples of how internal tools, like algorithms for insurance claims or bank teller systems, can significantly impact customer experience. This episode emphasizes that the core principles of product management remain consistent, whether you're dealing with AI product management or traditional product strategies.Are you a product manager looking to enhance your understanding of both inbound and outbound product management? Tune in to this episode to gain valuable insights into effective product strategies and processes that can be applied to any product type.You’ll hear us talk about:1:37 - Understanding Inbound vs Outbound Product ManagementMelissa explores the differences and similarities between inbound and outbound product management. She emphasizes the necessity for a strategic approach in both areas, debunking the myth that inbound product management carries less risk.4:07 - Impact of Internal Tools on Customer ExperienceDiscussion on how internal tools like bank teller systems and insurance claim algorithms can significantly affect the customer experience. This section highlights the importance of strategic design for internal products.6:10 - Consistency in Product Management PracticesMelissa stresses that the fundamentals of product management, such as strategy and discovery, remain the same regardless of the product type. She highlights the importance of maintaining a focus on discovery and delivery in AI product management.Episode resources:Check our courses: https://productinstitute.com/

In this episode of the Product Thinking Podcast, Melissa Perri is joined by Michael Dodsworth, the founder and CEO of Fanfare. Michael shares his insights on the importance of storytelling in product management and how it can drive product success.He discusses his transition from engineering roles to leading innovative product launches that create immersive experiences and captivate audiences. Through his experiences, Michael emphasizes the significance of aligning strategic goals with customer engagement to elevate product performance.Tune in to explore how Michael's approach to storytelling and strategic alignment can transform your product launches into unforgettable experiences.You'll hear us talk about:07:36 - The Power of Storytelling in Product ManagementMichael Dodsworth explains the essential components of storytelling for product managers. He highlights the importance of simplifying stories to resonate with audiences and making them personal to leave a lasting impression.23:39 - Turning Product Launches into Immersive ExperiencesMelissa and Michael discuss how brands can create engaging and immersive experiences during product launches. Michael shares strategies to avoid negative aspects of product drops and ensure a memorable customer journey.29:28 - Applying Launch Lessons to Software ProductsMelissa asks Michael about translating product launch principles to software companies. Michael emphasizes the necessity of educating customers and having a clear narrative to drive the success of product launches in the tech industry. Episode Resources:Episode resources:Michael on LinkedIn: https://www.linkedin.com/in/michael-dodsworth/Fanfare: https://fanfare.io/Check the localization report: https://lokalise.com/library/data-reports/localization-revenue-report-2025/Check our courses: https://productinstitute.com/

In this episode, Melissa Perri discusses the common dilemma faced by product managers: whether to prioritize large, high-risk features or focus on delivering smaller, incremental updates. She delves into the considerations that should guide this decision, including the value to users, stakeholder goals, and the need for experimentation and risk management. Melissa shares insights on how to approach these decisions strategically to ensure both customer satisfaction and business success.Are you grappling with how to balance big projects against smaller, faster releases in your product strategy? Tune in to this episode to gain valuable insights from Melissa on making the right choices for your product and organization.You’ll hear us talk about:02:29 - The Value of Incremental ReleasesMelissa discusses the benefits of releasing smaller features incrementally, highlighting how they can provide immediate user value and inform future development decisions through feedback.04:13 - Managing Risk in Long-Term ProjectsHere, Melissa emphasizes the importance of de-risking multi-month projects with phased releases and feature flags, ensuring that stakeholders and users are aligned and informed throughout the process.05:01 - Balancing Stakeholder and User NeedsMelissa explores the tension between meeting stakeholder goals and delivering user value, offering strategies for product managers to align these often competing priorities effectively.Episode resources:Check the localization report: https://lokalise.com/library/data-reports/localization-revenue-report-2025/Check our courses: https://productinstitute.com/

Join us in this episode as Melissa Perri sits down with Vanessa Lee, VP of Product at Shopify, to explore the groundbreaking work being done in AI integration and agentic commerce. Vanessa sheds light on Shopify's AI assistant, Sidekick, which aims to revolutionize how merchants manage and grow their businesses.Discover how Shopify is pushing the boundaries of e-commerce with cutting-edge technology and a commitment to empowering entrepreneurs.Through engaging anecdotes and insights, Vanessa shares how Sidekick is not just a tool but a strategic partner for merchants, helping them navigate the complexities of entrepreneurship. We delve into the collaboration with OpenAI and how Shopify is leveraging AI to create seamless, innovative shopping experiences.Want to understand how AI can transform product management and e-commerce? Tune in to this episode for an enlightening conversation that explores the future of commerce and the evolving role of product managers.You’ll hear us talk about:05:19 - Shopify's Agentic AI AssistantVanessa explains how Sidekick, Shopify's AI assistant, was designed to be a co-pilot for merchants, proactively assisting with tasks like product creation and payment setup to help entrepreneurs succeed in their journey.36:38 - Partnership with OpenAIDiscover how Shopify partnered with OpenAI to integrate commerce functionalities into ChatGPT, making merchants' products discoverable and enabling direct checkouts within the AI platform.22:34 - Practical Advice for PMs Working with AIVanessa offers valuable advice for product managers looking to enhance their skills in generative AI and LLMs, emphasizing the importance of creativity and experimentation in developing innovative AI applications.Episode resources:Vanessa on LinkedIn: https://www.linkedin.com/in/vlaurenlee/Check the localization report: https://lokalise.com/library/data-reports/localization-revenue-report-2025/Check our courses: https://productinstitute.com/

Join Melissa Perri in this episode of the Product Thinking Podcast as she tackles the complex issue of managing an overwhelming workload as a product manager. A senior product manager shares their struggle of handling five engineering teams, a task typically assigned to multiple product managers. Melissa offers practical advice on how to communicate with leadership, prioritize effectively, and implement systems to manage scope.If you've ever faced the challenge of balancing broad strategic oversight with detailed management, this episode is a must-listen. Melissa's insights will help you understand how to align your team's work with company goals while maintaining quality and focus.You’ll hear us talk about:03:36 - The Classic Project Management Trade-OffMelissa discusses the well-known project management saying about scope, quality, and speed, explaining how product managers must often choose between these competing priorities.04:44 - Proposing Solutions to Manage WorkloadMelissa provides a framework for presenting options to leadership, including hiring additional product managers and weighing the opportunity costs of current workloads.07:40 - Building Internal Systems for Workload ManagementMelissa advises on creating internal systems to distribute work, allowing development leads to step into prioritization roles, thus enabling a more balanced workload distribution.Tune in to gain actionable strategies and ensure your product management approach aligns with your organization's strategic goals.Episode resources:Check the localization report: https://lokalise.com/library/data-reports/localization-revenue-report-2025/Check our courses: https://productinstitute.com/