How do you apply your leadership skills to a new, mission-driven industry and effectively lead teams across multiple technical domains? In this episode, Simone Kalmakis (VPE @ Viam) shares her playbook for successfully transitioning between industries from health-tech and climate to her current work in robotics and AI. We deconstruct the leadership models she uses to prioritize her time, manage multiple technical experts, and why she focuses on "depth with 1-2 teams > breadth". Plus, her framework for onboarding in a new domain, the lifecycle of a leadership "deep dive," and communication practices that build trust and empower your entire organization to stay aligned and motivated.

"If we were building Box today, what would we do?” Ben Kus (CTO @ Box) deconstructs their playbook for enterprise AI innovation. We cover their journey to reimagine & reorient the company to a new technical vision, how they run a “multi-speed” org that balances startup agility and & enterprise-grade stability, and their “platform first” approach to build AI features. Ben also explains why security/compliance was foundational from "day negative one" in their AI strategy, the evolution of agentic AI, determining the right guardrails for AI agents & the future of multi-agent systems, enterprise trends & more. 

What if your engineering team didn’t just write code, but owned product discovery, wrote the launch messaging, and handled early sales? In this episode, Michael Grinich, CEO and founder of WorkOS, deconstructs their playbook for collapsing the product/engineering stack: no design leads, only one PM, and engineers who own product end-to-end. Michael breaks down how they teach product thinking, build with deep customer insight, and why his most important job is often to "cut scope." You’ll learn how to remove the "lossy translation layers" between teams, build a culture of curiosity and customer obsession, and ship higher-quality products, faster.

Influencing without authority is the hidden superpower of security leadership—and a crucial skill every engineering leader must master. In this episode, Srinath Kuruvadi (Head of Cloud Security @ JPMorgan Chase) breaks down how to influence without formal authority and advocate when ROI isn’t immediately clear. We cover tactics for shaping problems from the POV of other stakeholders, Plus, strategies to establish shared outcomes, insights on optimizing your time, emerging AI x security trends, and how his team is operationalizing curiosity & experimentation through The Innovation Lab.

John Amaral (CTO and co-founder @ Root.io) joins us to discuss the evolving role of engineering leaders and why vision-first leadership & building your “vision” muscle is more critical than ever. We dive into why “shift left” is dead and why SaaS is being replaced by “do-it” as a service. John also unpacks how to think in outcomes, apply the Jobs-To-Be-Done framework to eliminate toil, and reimagine product experiences. Plus, we look inside Root.io’s approach to building AI-native security products that ship daily. Whether you’re rethinking your org design or exploring the frontier of AI-powered engineering, this episode will reshape how you think about building, leading, and scaling teams.

What does it take to operate with startup-level speed… in one of the most complex, high-stakes industries on the planet? In this episode, we go inside Commure’s engineering org w/ Dhruv Parthasarathy (CTO @ Commure & Athelas). We cover how to push decision-making down to move faster and reduce risk, structure teams for rapid iteration, and turn customers into product co-creators. Dhruv also shares how they cultivate polymath capabilities across EPD to accelerate velocity, why scope is one of the most underrated sources of leverage in engineering, and the frameworks they use to identify compound wins. If you’re scaling an eng org, leading in a complex domain, or designing your team for speed—this episode is packed with tactical frameworks you can apply immediately.

How do you lead a high-velocity engineering team—when everything about how we build is changing? How do you cultivate more of a product mindset in your engineering teams? Loïc Houssier (VP Engineering @ Superhuman) shares his evolving playbook for driving velocity in eng orgs today, building product-minded teams, and cultivating product taste. We cover leading culture / mindset transformation, creating exceptional product experiences, operational excellence when product quality is increasingly subjective. Plus the evolution of productivity tools!

When Nissim Lehyani (VP of Product at Life360) used AI to build a math game for his son, he didn’t just prototype a game, he rewired how he thinks about product development and the relationship between engineering, product, and design. In this episode, Nissim shares how that personal “aha” moment sparked a shift in how his teams build, collaborate, and ship. We dive into how AI is accelerating product iteration from months to hours, why it’s time to drop the “M” from MVP, and how prototypes are replacing PRDs as the central artifact of product work. Plus how product rituals and building cadence are evolving, strategies for scaling a prototype-first workflow, and we deconstruct the “lightning pod” model and how it’s changing the dynamics of product building & EPD collaboration.

How do you go from deeply technical IC to leading 100+ engineers - and still stay close to the tech? Prashant Ramarao, SVP of Engineering & Head of AI @ Yahoo shares lessons from his unconventional leadership journey, exploring the mindset shift from expert IC to executive! We cover how to scale your leadership while maintaining technical credibility and how to effectively communicate with GMs & other non-technical stakeholders. Plus, Prashant shares personal AI projects that enhanced his technical credibility, leadership skills & understanding of how to integrate AI into products If you’re navigating the leap from technical to strategic, or scaling your leadership, this one’s for you.

AI is reshaping the fundamental economics of startups—lowering product development costs, compressing GTM cycles, and rewriting the rules of competition. In this episode, Craig McLuckie (Co-Founder & CEO @ Stacklok, co-creator of Kubernetes) unpacks “the epoch of the startup,” a moment of massive disruption where fast-moving founders have a unique edge over incumbents. We explore how Craig is navigating this new era from rethinking cost structure, value capture, and defensibility to leveraging open-source, community, and asymmetric advantages as core pillars of Stacklok’s strategy. Craig shares lessons from pivotal product shifts, frameworks for identifying moats, and the broader societal implications of AI-driven disruption. Whether you’re leading a startup, pivoting in the face of AI, or thinking about your next big move, this conversation offers a strategic playbook for thriving in today’s shifting landscape.