Episode 127: Answering Questions About Digital Transformations

Dheerja Kaur, Vice President of Product Management at Robinhood, joins Melissa Perri on the Product Thinking Podcast to discuss her journey from engineering to product leadership. Her experience integrating design and user experience into product development at Robinhood has fostered a culture of ambitious thinking and learning by doing.Dheerja shares insights into balancing experimentation with strategic objectives and emphasizes the importance of empowering product teams to think big while aligning with organizational vision. Would you like to empower your product teams to think ambitiously while staying aligned with business goals? Don't miss out on Dheerja's insights.You’ll hear us talk about:07:34 - Defining the Product Manager RoleDheerja reflects on her transition from software engineering to product management at ESPN and how she navigated the shift from a technical role to a strategic one.13:01 - Coaching without MicromanagingDheerja shares strategies on finding the balance between providing guidance to new PMs and allowing them the autonomy to grow, fostering a supportive learning environment.28:09 - Balancing Experimentation with Ambitious GoalsDheerja discusses how to encourage teams to think big and have a portfolio of bets to achieve ambitious objectives while maintaining a culture of learning and experimentation.Episode resources:Dheerja on LinkedIn: https://www.linkedin.com/in/dheerja/Robinhood website: https://robinhood.com/Check our new course: https://productinstitute.com/p/mastering-product-strategy-overviewTimestamps:00:00 Coming Up00:56 Intro06:29 Dheerja’s journey into product13:01 Coaching PMs without micromanaging17:53 Learning Design22:16 UX In Finance28:09 Balancing experimentation with ambitious goals33:32 Proving the business value of great design38:43 Embracing risk

In this episode of the Product Thinking Podcast, we are joined by Kristin Dorsett, COO at Viator.We dive into how Kristin and her team are building a culture of experimentation, and what it takes to move fast without losing alignment.Viator, under the TripAdvisor umbrella, has embraced a learning mindset that blends data, customer feedback, and rapid iteration. Kristin shares how cross-functional collaboration empowers decision-making and why they’ve built systems that encourage teams to learn from both successes and failures.If you're aiming to understand how to balance experimentation with measurable success in your organization, this episode is a must-listen!You’ll hear us talk about:15:14 Embracing Failure to SucceedKristin discusses the importance of cultivating a mindset that celebrates learning from failures and iterating quickly to achieve collective success.28:29 The Role of AI in Product StrategiesHow Viator uses AI to improve customer experiences by focusing on solving practical problems, avoiding the trap of using technology for technology’s sake.22:50 Leveraging Customer FeedbackKristin explains how Viator's voice-of-the-customer program helps product managers identify key areas of improvement, leading to significant enhancements in their checkout conversion.Episode resources:Kristin on LinkedIn: https://www.linkedin.com/in/kristindorsett/Viator website: https://www.viator.com/Try Liveblocks: https://liveblocks.io/Timestamps:00:00 Introduction03:12 Dear Melissa06:18 Transition to COO12:34 Culture of experimentation17:48 Practical AI strategy22:34 Voice of the customer31:28 Cross-functional leadership

Join Melissa Perri on the latest episode of the Product Thinking Podcast as she chats with Jake Knapp, creator of Design Sprint at Google, and general partner at Character Capital. Known for for his seminal book “Sprint”, Jake discusses nuances from his latest book, "Click," and emphasizes the critical role differentiation plays in product success.This episode dives into the importance of starting product ideation with a clear differentiation strategy, ensuring that by the time you're ready to launch, you're not just another face in the crowd. Learn how to apply Jake's insights to make your products stand out from the rest, using the Foundation Sprint.Want to understand how to make your product unique in today's competitive market? Tune in for some practical takeaways from Jake's extensive experience helping startups and established companies refine their product strategies.You'll hear us talk about:5:53 - The Power of DifferentiationJake explains why thinking about differentiation should be the starting point of any product project, and how it connects to finding product-market fit.16:48 - Foundation Sprint to Design SprintJake walks through how a two-day foundation sprint can set the perfect stage for design sprints, helping teams define their hypotheses and move quickly from ideas to testable prototypes.35:53 - Lean Startup vs. Design SprintExplore the similarities and differences between Lean Startup and Design Sprint methodologies, and why rapid iteration and experimentation are key to product success.Episode resources:Click book: https://www.theclickbook.com/Jake on LinkedIn: https://www.linkedin.com/in/jake-knapp/Try Liveblocks: https://liveblocks.io/Timestamps:00:00 Introduction02:57 Dear Melissa06:57 Finding the gap before building14:39 Foundation sprint and why differentiation matters25:21 Customer research timing and magic lenses30:29 How to use lenses for decision-making35:53 Lean Startup vs design sprint and planning time43:19 Reclaim case study

