This is a special episode, highlighting a session from ELC Annual 2025! Bill Coughran (Partner @ Sequoia Capital & former SVP of Engineering @ Google) and Bret Reckard (Talent Partner @ The General Partnership) deconstruct the evolving role of engineering leadership in an era dominated by AI hype. Bill is a legendary leader who joined Google right after the .com bubble and has seen every major industry shift since. Drawing on his experience scaling Google and advising world-class startups, Bill shares why the best leaders are "catastrophic thinkers," how to balance servant leadership with the need for decisive action, and why AI is forcing every leader to return to their technical roots. Plus they cover enduring companies and real value capture in the AI era, the nuances of organizational design, the "apprentice model" for mentorship and the dangers of over-layered hierarchies that stifle speed. Bill also provides a candid look at leadership transitions, offering a tactical guide for those moving from Big Tech to early-stage startups.

This is a special episode, highlighting a session from ELC Annual 2025! OpenAI evolved from a pure research lab into the fastest-growing product in history, scaling from 100 million to 700 million weekly users in record time. In this episode, we deconstruct the organizational design choices and cultural bets that enabled this unprecedented velocity. We explore what it means to hire "extreme generalists," how AI-native interns are redefining productivity, and the real-time trade-offs made during the world's largest product launches. Featuring Sulman Choudhry (Head of ChatGPT Engineering) and Samir Ahmed (Technical Lead), moderated by Lawrence Bruhmeller (Eng Management @ Sigma).

In this episode, Brian Balfour (Founder & CEO @ Reforge) deconstructs the two core, interconnected challenges leaders face in the AI age: deciding what to build and evolving the Engineering, Product, Design workflow to deliver it. We cover why you should avoid “the local maxima trap” and siphon off "skunkworks" teams to take high-risk, AI-native bets. Brian provides the blueprint for the "Great Distribution Shift," detailing how to reshape your product from the ground up to avoid being left behind as platforms close, and how to emerge as a winner in the new AI landscape. Plus, learn how to rethink what to build, avoid commoditization, compress product discovery from weeks to hours, scale feature variations & prototypes, evolve products to solve harder classes of problems and shift specialist roles from "inboxes" to system builders.

Rajeev Rajan (CTO @ Atlassian) shares the leadership playbook he used to transform Atlassian’s engineering culture, and how that cultural foundation directly powered the build and launch of Rovo (Atlassian’s new AI powered app). We cover how they reduced ship time from 120 days to zero, why “developer joy” is the metric that matters, and how to create a community of developer productivity champions to scale DevEx transformation. Rajeev also breaks down his principles for systematizing autonomy and empowerment, including frameworks for giving direct reports more ownership. Plus, a look at the future of Atlassian’s “Systems of Work”!

In this episode, Daniel Lereya (Chief Product and Technology Officer @ Monday.com) shares how they are evolving their engineering roles from developers to builders & system designers, where the lines between product, engineering, and design are intentionally blurred, and developers manage AI Agents as team members, tackling an ever-expanding list of projects. We explore the shift from "developer" to "system designer" and why managing AI agents requires the same skills as managing people. Plus, a case study where the Monday.com team leveraged AI agents to decompose a monolith, autonomously manage the project board and assign strategic / high-risk tasks to humans.

This is a special episode, highlighting a session from ELC Annual 2025! The true promise of AI isn’t in replicating human intelligence. It’s in developing entirely new forms of non-human intelligence that perceive and understand the world in fundamentally different ways. Jamie Lien (Co-Founder and Chief Scientist @ Archetype AI) and Rashi Agarwal (Head of AI Engineering @ GoodLeap) explore the emergence of "Physical AI" - machines that sense the world through modalities beyond human biology to form internal representations free from our biases. This means building machines that can directly sense the physical world through modalities beyond human biology, form their own internal representations and interpretations free from our biases, and then translate that understanding back to us in human terms.

