In an era where AI delivers answers instantly, leadership is shifting from output to awareness. This article explores how curiosity, clarity, and connection become essential skills for engineering leaders who want to stay grounded in their own judgment—rather than outsourcing confidence to the machine.

Baaaaaaa.🐑 You’ve heard it before — the sound of teams moving fast but not forward. In the race toward AI, most leaders follow trends instead of realizing purpose.

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. 

At ELC 2025, what began as a discussion on defining outcome-oriented metrics for AI features turned into something more revealing: a shared struggle among engineering leaders to measure the real impact of AI-assisted work. This piece explores why teams often mistake productivity spikes for progress, the missing link between activity and outcome, and how to bridge that gap with metrics that actually matter.

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.