Rebecca Shaddix, a seasoned marketing executive and go-to-market strategist, joins Melissa Perri to explore the balance of acceptable mistakes in market strategy. Rebecca discusses the importance of defining acceptable mistakes to avoid unnecessary delays and to better align team efforts with strategic goals. This episode focuses on how acknowledging acceptable mistakes can accelerate development without compromising core objectives.Rebecca also addresses the overemphasis on latest trends like AI, stressing the importance of intentional use rather than succumbing to hype. She provides insights into managing internal pressures and steering conversations back to meaningful customer outcomes.If you want to learn how to effectively balance strategic goals with market pressures while maintaining a focus on customer value, tune in to gain practical insights from Rebecca’s experiences.You’ll hear us talk about:09:04 - The Concept of Acceptable MistakesRebecca explains what an acceptable mistake entails, offering examples such as opting for fewer customer interviews to accelerate go-to-market strategies without significant risk.29:19 - Navigating AI HypeDiscusses the cycle of trendy technologies and how AI has become a prevalent, though often superficial, part of product strategy, emphasizing the importance of intentionality.15:32 - Product and Product Marketing PartnershipHighlights the need for a bidirectional relationship between product management and product marketing, focusing on how they should collaboratively drive strategy and insights.Listen to the full episode for more in-depth discussions and insights.Episode resources:Rebecca on LinkedIn: https://www.linkedin.com/in/rebeccashaddix/Try Liveblocks: https://liveblocks.io/Timestamps:00:00 Intro02:57 Dear Melissa06:17 Defining acceptable mistakes in go-to-market12:22 How product and go-to-market should collaborate17:48 What data product and marketing teams should track22:53 Turning competitive noise into strategy29:21 Responding to AI pressure from the market34:29 Crafting real differentiators, not buzzwords39:29 Advice for future product marketers

Oliver Seil, Vice President of Design at Belkin, joins Melissa Perri on the Product Thinking Podcast to explore how Belkin has transitioned into a design-focused company. Oliver discusses the role of design in creating products that resonate with users while fulfilling their functional needs. He shares how Belkin's design philosophy prioritizes consumer insights and prototyping to create products that are both innovative and intuitive.Through this episode, Oliver outlines the importance of integrating empathy and creativity in the design process and how these elements can foster a dynamic and inclusive company culture. He provides valuable insights into how product managers and designers can collaborate effectively, ensuring that the products not only meet market demands but also enhance user experiences.Interested in learning more about how design can drive product innovation and company culture? Tune in to gain practical insights from Oliver’s experiences at Belkin.You’ll hear us talk about:14:20 - The Importance of Executive Buy-In for Cultural ChangeOliver explains how having the support from top leadership, such as the CEO and a chief design officer, was crucial to fostering a design-focused culture at Belkin, promoting an environment where design is celebrated and integrated into the company's DNA.21:47 - Embracing Experimentation in DesignOliver shares strategies for balancing the need for rapid prototyping with the constraints of manufacturing timelines. He emphasizes the importance of testing and validating products through consumer feedback before full-scale production.25:29 - Collaboration Between Product Managers and DesignersHighlighting the significance of prototyping and communication, Oliver discusses how designers can effectively share their ideas and collaborate with product managers to bring innovative products to life.Episode resources:Oliver on LinkedIn: https://www.linkedin.com/in/oliver-seil/Belkin website: https://www.belkin.com/Try Liveblocks: https://liveblocks.io/Timestamps:00:00 Coming Up01:23 Intro06:00 Discovering design and joining Belkin10:30 Transforming culture through design19:20 User insights and product joy24:47 Pitching and selling design ideas30:35 Foster creativity and passion40:48 Building diverse teams

