AI Product Leader

Polly Allen

Weekly conversations with AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.

  1. 20h ago

    Why Is It So Hard to Prove AI Is Delivering ROI? (with Brian Stahlhammer)

    For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested  THE GUEST Brian Stahlhammer is an experienced product leader with a track record of building and scaling technology businesses. He helped transform FreeWave into an industrial IoT platform, scaled Calix's Smart Town to 10 million devices and $30 million in annual revenue in a year, and earned three patents at CableLabs. With a background in mechanical engineering, consulting, and business strategy, Brian brings a hands-on approach to AI product development, combining strategic thinking with practical experimentation. THE SUMMARY How can companies measure AI ROI, build useful AI products, and maintain human accountability as AI becomes part of everyday work? Brian shares his perspective on these challenges, drawing on his experience building AI-powered applications, including a wine recommendation tool, and developing AI solutions for business decision-making. He discusses why connected tools, shared organizational context, clear business outcomes, and effective AI governance matter when turning AI investments into measurable value. Brian also explains how product leaders can learn AI by building projects around their interests and improve results through adversarial prompting—asking AI to challenge assumptions, identify weaknesses, and critique its own outputs. His central message: AI should augment human judgment, not replace it. Learn how to get hands-on with AI, challenge its recommendations, and make better-informed product and business decisions. THE SHOW Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI. THE LINKS Have a question you want us to answer? Send it through to support@aicareerboost.com Brian Stahlhammer LinkedIn: https://www.linkedin.com/in/brian-stahlhammer/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

  2. Oct 20

    Stop Building AI Products Nobody Needs (with Anne T. Griffin)

    For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested  THE GUEST Anne T. Griffin is an AI product leader, fractional Head of Product Strategy, and consultant with 14 years of experience building products across Fortune 500 companies and AI-native startups. She has launched agentic AI products used by thousands of customers, helped drive over $1.8 million in customer expansion and renewal value through AI-powered workflows, and recently shipped 10 AI agents in under two and a half months. She also teaches AI courses for Pearson and O’Reilly and writes about AI strategy for Forbes. THE SUMMARY How do you build AI products that customers actually use and trust? Anne joins Polly Allen to share lessons from building multi-agent systems for cybersecurity, including how AI agents can simplify complex risk assessments, reduce manual work, and help non-technical users take action. She explains why successful AI products start with understanding customer needs—not adding AI for its own sake—and how to balance rapid experimentation with a minimum trustable product. The conversation also explores designing intuitive AI experiences that drive adoption, building reusable agent components, and how hands-on product leaders need to be with AI technology. Anne shares practical advice for evaluating AI tools, understanding the gap between prototypes and production-ready products, and developing the technical judgment needed to build reliable AI solutions that deliver real customer value. THE SHOW Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI. THE LINKS Have a question you want us to answer? Send it through to support@aicareerboost.com Anne T. Griffin LinkedIn: https://www.linkedin.com/in/annetgriffin/ https://griffinproduct.co/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

  3. Oct 5

    You Don’t Need to Know Everything About AI to Get Started (with Kavita Bond)

    For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested  THE GUEST Kavita Bondarenko is an agile delivery leader and Scrum Master with a decade of experience helping globally distributed teams deliver products across highly regulated industries, including space, telecommunications, and healthcare. Her background spans satellite platforms, healthcare modernization, stakeholder management, and cross-functional delivery. Now transitioning from project management into AI product management, Kavita brings both delivery expertise and growing hands-on experience with AI tools, including Lovable, Claude, AWS AI, and Azure AI. THE SUMMARY Kavita shares her transition into AI product management and explains how hands-on experimentation with AI tools has changed the way she thinks about products, users, and product development. She discusses using Claude and Lovable to iterate on PRDs, prototype features, and communicate UI changes through screenshots and visual edits. The conversation also covers how she approached learning AI from the ground up, the importance of understanding AI security and data in regulated industries, and her healthcare capstone project focused on improving patient eligibility and hospital admission workflows. Her practical advice for aspiring AI product leaders: don't wait until you know everything—choose one accessible AI tool, experiment with it, and learn by doing. THE SHOW Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI. THE LINKS Have a question you want us to answer? Send it through to support@aicareerboost.com Kavita Bondarenko LinkedIn: https://www.linkedin.com/in/kavita-bondarenko/ Email Address: kavita.dbond@gmail.com  My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

