The Engineering Leadership Podcast

It started with a simple idea from James Tyack: “What if we hosted a hackathon at ELC Annual?” The result was a unique experiment where 14 senior engineering leaders stepped away from strategy to build and ship functioning apps in one weekend, unlocking new insights on AI-native workflows, "vibe coding," and the future of engineering. In this episode, we deconstruct the entire hackathon operational playbook, sharing lessons on everything from “best failure awards” and async collaboration structures to structuring ideation periods for maximum business alignment. Beyond the logistics, we explore how getting hands-on helped these leaders overcome imposter syndrome and why "rolling up your sleeves" is now a prerequisite for leading effective engineering teams. Plus, James shares how he plans to evolve the hackathon format at ELC and beyond. If you’ve been curious about leveraging hackathons to drive innovation, expose your team to new tools, or evolve how your org builds, this episode provides the blueprint for successful implementation. ABOUT JAMES TYACKJames is an engineering manager with a passion for people, technology, and learning. He's built and led distributed, diverse teams of engineers across locations and timezones for 10 years. James believes strongly in the value of diversity and championing a sense of belonging for everyone, from day 1. He's well versed in growth strategy, chaos engineering, major incident response, and blameless practice, and culture grounded by trust and psychological safety. He leads the Growth Acquisition team at Coursera where he's proud to be part of an organization that's transforming lives through learning. Previously, James enjoyed building and leading the Growth and Integrations engineering teams at PagerDuty. This episode is brought to you by Span!Span is the AI-native developer intelligence platform bringing clarity to engineering organizations with a holistic, human-centered approach to developer productivity.If you want a complete picture of your engineering impact and health, drive high performance, and make smarter business decisions…Go to Span.app to learn more! SHOW NOTES:The results of ELC’s first-ever hackathon: 14 leaders shipping fully functional apps (2:21)The “Scrappy” beginning: Extending the invitation and early community engagement (4:50)The most surprising insights: Problem solving for “life outside of work” and micromanaging AI agents (5:42)Navigating the shifting boundaries between product, engineering, and management roles (8:43)James’ personal journey: Building 5 apps in 5 hours to stay relevant and relatable (10:05)Deconstructing the Hackathon structure: The “Take-Home Assignment” approach (16:16)The Hall of Fame: Creating artifacts to recognize contribution (18:00)Iterating on the format: Pivots made for the next hackathon iteration at Coursera (18:47)The importance of a 2-week ideation period for alignment (20:59)A recap of the playbook: Seeding ideas, easy tooling, and safe deployment (22:15)The future of hackathons: Cross-functional participation beyond engineering (26:46)Rapid Fire Questions (28:15) This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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. ABOUT BILL COUGHRANBill Coughran works as a founders' coach and partner at Sequoia Capital to help build spectacular technology-centric companies. Previously, Bill was Senior Vice President of Engineering at Google with oversight of Chrome, YouTube, maps, google.com, underlying infrastructure systems, and security.ABOUT BRET RECKARDBret Reckard is Talent Partner at The General Partnership (TheGP), a hands-on venture firm working alongside ambitious founders in talent, engineering, go-to-market, and product. He leads TheGP’s Talent vertical, matching foundational leaders, early engineers, and key specialists across the portfolio. Before this role, Bret spent over a decade at Sequoia Capital leading Talent and Network, where he helped hundreds of founders at companies like Stripe, Confluent, Retool and DoorDash build their early teams. This episode is brought to you by Span!Span is the AI-native developer intelligence platform bringing clarity to engineering organizations with a holistic, human-centered approach to developer productivity.If you want a complete picture of your engineering impact and health, drive high performance, and make smarter business decisions…Go to Span.app to learn more! SHOW NOTES:Introduction and Bill Coughran's background at Sequoia and