Stacked Sessions

Jeff Keyes
  • 5.0 (1)
  • Business
  • Updated Biweekly

Stacked Sessions is the podcast where software engineering meets business strategy. Hosted by Allstacks, each bi-weekly episode brings together executives, engineering leaders, and industry experts to explore how product and engineering drive measurable business impact. From ROI and board-level reporting to the future of AI in software delivery, we go beyond productivity to focus on what matters most: turning engineering investments into strategic advantage. Whether you’re a CTO, a C-suite executive, an executive member, or an aspiring executive—Stacked Sessions delivers the insights you need to connect code to capital.

  1. The Task Framework That Makes AI Agents Your Product's Superpower With Matvey Bryskin

    Jun 30

    The Task Framework That Makes AI Agents Your Product's Superpower With Matvey Bryskin

    Most companies are overwhelmed by the rapid advancements in AI and product management—yet few know how to harness this power effectively. Matvey Bryksin, founder of Product Map and a seasoned product leader, reveals the groundbreaking framework that’s transforming how product teams operate in an AI-driven world. If you're tired of bottlenecks caused by outdated processes, this episode offers a fresh perspective: structured AI agents, a task-centric approach, and new ways to organize product knowledge that save time, reduce errors, and empower you to ship faster. Discover how AI can eliminate routine bottlenecks—whether it’s automating Jira updates, managing stakeholder communication, or organizing product context—and why traditional product management practices are no longer enough. Matvey shares insider insights on building flexible, scalable processes grounded in system thinking, plus practical tips on integrating version-controlled knowledge systems like Git for seamless collaboration. We break down the task framework—covering topics, agents, skills, and knowledge—and how it leads to resilient, autonomous product teams. You’ll explore how to turn AI agents into your internal helpers, how to identify bottlenecks before they slow you down, and why a strong structured context is key to impressive AI independence. If you’re a product leader eager to stay ahead of the AI revolution, you’ll understand why embracing these frameworks now can mean the difference between leading innovation or falling behind. Whether you’re beginning to adapt or already scaling AI within your organization, this episode helps you reimagine what’s possible: faster decision-making, sharper focus, and smarter product development pipelines. Don't miss it if you’re ready to turn AI into your biggest asset. Matvey Bryksin is the founder of Product Map, a community-driven platform that helps product teams master AI-powered management. His experience spans UX research, software engineering, and leading product teams at innovative companies, making him uniquely suited to guide you through the new frontier of product management. Perfect for product managers, engineers, and executives eager to leverage AI in their workflows—this episode will inspire you to think differently about process, organization, and growth in an AI-first era. Follow Us On: Spotify: https://open.spotify.com/show/1fTyX3TkUJTKgeonGWVMRC Substack - https://allstacks.substack.com/

    45 min
  2. The Surprising Role of Constraints in Accelerating AI-Driven Innovation With Curtis Sherbo

    Jun 2

    The Surprising Role of Constraints in Accelerating AI-Driven Innovation With Curtis Sherbo

    In This Episode of Stacked Sessions, Curtis Sherbo of Athena Health reveals a transformative approach to AI adoption by focusing on organizational efficiency and learning. In this episode, discover how a small, customer-focused team restructured their product and engineering strategies to prioritize flow over technology. By adopting 'Team Topologies' and fostering a culture of learning and prototyping, they achieved rapid innovation and outpaced larger competitors. Curtis shares insights on managing dependencies, embracing a product-oriented mindset, and empowering teams to experiment, offering a blueprint for leaders eager to drive meaningful change in the fast-evolving tech landscape. Follow Us On: Spotify: https://open.spotify.com/show/1fTyX3TkUJTKgeonGWVMRC Substack - https://allstacks.substack.com/

    38 min
  3. The Surprising Truth About AI in Software Development with Chris Condo

    May 19

    The Surprising Truth About AI in Software Development with Chris Condo

    The future of software engineering isn’t just about faster code—it's about smarter, AI-empowered workflows that reshape how teams build, test, and deliver value. In this episode with Chris Condo, a pioneer in value stream management, discover how AI-native Software Development Lifecycle (SDLC) transforms traditional tasks, making processes faster, safer, and aligned with business goals. Learn why simply adding AI tools isn’t enough and how creating a holistic context, establishing governance, and fostering the right team mindset unlock real speed. Explore strategies for integrating AI seamlessly into workflows, overcoming resistance, and measuring value over velocity. This episode is perfect for engineering leaders, product managers, and DevOps teams ready to leverage AI for maximum impact. Chris Condo, known for revolutionizing product delivery through innovative frameworks, shares insights on evolving roles in an AI-dominated landscape. Join us to reimagine what’s possible when humans and intelligent agents collaborate to build better software faster. Follow Us On: YouTube - https://www.youtube.com/@StackedSessions-Podcast Substack - https://allstacks.substack.com/

    41 min
  4. Platform Engineering In The AI Era: Bottlenecks, Agents, & What Actually Matters with Arthur Freyman

    May 5

    Platform Engineering In The AI Era: Bottlenecks, Agents, & What Actually Matters with Arthur Freyman

