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. 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

  2. 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/⁠

  3. 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/⁠

  4. 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/⁠

  5. 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/⁠

  6. Jun 3

    60: The Future of AI Starts With Real-World Data (with Nico Posner)

    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 Nico Posner, VP of Product Management at Q3D Sensing and a veteran product leader whose career spans some of the world’s most innovative companies, including LinkedIn, eBay, Clover, and Xero. Nico has spent years leading technology and AI-driven product innovation across industries, helping scale products from early-stage concepts to global adoption. At Q3D Sensing, he’s now focused on the next frontier of AI: capturing and digitizing the real world through advanced LiDAR and spatial sensing technology. With deep experience in AI, predictive analytics, product strategy, and emerging technology, Nico brings a unique perspective on how real-world data is becoming the foundation for the next generation of AI systems, robotics, construction tech, digital twins, and spatial computing. THE SUMMARY What happens when AI moves beyond text and begins interacting with the physical world? Nico Posner breaks down why the future of AI depends on accurate, real-world spatial data — and how LiDAR technology is unlocking entirely new possibilities across industries. The conversation explores the launch of Q3D Sensing’s new OraGo 3D reality capture LiDAR sensor and why accessible, affordable spatial sensing could become a foundational layer for AI-powered workflows. Nico explains how modern LiDAR systems work, why current enterprise solutions are often too expensive or impractical, and how new tools are democratizing access to high-quality 3D data capture. Polly and Nico also dive into: • The growing role of real-world data in AI systems • How LiDAR enables digital twins, robotics, construction intelligence, and spatial computing • The difference between consumer-grade scanning and professional LiDAR systems • Why edge processing and on-device rendering matter for enterprise workflows • How AI is accelerating innovation, product strategy, research, and operations • The future of AI-powered infrastructure, warehouses, and physical environments • Lessons from building products at both startups and global technology companies • The importance of solving real customer pain points when developing AI products This is a fascinating look at the intersection of AI, hardware, spatial computing, and product innovation — and why the next wave of AI breakthroughs may depend less on prompts and more on understanding the physical world around us. 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 Nico Posner LinkedIn: https://www.linkedin.com/in/nicoposner/ Q3D Sensing Website: https://www.q3dsensing.com/ Q3D Sensing LinkedIn: https://www.linkedin.com/company/q3d-sensing/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠  AI Career Boost: ⁠https://www.aicareerboost.com/⁠

  7. May 11

    59: Why Most Companies Are Using AI Completely Wrong (with Bill Takacs)

    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 Bill Takacs is a veteran product executive with over two decades of experience building and scaling platforms across SaaS, security, analytics, AI, and enterprise infrastructure. He’s currently VP of Product at MTrain, where he leads product and engineering—growing the business past $10M+ ARR, cutting platform costs by 50%, and doubling team velocity. A proven zero-to-one operator and turnaround leader, Bill’s background includes roles at Salesforce, AOL Instant Messenger, O’Reilly Media, HP, and multiple venture-backed companies. He’s also a former U.S. Army Ranger and Captain, bringing a unique blend of disciplined execution and bold innovation. In this episode, we’ll dive into operationalizing AI in enterprise products, scaling efficiently, and leading high-impact product teams. THE SUMMARY If you’re not adopting AI, you’re already behind: This isn’t incremental tech — it’s a step-change. Companies that treat AI as a “nice-to-have” efficiency tool will lose to AI-native competitors with lower costs, faster execution, and fundamentally different products. Survival depends on embracing it now. Most companies are using AI wrong and too safely: Simply making existing processes faster is the least imaginative use of AI. The real opportunity is redesigning workflows and products entirely — not just layering AI on top of old systems. Start with workflows, not hype: The smartest entry point isn’t “build something cool with AI” — it’s identifying repetitive, structured tasks and automating them. Map the process step-by-step, then apply AI where it actually removes friction. Agents are coming faster than most people think: We’re moving toward a world where teams manage AI agents that do the work — writing code, running workflows, even transacting. The shift from “tools” to “autonomous workers” is already underway. Roles are collapsing — not just evolving: AI is blurring boundaries between product, design, and engineering. Tasks that once required multiple roles can now be done by one person with AI support. This will fundamentally reshape team structures. No one actually knows the playbook yet: There is no “best practice” right now. Waiting for clarity is a losing strategy — the only way forward is experimentation, failure, and iteration. AI-first companies will outpace incumbents: Startups built natively with AI will have massive advantages: smaller teams, faster builds, and radically lower costs. Incumbents must actively disrupt themselves or risk irrelevance. The simplest advice: just start: Don’t overthink it. Pick a painful, repetitive task, try to automate it, and learn by doing. Momentum beats strategy at this stage. 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 Bill Takacs LinkedIn: https://www.linkedin.com/in/btakacs/ My links LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠  AI Career Boost: ⁠https://www.aicareerboost.com/⁠