Google (1:36)Hiring pitfalls and the biggest mistakes made as a leader (3:49)Managing crises: Acting as a dictator during the 2010 Google hack (5:25)Building for the AI world without chasing "shiny objects" (7:09)Developing context: How to learn AI without relying on LLM summaries (9:02)Identifying enduring companies and real value capture in the AI era (10:53)The debate on coding assistants and the future of junior engineering talent (13:23)Transitions: Making the leap from large organizations to early-stage startups (15:59)Staying curious and finding excitement in the next professional challenge (18:23) LINKS AND RESOURCESLink to the video for this sessionLink to all ELC Annual 2025 sessions This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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). ABOUT SULMAN CHOUDHRYSulman leads ChatGPT Engineering at OpenAI, driving the development and scaling of one of the world’s most impactful AI products. He pushes the boundaries of innovation by turning cutting‑edge research into practical, accessible tools that transform how people interact with technology. Previously at Meta, Sulman founded and scaled Instagram Reels, IGTV, and Instagram Labs, and helped lead the early development of Instagram Stories.He also brought MetaAI to Instagram and Messenger, integrating generative AI into experiences used by billions. Earlier in his career, Sulman was on the founding team that built and launched UberEATS from the ground up, helping turn it into a global food delivery platform. With a track record of marrying technical vision, product strategy, and large‑scale execution, Sulman focuses on building products that meaningfully change how people live, work, and connect.ABOUT SAMIR AHMEDSamir is the Technical Lead for ChatGPT at OpenAI, where he currently leads the Personalization and Memory efforts to scale adaptive, useful, and human-centered product experiences to over 700 million users. He works broadly across the OpenAI stack—including mobile, web, services, systems, inference, and product research infrastructure.Previously, Samir spent nine years at Snap, working across Ads, AR, Content, and Growth. He led some of the company’s most critical technical initiatives, including founding and scaling the machine learning platform that powered nearly all Ads, Content, and AR workloads, handling tens of billions of requests and trillions of inferences daily.ABOUT LAWRENCE BRUHMELLERLawrence Bruhmuller has over 20 years of experience in engineering management, much of it as an overall head of engineering. Previous roles include CTO/VPE roles at Great Expectations, Pave, Optimizely, and WeWork. He is currently leading the core query compiler and serving teams at Sigma Computing, the industry leading business analytics company.Lawrence is passionate about the intersection of engineering management and the growth stage of startups. He has written extensively on engineering leadership (https://lbruhmuller.medium.com/), including how to best evolve and mature engineering organizations before, during and after these growth phases. He enjoys advising and mentoring other engineering leaders in his spare time.Lawrence holds a Bachelors and Masters in Mathematics and Engineering from Harvey Mudd College. He lives in Oakland, California, with his wife and their three daughters. This episode is brought to you by Span!Span is the AI-native developer intelligence platform bringing clarity to engineering organizations with a holistic, human-centered approach to developer productivity.If you want a complete picture of your engineering impact and health, drive high performance, and make smarter business decisions…Go to Span.app to learn more! SHOW NOTES:From research lab to record-breaking product: Navigating the fastest growth in history (4:03)Unpredictable scaling: Handling growth spurts of one million users every hour (5:20)Cross-stack collaboration: How Android, systems, and GPU engineers solve crises together (7:06)The magic of trade-offs: Aligning the team on outcomes like service uptime vs. broad availability (7:57)Why throwing models "over the wall" failed and how OpenAI structures virtual teams (11:17)Lessons from OpenAI’s first intern class: Why AI-native new grads are crushing expectations (13:41)Non-hierarchical culture: Using the "Member of Technical Staff" title to blur the lines of expertise (15:37)AI-native engineering: When massive code generation starts breaking traditional CI/CD systems (16:21)Asynchronous workflows: Using coding agents