  4. Sep 21

    Why Your AI Product Needs a Plan Before You Write Code (with Amer Arab)

    For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested  THE GUEST Amer Arab is a product leader and solo founder who built ClearList.me, an AI-powered platform that turns photos into marketplace listings and simplifies the process of selling belongings. He developed the product using Claude Code, drawing on his background in computer science, UX, and product management. With experience at companies including Zynga and Peak Games, Amer has worked across localization, user experience, and product development. His earlier career included helping build an Arabic-language gaming experience that gained significant attention in the region. Today, Amer combines product strategy, AI-assisted development, and rapid experimentation to run his software business independently. His experience offers practical insights for product managers and aspiring founders interested in building AI products without relying on a traditional engineering team. THE SUMMARY How do you build a useful AI product without letting the AI make all the decisions? Amer explains why product managers should start with outcomes rather than simply asking AI to build an app. He shares his process for defining user needs, brainstorming solutions, mapping happy and worst-case paths, and building a minimum lovable product. Amer also breaks down his workflow for building with Claude Code, including multi-agent development, code reviews, security and scalability checks, and managing technical debt. He discusses how product managers can use AI to develop technical skills, why asking questions and reviewing AI-generated code matters, and how tools like Google Stitch and Claude skills support product development and marketing. THE SHOW Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI. THE LINKS Have a question you want us to answer? Send it through to support@aicareerboost.com Amer Arab LinkedIn: https://www.linkedin.com/in/amerarab/ ClearList: https://clearlist.me/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

  5. Sep 7

    The 5 Levels of AI Adoption Every Leader Should Understand (with Ale Ayestarán)

    For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested  THE GUEST Ale Ayestaran is a growth and operations executive with 15 years of experience building AI-powered systems and scaling businesses from early-stage startups to multi-billion-dollar marketplaces. A Stanford MBA and engineer, he has led revenue, operations, pricing, growth, and AI initiatives at companies including Shift, Mind, RelateIQ, and BCG. Today, Ale is Head of AI at Nexus Capital, where he works with portfolio companies on AI adoption and operating-model changes. His experience across technology and non-technology businesses gives him a practical perspective on how companies can move from AI experimentation to meaningful operational change. THE SUMMARY In this episode of AI Product Leader, Ale shares what he is seeing in AI adoption across mid-market companies, including the challenges created by legacy systems, data silos, limited technical resources, and difficult ERP migrations. He explains why companies may be able to add AI layers to existing systems in some workflows—but why AI isn't a magic replacement for strong infrastructure. Ale also breaks down a five-level model of AI adoption, from individual chat-based use to agentic team workflows and AI-native business models. He explains why leaders should get hands-on with AI, how to start by asking AI to perform real work, and how management roles may change as AI takes over more information-flow and operational tasks. THE SHOW Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI. THE LINKS Have a question you want us to answer? Send it through to support@aicareerboost.com Ale Ayestarán LinkedIn: https://www.linkedin.com/in/alejandroayestaran/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

  6. Aug 24

    What Happens When Everyone in Your Company Can Build With AI? (with Arun Biligiri)

