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. 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/⁠

  2. 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/⁠

  3. 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

  4. 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

  5. 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/⁠

  6. Jul 13

    Ep 63: The AI Skills That Will Matter Most Over the Next 5 Years (with Anne Cantera)

    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 Cantera is the founder of Elementyl Intelligence, where she helps organizations turn AI from a buzzword into practical, production-ready products and systems. With expertise spanning conversational AI, voice AI, enterprise AI agents, conversation design, and AI product strategy, she has led large-scale AI initiatives across industries including legal technology, telecommunications, and healthcare. She is also the creator of Voice of AI, a free learning platform that helps designers, product managers, developers, and other professionals build practical AI skills for today's rapidly changing job market; and an active member of the Agentics Foundation community. Drawing on both technical and business experience, Anne brings a pragmatic perspective on what it really takes to build AI products that people trust and use.  THE SUMMARY In this episode of AI Product Leader, Anne and Polly explore what separates successful AI initiatives from the many projects that struggle to deliver value. They discuss why simply adding generative AI to an existing product isn't a strategy, how user experience and conversation design play a critical role in AI adoption, and why organizations need to think beyond technology to build systems that work across voice, chat, human support, and other customer touchpoints. Anne also explains why enterprise AI projects often fail before they begin and how the right planning and expertise can save both time and money. The conversation also looks at the future of AI careers and product development. Anne shares why she launched Voice of AI to make AI education accessible, the practical skills she believes professionals should be learning today, and how AI is reshaping opportunities for designers, product managers, and developers alike. Finally, she offers her perspective on where AI is heading next. From adaptive user interfaces and personal AI assistants to the growing importance of trust, security, and building products that people genuinely want to use. Whether you're leading AI initiatives, building AI products, or preparing for the next stage of your career, this episode offers practical insights grounded in real-world experience. 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 Cantera LinkedIn: https://www.linkedin.com/in/anne-cantera/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

  7. Jun 29

    62: How an ALS Diagnosis Inspired an AI Companion (with Kirstin Maurer)

    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 Kirstin Maurer is a healthcare and AI product leader with more than 18 years of experience building enterprise software, digital health platforms, and AI-powered products. During her time at Truepill, she helped scale a $20M telehealth platform and introduced generative AI capabilities that reduced post-call documentation time by 75%. Today, she is the founder of ALS Care Companion, an AI platform designed to provide people living with ALS and their caregivers with trusted, accessible support 24/7. Drawing on both professional expertise and personal experience with ALS in her own family, Kirstin is building technology that addresses real-world healthcare challenges.  THE SUMMARY In this episode of AI Product Leader, Kirstin shares how her family's experience with ALS inspired her to create ALS Care Companion, an AI-powered care navigation platform built from more than 67 trusted medical and advocacy sources. She explains why generative AI makes it possible for individuals to tackle meaningful problems that may not have been commercially viable just a few years ago, and why healthcare remains full of opportunities for AI to improve patient and caregiver experiences. Kirstin also reflects on her own transition into AI, from casually using tools for research and brainstorming to diving deep into hands-on experimentation, taking courses, and launching a production system used by dozens of families. She discusses how building something tangible transformed her confidence, helped her secure her first director-level role, and gave her a compelling story to share in interviews. Throughout the conversation, Kirstin offers practical advice for product leaders looking to grow their AI skills: choose a problem you genuinely care about, start building before you feel ready, and learn through experimentation. Whether you're trying to break into AI, advance your career, or create products with meaningful impact, this episode provides a candid look at what it takes to turn curiosity into real-world experience. 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 Kirstin Maurer LinkedIn: https://www.linkedin.com/in/kirstin-hartos-maurer/ ALS Care Companion: https://www.linkedin.com/company/als-care-companion/ Empower Your Digital Journey: Cybersecurity Basics & AI Tools for the ALS Community: https://www.als.org/webinars/empower-your-digital-journey-cybersecurity-basics-ai-tools-als-community My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

  8. Jun 16

    Ep 61: The AI Skill Most Directors Still Don't Have (with Courtney Kingsbury)

    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 Courtney Kingsbury is the Director of AI Strategy and Data Governance at a renewable energy asset management company. With a background spanning analytics, enterprise operations, product strategy, and AI systems development, she transitioned into AI by building real-world applications, including an enterprise document intelligence platform and a conversational AI solution that helped automate a City of Phoenix grant program. Her experience offers a practical perspective on how professionals can successfully move into AI leadership roles. THE SUMMARY In this episode of AI Product Leader, Courtney shares how she intentionally pivoted into AI, the projects she built to develop hands-on experience, and the steps that helped her secure a Director-level AI role. She discusses the importance of creating a portfolio, learning to prototype with AI tools, and why leaders who can turn ideas into working demonstrations have a growing advantage. The conversation also explores AI-assisted development, building enterprise AI systems, working with legacy data, and the tools Courtney relies on today, including Claude and Claude Code. Whether you're a product leader, aspiring AI professional, or someone looking to build practical AI skills, this episode offers valuable lessons on learning by doing and standing out in an increasingly AI-driven workplace. If you've been wondering how to move from AI curiosity to real-world impact, this conversation provides a roadmap filled with actionable insights, candid lessons, and inspiration from someone who successfully made the leap. 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 Courtney Kingsbury LinkedIn: https://www.linkedin.com/in/courtney-kingsbury/ 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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