to reduce two-hour investigations to 15 minutes (17:35)The mindset shift: How rapid model improvements changed how leaders audit and trust code (19:00)Predicting success: "Vibes-based" decision making and iterative low-key research previews (20:43)Hiring for high variance: Why unconventional backgrounds lead to high-potential engineering hires (22:09) LINKS AND RESOURCESLink to the video for this sessionLink to all ELC Annual 2025 sessions This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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. ABOUT BRIAN BALFOURBrian Balfour is the Founder & CEO of Reforge, which provides expert training and tools for AI-native product teams. Previously, he served as VP of Growth at HubSpot, spearheading launches like HubSpot CRM and building the growth team that propelled the company’s next chapter. This episode is brought to you by Span!Span is the AI-native developer intelligence platform bringing clarity to engineering organizations with a holistic, human-centered approach to developer productivity.If you want a complete picture of your engineering impact and health, drive high performance, and make smarter business decisions…Go to Span.app to learn more! SHOW NOTES:Brian’s reaction to the 5:1 gap between AI coding usage and actual product quality challenges (1:57)Why your system only goes as fast as the slowest part, and how hyper-optimizing engineering moves bottlenecks elsewhere (4:53)The "Local Maxima" trap: Why turning designers and PMs into mediocre developers is a waste of opportunity cost (6:04)Siphoning off "Skunkworks" Teams for AI-Native Innovation (7:53)Moving from exploring two solution paths to ten by simulating "product reps" through AI prototyping (13:24)Reforge’s AI-native suite (Build + Research): Scaling prototypes, feature variations and compressing product discovery & validation from weeks to hours (15:43)Case Study: How Captions evolved to solve harder classes of problems, using a creator-tool wedge to fund custom AI emotion-models for the media studio market (19:54)Case Study: How Shopify reframed support agents as multimodal "Business Advisors" to provide outsized value (22:24)Navigating the great distribution shift: Understanding the lifecycle from open platforms to closed ecosystems (25:10)The lifecycle of distribution shifts: Navigating the "Open Phase" growth to "Closed Phase" monetization w/ examples from Facebook, Google, and Apple (29:30)OpenAI, memory & context as moat, and why you need to reshape your product from the ground up to win in this distribution shift (31:16)Strategic de-risking for EPD leaders: Building proprietary moats through memory, context, and specialized workflows (32:51)Optimizing EPD workflows and structures: Separate high-risk "skunkworks" from core product optimization, lean cross-functional teams for faster iteration / decisions, and avoiding too many specialized roles (35:25)Dissolving the "Octagon of Specialists": Shifting researchers and PMMs from "inboxes" to builders of self-serve systems (36:57)The five types of product work and why there is no "one-size-fits-all" system for EPD (41:25)Rapid fire questions (43:25)LINKS AND RESOURCESAbout Reforge: Expert training & AI-powered tools for product teamsReforge Build: The prototyping tool discussed for exploring multiple feature variations without designer constraints.Reforge Research: The AI-interviewer tool used to compress user discovery and validation from weeks to hours.Reforge Insights: The platform that aggregates qualitative customer feedback into a self-serve system for EPD teams.Brian Balfour’s Research & FrameworksBrianBalfour.com: Brian’s personal blog featuring deep dives into growth and product strategy.The Next Great Distribution Shift: The foundational article explaining the lifecycle of open vs. closed platforms.The Four Fits Framework: A refresher on the system of Product-Market Fit, Product-Channel Fit, Channel-Model Fit, and Model-Market Fit.Reforge Strategic Deep DivesAI Disruption Risk Assessment: A guide for engineering leaders to determine if their product is at risk of being commoditized.Product-Market Fit (PMF) Collapse: How to identify and avoid the risk of your core product losing relevance in the AI era.MentionsInvest Like the Best podcastThis episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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”! ABOUT RAJEEV RAJANRajeev Rajan is the Chief Technology Officer (CTO) at Atlassian. Rajeev joined the company in May 2022 and is responsible