Ruslan Belkin (Head of Platform Engineering @ Inflection AI) joins us to deconstruct fundamental shifts in engineering leadership. We explore the future of user interfaces, his “sci-fi” approach to establish & test product vision, & how to leverage “investor decks” for better decision-making and project validation. Ruslan also dives into the complexities of building emotional intelligence into AI systems, cultivating an outcome-oriented engineering culture & avoiding process traps. Plus, we discuss how to keep up with the velocity of change (including when new research necessitates a major pivot), synthetic data & the future of data as a defensibility strategy, & why agent reliability is the massive opportunity ahead. 

James Reggio (CTO @ Brex) shares the story of "Brex 3.0", an 18-month journey behind their operational evolution. We explore how they rewound their org from a Series E to a Series C mindset, and replaced siloed OKRs with seasonal "marquee initiatives." James deconstructs the “Brex Hacker House”, an AI-focused startup within a startup experiment aimed to disrupt their core business. This conversation is all about evolving operational rhythms, layers of management, product building, and culture change!

Jonathan Raymond is the Founder and CEO of Ren, an AI agent for managers and teams that helps them give and receive feedback, have meaningful 1:1s, and access real-time personalized coaching. He is also the author of the award-winning book Good Authority and was named one of Inc. Magazine’s Top 100 Leadership Speakers. Previously the CEO of EMyth, Jonathan has led transformation projects across technology, renewable energy, and coaching. He’s a half-decent barista, a mediocre-but-enthusiastic surfer, and will never give up on the New York Knicks.

Businesses are spending millions on AI tools hoping to accelerate time-to-market but aren't seeing organizational-level results. Laura Tacho (CTO @ DX) explains why an "individual productivity" mindset fails and how AI merely accelerates the condition of the system it enters. She provides a framework for leaders to shift to a systems-level approach, find high-leverage ROI by looking outside the 20% of time spent coding, and understand what sets high-ROI orgs apart. Plus Laura shares data literacy tools to cut through the "whiplash" of conflicting AI reports and provides key considerations for 2026 budgeting, detailing where and how companies are planning to strategically invest.

What happens to platform engineering when natural language becomes the primary interface to infrastructure? Miriam Aguirre (Co-founder & CEO @ Ingenimax) joins us to explore how AI is fundamentally reshaping platform strategy, team structures, and the very role of the platform engineer. We deconstruct the shift from tactical "how" to strategic "why" and explore what it means to lead and build resilient systems in this new paradigm.

In this episode, we’re addressing one of the biggest challenges current eng leaders are facing – balancing yesterday’s constraints with tomorrow’s potential! Chrystal Henke Ball (VP of Engineering @ Yahoo) shares insights on why it’s important to constantly challenge your assumptions and how vision can sometimes work as a bottleneck for your organization. We dissect how the traditional product lifecycle is evolving to become more fluid and what that means for the collaborative relationship between product, eng, and design. Additionally, Chrystal defines grit, why it’s important for leaders to model it, and strategies for cultivating the trait within your eng team in order to move past short-term challenges and focus on long-term goals!

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. 

Engineering leadership is undergoing a seismic shift, requiring playbooks to be rewritten, in real-time. In this special episode, hosts Patrick Gallagher and Jerry Li give you an inside look at the ELC Annual 2025 experience, and how the two-day conference will equip you with new mental models, skills, and frameworks required to lead. Get a preview of tactical takeaways from deep operational dives into companies like OpenAI, Amplitude, and HeyGen. Discover how the conference will help you redesign your innovation engine, transform your team's workflows, and blur the lines between engineering, product, and business to drive impactful change. Through a unique mix of tactical sessions, peer-led roundtables, and curated mentorship, you'll learn how to find the community and coaching needed to lead through uncertainty and invest in your own career growth.

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.

We’re pausing the pod this week as we gear up final planning for ELC Annual 2025 - the premier event for engineering leaders. New episodes return next week (on a biweekly schedule!). This is our biggest event of the year… 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections! We’d love for you to join us. 🎟️ Early Bird pricing ends soon – secure your spot at the best rate. 🔗 Get your ticket now → https://sfelc.com/annual2025

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.