In this episode, Geddes Munson (SVP of Engineering @ Affirm) joins us to discuss operational / engineering excellence, scaling, and AI-native transformation! We explore Affirm’s approach to operational and engineering excellence and how a 2024 outage became a turning point in refining that focus. We deconstruct “AI retooling week”, the internal tools it inspired (including an incident tracing system), how the AI-native transition is impacting operational / engineering excellence, and how to connect these projects to business goals. Plus, we take a look at their early work building in agentic commerce, infrastructure decisions they made years ago setting them up for success now, how they’re thinking about designing for agent-first experiences.

Andrew McNamara, Director of Applied Machine Learning @ Shopify, joins the ELC podcast to share insights on building agentic platforms at scale, like Sidekick, that must keep reliability for its users at the forefront. Andrew describes the building philosophy behind Shopify and what it means to cultivate a culture of prototype-first while prioritizing hiring early-stage talent. We cover Sidekick’s development journey and how user feedback impacted its product vision, why evaluation is so important for determining ground truth sets, and the benefit of user-driven use cases. Andrew also dissects how they went about making product design decisions, such as building proactive agents and identifying subagent specializations. 

Inbal Shani (CPO and Head of R&D @ Twilio) deconstructs the transformation of the R&D org at Twilio! We explore the shift from a GM-led model to a unified platform strategy and “why structure must always follow strategy.” Inbal shares her framework for moving from output-focused metrics to input goals, prioritizing “time-to-value,” and the nuances of measuring AI products. We discuss using "R&D roadshows" as a strategic company transformation tool and why engineering leaders must master product positioning. We also dive into mental models for future-proofing your business, from "working backwards" to solve customer problems, to embedding systems thinking into the DNA of your engineering team, and critical questions to identify and optimize decisions around your company’s moat. 

Rajat Monga, CVP AI Frameworks @ Microsoft, joins the podcast to discuss his leadership and founder journey, from Google Brain / Tensorflow to [inference.io](http://inference.io/) and back to Microsoft. He dissects what it means to refound vs. start from scratch, the value of the open source community, and strategies for discovering what problem to solve when going the startup route. We also cover how to determine your users’ hidden incentives and what that means for both product development & marketing, along with navigating the balance between a product’s usefulness and consumers’ willingness to pay for it. Additionally, Rajat shares about what he’s currently up to at Microsoft and the emerging ML / AI technologies he’s most excited about. 

Enterprise customers demand 99.9% availability, regardless of how the underlying software is built. In this episode, Murali Swaminathan (CTO @ Freshworks) discusses how enterprises actually win with AI! We explore the “Architecture of Predictability” – proactive architectural safeguards to scale “responsible AI by design” across a global organization serving 75,000 customers. Murali shares his leadership playbook for implementing the technical safeguards and product trust controls that empower hundreds of engineers to build safely. We also dive into the shift from deterministic flowcharts to “workflows with a brain” and why backend systems engineers are the secret bedrock of agentic products. Plus, Murali deconstructs the dual evolution required of modern leaders: mastering strategic thinking at the business level while cultivating systems thinking at the engineering level.

Jon Hyman (CTO & Co-Founder @ Braze) returns to the podcast to share how he balances a mature, public-company roadmap with visionary AI innovation! We deconstruct Braze’s quantitative "Product Health" framework - a scoring system used to resolve competing prioritizations and mandate technical remediation. We also discuss shifting engineering leaders to think like GMs, how to realign teams by connecting abstract “vision” to specific releases, goals & outcomes. Plus, Jon’s three-tier mental model for AI products, how to identify AI features that actually drive revenue, and reimaging your product for future channels, teams and skills.

We discuss what effective leadership looks like across three organizational archetypes: product-led, business-led, and design-led companies with Sebastiano Armeli (Engineering Leadership @ Meta). Drawing from his leadership journey at places like  Meta, Spotify, Snap, and PayPal, Sebastiano deconstructs the situational leadership frameworks required to thrive in different environments. Plus we discuss how AI is moving managers from implementation to architecture, why the next bottleneck is managing the overhead of high-velocity experimentation, and the future of team topology where AI enables a single leader to oversee high-scale teams of 30–50 people. Whether you are scaling a design-driven startup or navigating a complex business-led enterprise, this conversation provides a framework for aligning your leadership style with your organization's core incentives.

Live from the Vercel recording studio, Lindsey Simon (VP Engineering @ Vercel) joins us to deconstruct the evolution of management craft and career growth strategies! We dissect the practice of live all-hands demos as a tool for context, accountability and inspiration. Plus, Lindsey’s "vote with your wallet" framework for career strategy, how Lindsey’s open source project inspired him to apply to Vercel, and why the most effective VPs are building hobby projects to maintain AI competency and empathy for non-technical users. 

Career progression is rarely a straight line. More often, it only makes sense in hindsight. Chris Chiu (VP of Engineering, Agentforce @ Salesforce) joins us to deconstruct how to navigate these non-linear career paths! We talk about identifying the mismatch in your current role, building a personal "career thesis," how to engineer a productive exploration phase and leverage your relationships / VC networks to understand the market. Plus, how to apply the "Running Framework" to ensure success in your next role and why technical depth is no longer optional for modern engineering leaders.

In this episode, recorded live at the OpenAI studio, Sulman Choudhry (Head of ChatGPT @ OpenAI) pulls back the curtain on how they structure engineering teams! We talk about shifting from silos to fluid mission-driven teams, vertical vs. horizontal teams, maximizing cross-functional collaboration between research, engineering, product and design. Plus we cover “directly responsible individuals” for high accountability, managers as systems designers, scaling decision-making to prevent leadership from becoming bottlenecks, frameworks for mentoring junior engineers, why “problem framing” is the most critical skill, and how managers can stay close to problems and maintain technical intuition.