for Atlassian Engineering, IT, Security and Trust, and the Engineering Operations teams. His focus areas include the company's continued transformation to Cloud, Developer Platform, and Product lines. Additionally, he is passionate about continuing to develop Atlassian’s world-class engineering organization and making it a top choice for aspiring engineering talent worldwide.A long-time resident of Washington state, Rajeev previously acted as the Vice President and Head of Engineering for Facebook and Head of Office for Meta in the Pacific Northwest Region. Prior to Meta, Rajeev spent more than two decades with Microsoft, first joining as an intern in 1994. During his time there, he worked on many products, culminating in Office 365 where he built and led the team responsible for all of the Cloud Infrastructure for Office 365.Rajeev is married with two children and a spunky yellow lab named Rayna. He is very involved in and passionate about a number of efforts that uplift the local community, ranging from the arts to STEM programs. SHOW NOTES:The "Listening Tour": Grounding leadership in reality and identifying friction points (3:52)The Confluence Editor story: Reducing ship time from 120 days to 0 (6:26)Moving beyond productivity: Why "Developer Joy" is the metric that matters (8:45)Creating a community of Developer Productivity Champions and the power of a Productivity Summit (13:44)Elevating productivity to a company-level OKR and measuring qualitative sentiment (17:12)Leadership framework: Deciding when to "manage through people" vs. "manage through process" (19:05)How to give more direct ownership / responsibility to a DRI (23:03)Alignment conversations about prioritizing developer joy & productivity (24:22)Challenges faced during Atlassian’s developer joy transformation journey (26:23)How the "Developer Joy" foundation enabled building Rovo in just 6 months (30:02)The "System of Work": Expanding Jira's utility beyond engineering to finance, marketing, and legal (33:22)Rapid Fire Questions (40:48) This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/5 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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. ABOUT DANIEL LEREYADaniel Lereya has served as Chief Product and Technology Officer at monday.com since 2023. In this role, he focuses on advancing monday.com’s multi-product vision and operational efficiencies while driving execution to support company growth. Previously, he was Vice President of R&D and Product, leading global teams in shaping and executing the company’s product strategy through innovation and technology. Before joining monday.com, Daniel held leadership and engineering roles at IBM and SAP. SHOW NOTES:The three core principles of monday.com’s culture: Ownership, Transparency, and Speed of Execution (3:59)How AI acts as an accelerant to implement these cultural principles at scale (8:36)Why the “Developer” role is evolving into a “Strategic Builder” and “System Designer” (13:47)Breaking silos: How the “Builder” role blurs the lines between product, engineering, and design (17:13)Real-world example: A designer using AI to submit code and fix UI issues independently (19:09)Case Study: The “Agent Factory” & how a weekend prototype by one leader shifted the product roadmap (21:25)Operationalizing transparency: Using internal tools (“Big Brain”) to align every builder on daily business impact (25:58)The “Kickoff Meeting” framework: A strict protocol for falling in love with the problem, not the solution (32:26)The new management paradigm with AI agents as team members (37:31)Rapid fire questions (42:09) This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 and then translate that understanding back to us in human terms. ABOUT JAIME LIENJaime Lien, Ph.D. is Co-Founder and Chief Scientist at Archetype AI, a pioneering startup advancing Physical AI, artificial intelligence that understands the real world through real-time sensor data fusion.With over a dacade of experience in radar-based sensing, signal processing, and hardware engineering, Jaime’s career bridges cutting-edge research and consumer-ready innovation. Before Archetype, she led radar sensing development for Google ATAP’s Project Soli and contributed wireless communication and localization expertise at NASA’s Jet Propulsion Laboratory. ABOUT RASHI AGRAWALRashi Agrawal is Head of AI Engineering at GoodLeap, where she leads enterprise-wide AI initiatives that deliver real business impact. An accomplished speaker, she covers