The Engineering Leadership Podcast

Andrew McNamara, Director of Applied Machine Learning at Shopify, leads the team behind Shopify Sidekick and builds production-scale AI assistants. He talks about Shopify’s prototype-first culture and how interns shape AI adoption. The conversation covers Sidekick’s merchant-driven vision, building ground-truth evals, subagent specializations, proactive features like Sidekick Pulse, and reliability and latency strategies.

Inbal Shani, Chief Product Officer and Head of R&D at Twilio, leads product, engineering, and R&D operations focused on platform strategy and customer experience. She discusses reorganizing R&D to follow strategy, using PRFAQs and working backwards, shifting from output metrics to time-to-value, measuring AI by behavior, and storytelling roadshows to drive company-wide transformation.

Rajat Monga, Corporate VP leading AI frameworks and edge inference at Microsoft and former TensorFlow co-founder, recounts scaling deep learning and founding Inference.io. He discusses refounding vs rebuilding systems, open source impact, startup pivots and hidden user incentives, and strategies for edge ML and large-scale inference infrastructure.

Murali Swaminathan, CTO at Freshworks with 30+ years in software engineering leadership, guides how large organizations operationalize responsible AI. He discusses architecture of predictability, engineering guardrails like kill switches and SDLC gates, agentic workflows versus deterministic flows, and the systems-thinking shift needed to scale trustworthy AI across thousands of customers.

Jon Hyman, CTO and co-founder of Braze, leads platform engineering with a focus on product health and AI roadmapping. He explains Braze’s quantitative product health scoring, how to align engineering with business outcomes, and a three-tier framework for AI features. Short takes cover reducing escalations, speeding time-to-value, and reorganizing teams to balance reliability and visionary innovation.

Sebastiano Armeli, an engineering leader at Meta with prior roles at Spotify, Snap, PayPal and Pinterest, shares frameworks for leading in product-, business-, and design-led companies. He discusses how leadership shifts with organizational incentives, how AI speeds prototyping and changes team structure, and the tradeoffs between metrics, intuition, and programmatic execution.

Lindsey Simon, VP of Engineering at Vercel and former Google core team member who helped launch App Engine, discusses live all-hands turned demo days for alignment and inspiration. He explores live visual demos for accountability, low-rehearsal demo tactics, his "vote with your wallet" career framework, the janitor mindset of prioritizing mission, and why building hobby projects keeps managers technically and empathetically sharp.

Chris Chiu, VP of Engineering at Salesforce who builds enterprise AI agents, shares career navigation wisdom. He talks about spotting energy mismatches, crafting a personal career thesis, and running a structured exploration phase. He explains the “Running Framework” for safe role change and why modern leaders must develop real technical depth in AI-led teams.

Sulman Choudhry, Head of ChatGPT engineering at OpenAI and former product lead at Meta and UberEATS, discusses how engineering teams evolve around missions. He covers fluid mission-driven teams, vertical vs horizontal structures, and the Directly Responsible Individual model. Conversations dive into coordinating many experiments, managers as systems designers, mentoring across levels, and scaling decision-making without bottlenecks.

Kiren Sekar, Chief Product Officer at Samsara and builder of a platform processing trillions of operational data points. He unpacks Samsara’s decade-long compound product strategy. He describes accelerating feedback loops, a 25-trillion-point data flywheel, and embedding engineers in frontline environments to spark customer-driven innovation.