Join us for an insightful episode of the Product Thinking Podcast as we delve into the world of product operations with Jessica Soroky, the Senior Director of Product Operations at Pendo. In this episode, Jessica reveals the transformative strategies that have redefined Pendo's product operations, highlighting their innovative approach to integrating data and AI for enhanced product management.Jessica and I discuss the evolving landscape of product operations and the strategic shifts necessary to elevate the role beyond administrative tasks. We explore how Pendo empowers product managers by streamlining data insights and fostering a cross-functional communication framework that improves product launches and customer satisfaction.If you're eager to understand how product operations can drive strategic value and innovation within your organization, this episode is a must-listen. Gain practical insights and inspiration from Pendo's journey in optimizing their product operations.You’ll hear us talk about:09:17 - Evolution from Scrum Master to Program ManagerJessica explains the bold transition of Scrum Masters to Program Managers at Pendo, expanding their roles to oversee the entire product lifecycle and enhancing cross-functional collaboration.15:04 - Leveraging AI in Product OperationsDiscover how Pendo is integrating AI into their operations to reduce the burden of data tasks for product managers, allowing them to focus on strategic decision-making.20:56 - Implementing Effective Launch ProcessesLearn about the introduction of go-to-market checklists and launch briefs at Pendo, which have streamlined product launches and improved cross-departmental alignment.Episode resources:- Jessica on LinkedIn: https://www.linkedin.com/in/jessicasoroky/- Pendo: https://www.pendo.io/- Try Liveblocks: https://liveblocks.io/Timestamps:00:00 Coming Up01:17 Intro05:53 Jessica's journey to Product Ops leader11:48 Improving launches through whole-company alignment19:19 Structuring product ops for impact25:00 Building effective cadences and data rituals30:14 Driving data culture and exploring AI tools36:30 Making product ops strategic

Join Melissa Perri in an insightful episode of the Product Thinking Podcast featuring Hugo Froes, Head of Operations at OLX. In this episode, Hugo shares his remarkable journey from UX and service design to leading product operations, a transition that highlights the importance of bridging design with business needs.This conversation dives into how Hugo has effectively shaped product operations at OLX, focusing on process optimization, reducing friction, and empowering teams to deliver true value. Hugo’s approach showcases how strategic product operations can drive innovation and efficiency within organizations.Ready to explore how product operations can transform your organization? Listen to the full episode and gain practical insights from Hugo's experiences!You’ll hear us talk about:00:25:08 - Making OKRs Work Across the OrganizationHugo discusses the challenges and solutions for standardizing OKR frameworks to ensure consistent and measurable outcomes while allowing flexibility for team-specific practices.00:30:41 - The Product Ops MixHugo explains the multi-faceted approach of OLX's product operations team, focusing on improving efficiency, streamlining processes, and supporting organizational growth through strategic tooling.00:39:03 - Measuring Value in Product ManagementHugo and Melissa explore the importance of continuously validating product value against business outcomes, emphasizing learning over feature delivery.Episode resources:Hugo on LinkedIn: https://www.linkedin.com/in/hugofroes/Thoughts Unravelled: https://thoughtsunravelled.substack.com/Try Liveblocks: https://liveblocks.io/Timestamps:00:00 Coming Up01:01 Intro05:37 From UX to Product Ops: Hugo’s Journey09:17 Shift to Product Thinking16:33 Starting Product Ops at OLX21:23 Rethinking OKRs for Real Teams25:08 Making OKRs Work Across the Org30:41 The Product Ops Mix35:48 The Real Limits of AI43:07 What’s Next for Product Ops

In this episode, Eilon Reshef, co-founder and Chief Product Officer of Gong, joins Melissa Perri to discuss the transformative power of AI-driven technology in sales and product management.As Gong revolutionizes the sales industry, Eilon shares insights into building tools that empower salespeople and help them succeed. He dives into the challenges of scaling Gong to $100 million in ARR and the crucial role of focusing on end-user value.Eilon delves into how Gong captures and analyzes sales conversations to help teams close deals faster and increase revenue. He also reveals the unique organizational structure at Gong and the importance of design partners in their product development process.Want to discover how to harness AI to improve your sales processes and drive significant growth? Tune in to gain actionable insights from Eilon’s experience at Gong.You’ll hear us talk about:10:31 - Prioritizing Seller-Centric ValueEilon discusses the importance of emphasizing value for the end user, the salespeople, rather than just delivering organizational value. This approach has been critical to Gong’s success, helping build a product that sales teams love and rely on.13:50 - Implementing a Customer-Centric StructureLearn about Gong's unique pod structure, where product managers work closely with numerous design partners to receive continuous feedback and refine the product. This approach ensures that customer needs are always at the forefront.26:54 - Embracing AI in Product ManagementEilon provides advice for product managers on how to integrate AI into their work. He emphasizes the need to practice and understand AI capabilities to effectively incorporate them into product offerings.Episode resources:Eilon on LinkedIn: https://www.linkedin.com/in/eilonreshef/More about Gong: https://www.gong.io/Work at Gong: https://www.gong.io/careers/Liveblocks: https://liveblocks.io/Timestamps:00:00 Coming Up00:47 Intro02:51 Dear Melissa06:34 Eilon’s Intro & Gong's Founding Story10:31 Empowering Sales & Key Lessons22:08 Vision for AI & Its Impact on Sales31:41 Working with Design Partners & Beta Testing42:03 Reflections on Product Leadership