the latest in AI, including context engineering, evaluations, and multi-agent collaboration, while driving Applied AI innovation in the enterprise. Previously, she scaled engineering teams at Yahoo, advancing its multibillion-dollar advertising business. A passionate world traveler to 40+ countries, Rashi brings global perspective and energy to her leadership and storytelling. SHOW NOTES:Archetype AI’s mission: Building a foundation model for physical reality (0:24)The potential for discovery: Using AI to observe phenomena humans cannot perceive (1:36)Augmentation vs. Replacement: Giving humans "superpowers" rather than automating them away (2:48)The "Perfect Storm" for Physical AI: Transformers, self-supervised learning, and commodity sensors (4:04)Defining “Non-Human Intelligence” and removing the constraints of human labels (6:34)Why language is inherently lossy and insufficient for true physical understanding (8:28)Real-world application: How Physical AI aids safety decision-making in the solar industry (9:35)Use case: Improving pedestrian safety and traffic signaling in Bellevue (12:51)The biggest engineering leadership challenge: Embracing the “messiness” of real-world data (14:21)Q&A: Why we shouldn't teach AI physical laws, but let it discover them (16:50)Q&A: Validating models when there is a defined ground truth vs. subjective language (18:49)Q&A: Compute requirements and the future of active learning at the edge (20:05) LINKS AND RESOURCESVideo version of Jaime and Rashi’s session at ELC Annual 2025 This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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. ABOUT RUSLAN BELKINRuslan Belkin joined Inflection after co-founding Jelled.ai—acquired by Inflection in 2024—and previously served as CTO of Nauto. Earlier in his career, Ruslan held senior engineering roles at Twitter, LinkedIn, Netscape, and other pioneering Silicon-Valley companies, bringing more than two decades of experience at the intersection of data platforms and machine learning. SHOW NOTES:How leading engineering teams is evolving: Moving from code as the source of truth to specs/documentation as the source of truth (2:44)Why an eng org’s good hygiene / health will create better output (5:12)A framework for product vision: Envisioning the future "viscerally" like a sci-fi novel, stress-testing assumptions, and focusing smart people on the problem (9:04)Hiring in the modern era: Why software engineering is becoming "tooling and data engineering" and the importance of hiring for openness to new research (18:20)Gen Z vs. Millennial engineers: Ruslan’s observation that Gen Z is more outcome-oriented and has a lower tolerance for "corporate euphemisms." (22:24)Ruslan’s favorite frameworks for effective decision making: Using an "investment deck" to validate projects, avoid disbelief and lack of focus. (25:19)Keeping up with the velocity of change: How to curate research inputs and determine when a new paper (like DeepSeek) requires a strategic pivot. (32:57)The new burden of leadership: Why the velocity of AI requires leaders to be "right more often" and how to use models to increase research rigor. (36:27)The "Data Wall" and Synthetic Data: Why we have hit the wall for text data and how synthetic data generation loops will drive the next wave of defensibility. (41:35)The "March of 9s": Analyzing the trajectory of the AI market and why increasing agent reliability is the massive opportunity ahead. (46:25)Rapid fire questions (48:18) LINKS AND RESOURCESRuslan’s Talk at ELC Annual 2025The War of Art - Steven Pressfield’s guide to inspire and support those who struggle to express their creativity. Pressfield believes that “resistance” is the greatest enemy, and he offers many unique and helpful ways to overcome it.A Brief History of Intelligence: Evolution, AI, and the Five Breakthroughs That Made Our Brains - Artificial intelligence entrepreneur Max Bennett chronicles the five “breakthroughs” in the evolution of human intelligence and reveals what brains of the past can tell us about the AI of tomorrow. This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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! ABOUT JAMES REGGIOJames Reggio is Brex’s Chief Technology Officer. James is a forward thinking technology leader who currently oversees Brex’s entire Engineering org. James joined Brex in 2020 as Principal Engineer and has played a vital role in building the company’s mobile app and AI capabilities. Prior to Brex, James had an extensive career