The Engineering Leadership Podcast

James Reggio, the CTO of Brex and a former engineer at Microsoft, Airbnb, and Stripe, dives into Brex 3.0—a bold operational evolution. He shares how a layoff sparked a rebirth, reshaping the company’s focus from a Series E to C mindset. Discover the innovative 'Hacker House' initiative, a startup within a startup aimed at AI disruption. Reggio discusses the introduction of seasonal initiatives for alignment and how shared roadmaps have boosted morale. His insights on balancing innovation within core operations are both enlightening and actionable.

Jonathan Raymond, founder and CEO of Ren and author of the award-winning book Good Authority, explores the complexities of modern management. He discusses the invisible cognitive load managers face and how AI can augment decision-making by enhancing field intelligence. Jonathan emphasizes the importance of human skills in leadership, highlighting how AI can support rather than replace these capabilities. He also offers actionable insights on fostering accountability and effective feedback, all while navigating team dynamics and performance levels.

Laura Tacho, CTO at DX and expert in engineering organization performance, dives into how many companies fall short in leveraging AI effectively. She argues that focusing solely on individual productivity doesn't yield organizational success. Laura emphasizes the importance of a systems-level approach to find high ROI and discusses how AI amplifies existing strengths and weaknesses. With insights on data literacy and strategic budgeting for 2026, she guides leaders to view AI as an opportunity for innovation rather than just a cost-saving tool.

Miriam Aguirre, Co-founder and CEO of Ingenimax, shares her insights on the evolving landscape of platform engineering. She discusses how natural language can transform interactions with infrastructure, shifting engineers from tactical tasks to strategic roles as curators. The conversation delves into the need for rapid onboarding, the balance between standardization and flexibility, and the role of human judgment in a world increasingly dominated by AI. Expect a fascinating look at the future of engineering leadership and hands-on innovation.

Chrystal Henke Ball, VP of Engineering at Yahoo, shares her insights from her extensive experience leading teams at Google and beyond. She discusses balancing current constraints with future possibilities, urging leaders to challenge assumptions and adapt architectures. Chrystal highlights the importance of grit in leadership, advocating for transparency and collaboration across product, engineering, and design teams. With practical strategies on cultivating resilience and leveraging AI for innovation, she emphasizes evolving workflows and maintaining focus on user impact.

Simone Kalmakis, VP of Engineering at Viam, has a rich background in AI, big data, and building healthy teams across tech industries. She shares her journey transitioning from health-tech to climate tech, emphasizing the application of leadership in mission-driven settings. Simone discusses how she prioritizes depth in managing teams, outlines her onboarding framework for new domains, and highlights innovative technology uses in everyday life to enhance experiences. Her insights provide a roadmap for navigating leadership across diverse technical challenges.

Ben Kus, CTO at Box, shares insights from his extensive career in engineering and AI strategy. He discusses the transformative potential of generative AI for enterprises and the need for a balanced technical vision that prioritizes innovation and security. Kus emphasizes the importance of a ‘multi-speed’ organization to foster agility while maintaining stability. He also delves into the challenges of integrating AI agents, touching on effective risk management and compliance, and highlights emerging trends in enterprise AI.

Engineering leadership is evolving, requiring a fresh approach to navigate the new landscape. Discover insights on the transformative role of AI and the essential skills for innovative teamwork. The upcoming conference promises personalized mentorship and community-building among leaders. Attendees will explore deep dives into companies like OpenAI and gain tactical frameworks to enhance their leadership. With a renewed focus on emotional intelligence and collaboration, this event is set to equip leaders for success in an ever-changing environment.

Michael Grinich, the founder and CEO of WorkOS, shares his innovative approach to product development where engineers take on responsibilities usually held by product managers and designers. He discusses the advantages of a flattened organizational structure and direct communication between developers and users. Grinich emphasizes the importance of user-centric thinking, adaptability, and cultivating curiosity within teams. Additionally, he highlights the role of tools like Model Context Protocol in revolutionizing software development, making coding more accessible to everyone.

Srinath Kuruvadi, a globally recognized cybersecurity executive and Managing Director at JPMorgan Chase, shares his insights on influencing without authority in engineering leadership. He discusses the importance of empathy, trust, and shared goals in building stakeholder relationships. Srinath highlights strategies for navigating challenges in collaborative environments and emphasizes the trend of integrating AI in security. His innovative ideas on operationalizing curiosity through The Innovation Lab show how to inspire teams and drive meaningful change in technology.