In this episode of the Product Thinking Podcast, Melissa Perri sits down with David Myszewski, VP of Product at Wealthfront. David shares his transition from working on the groundbreaking iPhone at Apple to leading product innovation in the fintech space. He dives into how Wealthfront's approach to fintech has been shaped by lessons learned at Apple, particularly the power of small, talented teams and high standards.David discusses Wealthfront’s strategy of integrating consumer research and customer support into product development, emphasizing the importance of understanding customer needs through both qualitative and quantitative data. He also highlights the significance of building a technology infrastructure that supports innovative financial products and services tailored to evolving market needs.Tune in to explore how Wealthfront is redefining fintech with a focus on reducing client costs, enhancing tax efficiency, and fostering better financial behaviors through technology-driven solutions. Want to learn how to leverage tech for financial innovation? Listen to the full conversation with David Myszewski.You'll hear us talk about:10:33 - The Role of Consumer Technology Experience in FintechDavid explains why consumer technology skills are more valuable than financial knowledge in fintech. He shares how Wealthfront prioritizes creating excellent user experiences over specific domain expertise.19:28 - Introducing New Financial ProductsDavid outlines Wealthfront’s strategy for evolving and introducing new products over time, focusing on reducing costs, saving taxes, and fostering behavioral change. He discusses the automation of processes to enhance client outcomes.29:06 - Prioritizing Innovation and Roadmap PlanningMelissa and David discuss the balance between strategic top-down priorities and bottom-up decision-making in setting the product roadmap. David describes how they align business and client needs to drive product innovation.Episode Resources:David on LinkedIn: https://www.linkedin.com/in/davidmyszewski/David on X: https://x.com/davewikipediaWealthfront: https://www.wealthfront.com/Timestamps:00:00 Coming Up00:56 Introduction02:48 Dear Melissa05:28 Career Journey from Apple to Wealthfront14:09 The Evolution of Wealthfront’s Mission19:28 Introducing New Financial Products29:06 Prioritizing Innovation and Roadmap Planning35:54 Finding Product-Market Fit at Wealthfront43:08 FinTech’s Future & Advice for Product Leaders

Join us for an insightful episode where we explore the digital transformation journey at Vanguard with Marco De Freitas, Chief Product Officer for Vanguard's Personal Investor Business, and Amber Brestowski, Chief Product Officer for the Retirement Business.Discover how Vanguard is modernizing client journeys, enhancing products, and building platforms that promise superior investment experiences. Marco and Amber share their strategies for leveraging AI and behavioral science to redefine client interactions, all while maintaining a strong focus on customer outcomes and innovation.Whether you're interested in digital transformation, product management, or financial services innovation, this episode is packed with practical insights that you won't want to miss. Want to learn how Vanguard is leading the charge in transforming financial services? Tune in for the full episode.You'll hear us talk about:10:32 - Aligning Strategy with Product ExecutionAmber discusses the importance of aligning product strategy with business goals at Vanguard. She emphasizes setting the right incentives and problems for product teams to solve, ensuring they focus on creating superior client experiences that drive competitive advantage.22:56 - Experimentation in Client ModernizationAmber shares how Vanguard uses a North Star approach with key OKRs to drive outcomes. She outlines strategies for engaging clients and improving retirement readiness through behavioral finance and agile experimentation.35:05 - Balancing Innovation and OptimizationMarco talks about Vanguard's approach to innovation, stressing the importance of client-centricity and empowering teams to innovate. He explains how a portfolio approach allows for both incremental improvements and moonshot projects, fostering a culture of continuous development.Episode Resources:Amber on LinkedIn: https://www.linkedin.com/in/amber-brestowski-019b56ab/Marco on LinkedIn: https://www.linkedin.com/in/marco-de-freitas-80416714/Vanguard website: https://investor.vanguard.com/Timestamps:00:00 Coming Up01:05 Intro09:10 Amber's Career Journey12:11 Marco’s career journey18:06 Modernizing Client Experience22:56 Experimentation in Client Modernization31:04 Aligning Business Strategy with Product Execution37:43 Behavioral Science in Digital Experiences46:50 Tackling Digital-First Transformation Challenges49:58 Closing reflections