    Most companies are missing the huge opportunity AI offers for platform engineering and DevOps — but the shift in how we build and manage software is happening fast.In this episode, Jeff Kyes sits down with Arthur Freeman, Director of Engineering at ZipRecruiter, to explore how AI is transforming the very way we develop, deploy, and maintain software systems. Arthur shares insights from three decades of experience across Fortune 100s, startups, and SaaS, revealing why the traditional notions of coding, platform design, and even organizational culture are changing — often faster than we can keep up.Y ou’ll discover why the customer—for AI-powered platforms—is shifting from a human to an agent, and what that means for developer workflows and UI design. Arthur discusses how the principles of software reuse are evolving in an era where throwaway code and hyper-automation are the norm, challenging long-held beliefs about durability and reusability. We break down the critical bottlenecks that are intensifying with AI's velocity boost, and how frameworks like Dora and Space still matter for predicting performance—yet need to be augmented for AI-driven pipelines.This episode dives into the core challenges of externalizing organizational context to AI agents, preserving human feedback, and embedding preferences across systems—problems that are only going to grow more urgent. Arthur’s expertise offers a rare glimpse into the cultural and technical shifts that every engineering team must navigate to thrive in an AI-first future. If you're leading engineering at any scale, or building the next-generation platform, this episode is essential. It reframes your assumptions around automation, team collaboration, and the future of software delivery—arming you with the perspective to identify pitfalls before they happen, and opportunities that could define your success. Arthur Freeman is an experienced platform leader and security expert, deeply involved in the evolution of developer tools and AI. His insights illuminate a path through the chaos, showing how to adapt core principles to a radically new landscape.Ready to rethink how your teams build, decide, and lead? Tune in now to explore the future of software engineering in the age of AI. Follow Us On: YouTube - https://www.youtube.com/@StackedSessions-Podcast Substack - https://allstacks.substack.com/

    45 min
  5. From Building to Reviewing: The Evolution of Developer Roles in the Age of AI with Chris Heilmann

    Apr 29

    From Building to Reviewing: The Evolution of Developer Roles in the Age of AI with Chris Heilmann

    In this episode, Chris Heilmann explores the unexpected power of deleting outdated code as a strategy for future-proofing projects in an AI-driven world. As AI and large language models become central to software innovation, legacy code and bloated systems threaten security and performance. Chris explains why removing unnecessary code is now a competitive advantage and how it can rejuvenate your development process. Listeners will gain insights into combating the "AI slop" problem, overwhelming or malicious code, through practical tactics like PR limits and standardized testing. Chris shares advice for engineering leaders on fostering a culture where developers are empowered to delete excess, not just build. This episode is perfect for tech professionals looking to streamline, secure, and future-proof their codebase in a rapidly changing landscape. Follow Us On: YouTube - https://www.youtube.com/@StackedSessions-Podcast Substack - https://allstacks.substack.com/

    46 min
  6. The Shocking Truth: How AI Makes Code Cost Zero and Boosts Business Value with Duncan Grazier

    Mar 25

    The Shocking Truth: How AI Makes Code Cost Zero and Boosts Business Value with Duncan Grazier

    Unlock the future of engineering leadership in a world where the cost of code hits zero and AI transforms every line of work. Duncan Grazier, CTO at BuildOps, reveals how today’s CTO must wear multiple hats—blending technical mastery with business savvy—to stay ahead in this rapidly evolving landscape. Are you ready to lead the change or risk falling behind? In this episode, Duncan shares how AI is democratizing software creation, from enabling non-engineers to code effortlessly to reimagining the entire product and team structure. You’ll discover why traditional metrics like lines of code and effort are becoming obsolete and how framing engineering success in business terms, cost reductions, revenue growth, and retention, can unlock new opportunities. Duncan dives into practical strategies for managing exponential change, building guardrails over rigid rules, and shifting from reactive to proactive leadership in the AI era. Speaker: Duncan Grazier, CAIO at BuildOps https://www.linkedin.com/in/itsmeduncan/

    36 min
  7. The Hidden Power of Harness Engineering: Unlocking AI’s Full Potential in Your Teams with Vivek Haldar

    Mar 11

    The Hidden Power of Harness Engineering: Unlocking AI’s Full Potential in Your Teams with Vivek Haldar

    Most engineering leaders are still navigating the explosive shift from traditional development to AI-driven software creation. Vivek Haldar, a former Google AI expert turned indie innovator, explains the seismic changes reshaping coding — from autopilots to autonomous agents — and reveals how top teams are building "dark factories" to automate their entire SDLC. In this episode, Vivek shares practical frameworks on harness engineering and the role of skills, abstractions, and tooling in creating reliable AI agents. You'll discover the three key ideas redefining automation: groundings of MCP, workflow-following agents, and generative UI. Plus, learn why the rapid pace of model improvement demands constant recalibration and experimentation to stay ahead.

    35 min
  8. The Surprising Equation that Reveals Why 88% of AI Initiatives Fail to Scale with James Kaplan

    Feb 25

    The Surprising Equation that Reveals Why 88% of AI Initiatives Fail to Scale with James Kaplan

    In this episode of Stacked Sessions, I chat with James Kaplan, a partner at McKinsey & Company, about the surprising equation that explains why 88% of AI initiatives fail to scale. We delve into the complexities of AI-driven development, the disconnection between investment in technology and tangible business outcomes, and the often-overlooked factors like deadweight loss that hinder success. James shares insights on the evolving landscape of software engineering, emphasizing the need for a shift in mindset beyond productivity gains to a more strategic approach that aligns AI with business goals. Tune in as we explore how organizations can effectively navigate these challenges and drive meaningful change in their engineering practices.

    40 min
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About

Stacked Sessions is the podcast where software engineering meets business strategy. Hosted by Allstacks, each bi-weekly episode brings together executives, engineering leaders, and industry experts to explore how product and engineering drive measurable business impact. From ROI and board-level reporting to the future of AI in software delivery, we go beyond productivity to focus on what matters most: turning engineering investments into strategic advantage. Whether you’re a CTO, a C-suite executive, an executive member, or an aspiring executive—Stacked Sessions delivers the insights you need to connect code to capital.

Information

  • Creator
    Jeff Keyes
  • Years Active
    2025 - 2026
  • Episodes
    14
  • Rating
    Clean

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