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Stacked Sessions

Jeff Keyes
Artificial Intelligence
AI Agents
Platform Engineering
Product Management
Harness Engineering
Athena Health
AI In Software Development
Business ROI
Velocity and Reliability Metrics
Agile
Context / Tribal Knowledge
Code Generation
We Are Developers World Congress
Dora Metrics
Humans Vs Agents
Devops Culture
AI Native SDLC

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 m... more

PublishesTwice monthlyEpisodes13Founded8 months ago
Number of ListenersCategories
NewsTech NewsBusiness

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Artwork for Stacked Sessions

Latest Episodes

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 thei... more

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-... more

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 Z... more

In this episode, Chris Heilmann explores the unexpected power of deleting outdated code as a strategy for future-proofing projects in an AI-driven world.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 s... more

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 sa... more

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 autopi... more

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 disconne... more

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 lever... more

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Recent Guests

Curtis Sherbo
Product Leader for Patient Conversations
Athena Health
Episode: The Surprising Role of Constraints in Accelerating AI-Driven Innovation With Curtis Sherbo
Chris Condo
Client Partner at Equal Experts, former Forrester principal analyst, original author of the Forrester Wave that put value stream management on the map
Equal Experts
Episode: The Surprising Truth About AI in Software Development with Chris Condo
Arthur Freyman
Director of Engineering on the platform side at ZipRecruiter
ZipRecruiter
Episode: Platform Engineering In The AI Era: Bottlenecks, Agents, & What Actually Matters with Arthur Freyman
Chris Heilmann
Developer advocate, author, speaker, content curator, and moderator of the We Are Developers World Congress
We Are Developers / Microsoft (historical affiliation)
Episode: From Building to Reviewing: The Evolution of Developer Roles in the Age of AI with Chris Heilmann
Duncan Grazier
CTO at BuildOps
BuildOps
Episode: The Shocking Truth: How AI Makes Code Cost Zero and Boosts Business Value with Duncan Grazier
Vivek Haldar
Founder of Incaridian Labs / former VP of AI agents and distinguished engineer at Emergence AI
Incaridian Labs / Emergence AI
Episode: The Hidden Power of Harness Engineering: Unlocking AI’s Full Potential in Your Teams with Vivek Haldar
James Kaplan
Partner at McKinsey & Company advising CIOs/CTOs on technology strategy
McKinsey & Company
Episode: The Surprising Equation that Reveals Why 88% of AI Initiatives Fail to Scale with James Kaplan
Trevor Herr
Director of Engineering Applications at Syndio
Syndio
Episode: The Hidden Challenge of Measuring AI's Impact on Developer Productivity with Trevor Herr

Host

Jeff Kyes
Host of Stacked Sessions

Top Business Podcasts

Talking Points

Recent interactions between the hosts and their guests.

The Surprising Role of Constraints in Accelerating AI-Driven Innovation With Curtis Sherbo
Q: Can you like double click on that for a second?
Sherbo explains that the journey started with organizational constraints and an intentional shift from rigid processes to a discovery-led framework, emphasizing that efficiency and alignment came from understanding the current operating model, not from blindly applying AI tools; the focus was on learning, experimentation, and gradual change.
Platform Engineering In The AI Era: Bottlenecks, Agents, & What Actually Matters with Arthur Freyman
Q: What patterns are you seeing as roles collapse and product and engineering blur together in this AI-enabled landscape?
Teams are increasingly relying on surveys and value stream mapping to understand bottlenecks, while emphasizing direct observation of workflows and tacit knowledge that agents lack, to retain context and guide automation.
Platform Engineering In The AI Era: Bottlenecks, Agents, & What Actually Matters with Arthur Freyman
Q: How does this affect you as a platform guy? Could they just write some of this stuff and not need the platform anymore? How do you incorporate that?
The platform team still plays a crucial role in providing a shared infrastructure, consistency, and governance across diverse agents and environments, while enabling engineers to express constraints and maintain a unified delivery backbone.
The Surprising Equation that Reveals Why 88% of AI Initiatives Fail to Scale with James Kaplan
Q: What are the six imperatives for applying the right AI economics, and where should leaders start?
The six imperatives include maturing the product operating level, adopting a new talent model (spec-driven development), building semantic data layers, rethinking risk and governance, leveraging AI-assisted refactoring to reduce technical debt, and accelerating architecture to support scalable AI deployment.
The Surprising Equation that Reveals Why 88% of AI Initiatives Fail to Scale with James Kaplan
Q: What makes today different in the shift to AI-enabled development, and how big of a change might this be?
The guest argues that while past shifts (e.g., from assembler to high-level languages) were transformational, the current AI shift may be more systemic, requiring organizational redesign and cross-functional change rather than isolated improvements, with a potentially longer time horizon for ROI.

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Frequently Asked Questions About Stacked Sessions

What is Stacked Sessions about and what kind of topics does it cover?

Stacked Sessions explores how engineering leadership translates software delivery into measurable business value, with a strong emphasis on AI, platform engineering, and value-driven development. Recent episodes dig into AI-native SDLC, AI agents and harness engineering, platform-scale metrics, and new workforce dynamics as automation reshapes who does what in software delivery. The conversations tend to blend practical governance, ROI framing, and real-world case studies to help technical leaders articulate business impact, justify investments, and guide organizational change. A notable strength is the host trio's focus on actionable patterns, governance, and the intersection of technology decisions with business outcomes, making it a valu... more

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1. The AI Daily Brief: Artificial Intelligence News and Analysis

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Stacked Sessions launched 8 months ago and published 13 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Stacked Sessions?

Recent guests on Stacked Sessions include:

1. Curtis Sherbo
2. Chris Condo
3. Arthur Freyman
4. Chris Heilmann
5. Duncan Grazier
6. Vivek Haldar
7. James Kaplan
8. Trevor Herr

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