Stacked Sessions

About Stacked Sessions

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.

Publisher

Jeff Keyes

Category

business · news

Language

en

Explicit

No

First episode

17 Oct 2025

Latest episode

2 Jun 2026

Latest episodes

13 episodes in the feed.

1. 

   2 Jun 2026

   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/

2. 

   19 May 2026

   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/

3. 

   5 May 2026

   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/

4. 

   29 Apr 2026

   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/

5. 

   25 Mar 2026

   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/

6. 

   11 Mar 2026

   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.

7. 

   25 Feb 2026

   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.

8. 

   12 Feb 2026

   The Hidden Challenge of Measuring AI's Impact on Developer Productivity with Trevor Herr

   The era of AI in software development is transforming faster than ever—and most teams are still just scratching the surface. Trevor Herr, Director of Engineering at Syndio, reveals how teams can shift from simply trying out AI tools to actually leveraging them as full-fledged agents that autonomously complete complex workflows. This isn’t about basic automation—it's about redesigning your entire approach to coding, testing, and deploying with AI as a true partner. In this episode, Trevor shares eye-opening insights on how AI moved from “glorified search” to powerful agents capable of end-to-end task execution. You’ll discover how the rapid evolution of agent tools like code fixers and refactors in 2024 is just the beginning of a new paradigm—one where engineers become managers of intelligent agents rather than sole creators of every line of code. He breaks down concrete frameworks for integrating these tools seamlessly into your workflow, emphasizing the importance of environment setup, team collaboration, and continuous feedback to avoid pitfalls like inefficiency and code quality issues.

9. 

   20 Jan 2026

   Alok Nandan: An Investor's Take on AI's Impact on Engineering

   In this episode of Stack Sessions, Jeff Keyes hosts Alok Nandan, a general partner at First Ventures, to provide an investor's perspective on the intersection of software engineering and business strategy. They delve into the impact of AI on engineering organizations, the importance of AI adoption, and the evolving role of software engineers. Key topics include Jevons paradox, day zero vs day two tools, and change management in AI adoption. Alok LinkedIn- https://www.linkedin.com/in/aloknandan First Rays VC - https://www.firstraysvc.com/

10. 

    23 Dec 2025

    Navigating the AI Revolution: Insights from Industry Leader Chris Condo

    Join Jeff Keyes and Chris Condo as they delve into the transformative impact of AI on software development and business strategy. Discover how AI is reshaping engineering processes, the challenges of measuring its impact, and the future of value stream management. Whether you're an industry veteran or new to the field, this episode offers valuable insights into leveraging AI for maximum value delivery. Tune in to explore the evolving landscape of software delivery and the role of AI in driving innovation. If you are interested in learning more about Equal Experts or connecting with Chris Condo: https://www.equalexperts.com/ https://www.linkedin.com/in/christophercondo/

11. 

    20 Nov 2025

    AI & Value Streams: Danny Presten's Blueprint for Tomorrow

    In this episode of Stacked Sessions, I have the pleasure of speaking with Danny Preston, an expert in value stream flow and enterprise software. Together, we explore the intersection of AI and software development, discussing how organizations can optimize flow and reduce bottlenecks. Danny shares his journey from industrial engineering to software delivery, drawing parallels between manufacturing principles and modern software practices. We delve into the current state of AI adoption in the industry, addressing both its promise and challenges. Danny also highlights the importance of understanding investment value in software projects, emphasizing the need for effective metrics and insights. Join us as we uncover practical strategies for leveraging AI to enhance software delivery and drive business success.

12. 

    4 Nov 2025

    Empowering Women in Tech: A Conversation with Jossie Haines

    Join us as we dive into an inspiring conversation with Josie Haines, a trailblazer in tech leadership. Discover her journey from engineering at top companies to empowering women in tech through coaching and advocacy. Learn about her unique approach to leadership, the importance of diversity, and how AI is reshaping the industry. LinkedIn: https://www.linkedin.com/in/jossiemann Website: https://jossiehaines.com YouTube: https://www.youtube.com/@jossiehaines Guide: 4 AI Workflows Every Engineering Leader Should Automate: https://jossiehaines.com/ai-workflows-engineering-leaders/ Leadership Impact Lab for Engineering Leaders: https://jossiehaines.com/engineering-leadership-coaching/

13. 

    17 Oct 2025

    Engineering Joy: The Future of Work with AI and Flow with Helen Beal

    In this inaugural episode of Stacked Sessions, I welcome Helen Beal, CEO of Flowtopia, to explore the intersection of AI and organizational flow in the evolving landscape of work. We discuss the importance of embracing AI to enhance productivity while eliminating friction in teams. Helen shares insights on how engineering leaders can shift from merely justifying their roles to owning and optimizing their value streams. We also delve into how Flowtopia fosters a vibrant community for practitioners to share experiences, learn best practices, and drive meaningful change. Join us as we uncover the pathway to creating joyful work experiences through innovative strategies and a focus on flow.

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