    For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested  THE GUEST Arun Biligiri has more than two decades of experience turning emerging technology into business outcomes. He has founded startups and held leadership roles across product management, sales engineering, services, and development at companies including IBM and Hitachi, managing large P&Ls and driving significant new revenue. He is now the founder of Mitova.ai, an AI-native innovation platform focused on helping organizations manage and scale AI innovation. THE SUMMARY In this episode of AI Product Leader, Arun shares practical lessons on building successful AI products and managing innovation at scale. He explains why product-market fit and market timing matter more than the technology itself, and how AI is lowering the cost of prototyping while enabling people across an organization—not just engineers—to become builders. Arun also discusses how leaders can manage an influx of AI-generated ideas, the balance between being a strategic leader and getting hands-on, and his experience building a production AI product after decades away from programming. He explains how he uses AI for planning, cost modeling, design, testing, and iterative development—and why AI's greatest value may be helping teams make better product decisions before they build. THE SHOW Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI. THE LINKS Have a question you want us to answer? Send it through to support@aicareerboost.com Arun Biligiri LinkedIn: https://www.linkedin.com/in/biligiri/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠ August 26th Free Masterclass: https://www.aicareerboost.com/master-ai-leadership

  7. Aug 10

    What Working at an AI-First Company Really Looks Like (with Jeff Williams)

    For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested  THE GUEST Jeff Williams is a senior product leader with more than 25 years of experience in software and technology, including over a decade in product management. With a degree in computer science, he has led zero-to-one product launches, large-scale digital transformation programs, and enterprise platform initiatives across healthcare, SaaS, e-commerce, and patient engagement. His recent work has focused on healthcare technology, including interoperability, digital engagement, and products that support complex patient and provider workflows. He has held roles at Deloitte Digital, Loyal Healthcare, and WEX, and now works at OpenLoop, an AI-first healthcare company. Jeff brings a valuable perspective for product leaders because he made the shift into an AI-focused role after building practical AI experience himself. His story shows how experienced product professionals can develop hands-on AI skills, speak credibly about their work, and apply those skills inside a fast-moving company. THE SUMMARY In this episode, Jeff shares what it takes to move from traditional product management into an AI-first environment, including the skills, habits, and hands-on experience that helped him make the shift. He explains how OpenLoop uses tools such as Claude across product, engineering, sales, customer success, and operations to reduce manual work, improve communication, update product documentation, manage Jira workflows, and help teams move faster. The conversation also covers how Jeff built practical AI experience before landing the role, why product leaders need to become more hands-on, and how building a real AI project helped him speak credibly in interviews. Viewers will come away with concrete ideas for using AI in daily product work and preparing for leadership roles at AI-focused companies. THE SHOW Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI. THE LINKS Have a question you want us to answer? Send it through to support@aicareerboost.com Jeff Williams LinkedIn: https://www.linkedin.com/in/jeffawilliams/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠ August 12th Free Masterclass: https://www.aicareerboost.com/master-ai-leadership-2

  8. Jul 27

    Afraid You're Falling Behind in AI? Watch This First (with Viktoria Otstavnaya)

    For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested  THE GUEST Viktoria Otstavnaya is a Principal Product Manager specializing in modernizing complex systems and leading large-scale product transformations across telecom, fintech, healthcare, and utilities. Throughout her career, she's helped organizations dramatically reduce product launch times, accelerate customer onboarding, and deliver operational improvements through strong product leadership and cross-functional collaboration. With a background in software engineering and early experience applying AI to automate complex business processes, Viktoria brings a practical perspective on how product managers can successfully adopt AI, work effectively with AI vendors, and build confidence through hands-on experimentation. THE SUMMARY In this episode, Viktoria shares how her career evolved from Android development to product management, why understanding technology at a deeper level makes product leaders more effective, and how she began working with AI years before generative AI became mainstream. She discusses real-world lessons from integrating AI into enterprise products, including how product managers can get better results from third-party AI solutions by understanding vendor configurations, APIs, and implementation best practices. The conversation also explores the human side of AI adoption. Viktoria reflects on the fear many professionals feel about falling behind, explains how practical projects helped her build confidence, and offers advice for anyone looking to develop AI skills. Whether you're leading AI products today or preparing for your first AI initiative, this episode offers actionable guidance on learning, experimenting, and staying effective in a rapidly changing field. THE SHOW Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI. THE LINKS Have a question you want us to answer? Send it through to support@aicareerboost.com Viktoria Otstavnaya LinkedIn: https://www.linkedin.com/in/viktoria-otstavnaya/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

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Weekly conversations with AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.

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