  8. Apr 27

    58: The Hidden Problem With AI That No One in Tech Wants to Talk About (with Shampa Banerjee)

    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 Shampa Banerjee, PhD, is a powerhouse product leader who has scaled global digital platforms from scrappy startups into billion-dollar growth engines. As EVP and Chief Product Officer of Pluto TV at Paramount, she helped drive the platform from 20 million to over 50 million monthly active users while accelerating revenue to $1 billion ahead of schedule, expanding the service across Latin America and Europe. Prior to that, Shampa led the growth of Eros Now to 150 million users across 135 countries, delivering an extraordinary 240% year-over-year subscription growth. Over the course of her career, she’s served as both CPO and CTO across venture-backed startups and Fortune 500 companies, building world-class product, engineering, and data teams from the ground up. Trained as a physicist, Shampa brings a rare ability to recognize patterns in complex systems—pairing bold product vision with disciplined experimentation. Today, she advises growth-stage startups and global enterprises on scaling impact through AI, product strategy, and global go-to-market leadership. And in this episode, we’re diving into what it takes to scale digital platforms globally, the leadership behind building billion-dollar product ecosystems, and how AI and data are shaping the future of product strategy. THE SUMMARY AI adoption is failing in many companies — and nobody wants to talk about it: Many organisations are blindly adding AI because leadership mandates it, not because it solves a real problem. The smarter approach is to first ask whether AI is even the right solution. If it doesn’t improve growth, retention, or economics, it’s just expensive hype layered on top of existing systems. Understanding how AI works matters more than just using it: Treating AI like a magical tool leads to frustration when it produces imperfect results. Modern AI systems are probabilistic by nature — meaning uncertainty is built into how they work. Leaders who understand this design guardrails, human-in-the-loop processes, and better prompts instead of dismissing the technology as “wrong.” AI should drive growth — not just cost cutting: Too many companies frame AI purely as a way to reduce headcount or operational costs. The real opportunity is using it to expand capabilities, unlock new products, and scale output. Businesses that only focus on savings risk shrinking themselves instead of multiplying their impact. The AI transformation requires three shifts: People, Product, and Process: The biggest challenge isn’t the technology — it’s organisational change. Teams must get comfortable with uncertainty, rethink what products they should build, and redesign processes that were inherited from the manufacturing era. Companies that only upgrade tools without updating culture and workflows will stall. The AI revolution mirrors the early internet — but at a much faster speed: Just like the dot-com era, many experiments will fail, but the underlying ideas will eventually reshape industries. Concepts like Webvan looked wrong in the early 2000s, yet later became the foundation for companies like Instacart. Today’s AI experiments may look messy, but they are laying the groundwork for tomorrow’s dominant platforms. Technical credibility still matters for leaders: Leaders who understand the mechanics behind technology gain trust with engineering teams and make better strategic decisions. Getting hands-on — even building a small prototype — helps leaders translate between executives and technical teams and prevents unrealistic expectations about what technology can actually do. Hands-on experimentation is the fastest way to understand AI

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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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