as a Software Engineer at leading companies such as Microsoft, Salesforce, AirBnB, Stripe and more. Additionally, James founded two companies: Altair Management and Banter, a social discovery platform for podcasts that was later acquired by Convoy in 2018. James received his B.A. of Science from The University of Texas Austin. SHOW NOTES:The birth of Brex 3.0: Using a layoff as a "moment to refound the company" (3:38)Moving from a Series E to a Series C operational mindset (5:28)The problem with a GM model: How siloed OKRs and roadmaps created "deadlock" (6:07)New rituals: Why the CEO became "chief editor of the roadmap" (8:16)The impact on morale: "Folks just knew how their work fit into the bigger picture" (11:16)The challenge of the new model: Who do you hold accountable when you "win and lose as a team"? (13:43)The lesson for reintroducing systems: "Less is more" (15:43)The "Startup within a Startup": Launching an internal team to disrupt Brex (16:49)“What if we were founding Brex again today?” The 4 constraints for the "Hacker House" experiment (17:58)Questions eng leaders should ask when running a similar experiment to Brex (21:02)Aha moment: "With agentic coating, code is so cheap" (22:35)Managing the two narratives: "compounding" the core biz vs. “innovating" with AI (26:01)A surprising dynamic: Why the AI team struggled to see their impact (while the core team didn't) (29:38)Building alongside your customer to iterate / experiment faster (36:06)The turnaround is over: Brex hits 50% YoY growth and cash-flow positive (38:45)Rapid fire questions (42:10) This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In today’s technology landscape, management as a skill is becoming more complex as teams become larger & managers must navigate the balance between relationships and strategic execution. So how can AI tools help managers level up their game? Jonathan Raymond (Founder & CEO @ Ren) shares insights that can help managers navigate their modern-day invisible cognitive loads. We cover how AI can be used to enhance – not replace – inherently human skillsets, the three components that make up an effective manager / employee relationship, product-building principles for building relational systems, and using AI to guide rather than provide concrete answers. ABOUT JONATHAN RAYMONDJonathan 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.SHOW NOTES:Jonathan’s perspective on the impossible cognitive load & colliding pressures of modern managers (2:31)The complicated workflow it takes to be a great manager (6:05)“Field Intelligence” and the need to ingest non-technical data such as (mood, sentiment, and alignment) to make better leadership decisions (9:52)The managerial matrix: high/low performers and the 10-person team that feels like 50 (12:46)The cost of mismanaging your team & why it’s so easy to get it wrong (16:02)What’s uniquely human vs. where AI provides leverage (18:01)AI’s role: detecting signal and prompting human reflection (21:04)The “Growth Loop”: a 3-part system for effective leadership (27:20)Incorporating AI tools to enhance the manager / employee relationship (31:20)The future vision: an “in-ear” AI coach that closes the gap between learning and applying (33:09)Closing the gap between learning a new skill & it becoming an unconscious habit (35:59)Product Principle: Building a “Relational System,” not just a task manager (37:49)Product Principle: Why an AI coach must ask questions, not provide answers (40:50)How to harness AI tools for better emotional articulation / processing (45:11)A simple behavioral change to try this week (47:58)Rapid fire questions (49:57)LINKS AND RESOURCESGood Authority: How to Become the Leader Your Team is Waiting For - Jonathan’s book in which he brings together what he has learned over a twenty-year journey as an executive, entrepreneur, team leader and leadership trainer.Entangled Life: How Fungi Make Our Worlds, Change Our Minds & Shape Our Futures - Merlin Sheldrake explores the spectacular and neglected world of fungi: endlessly surprising organisms that sustain nearly all living systems.Jonathan’s session at ELC Annual 2025This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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.ABOUT LAURA TACHOLaura Tacho is CTO at DX, a developer experience company. She previously led teams at companies like CloudBees, Aula Education, and Nova Credit. She’s an expert in building world-class engineering organisations that consistently deliver outstanding results. Laura has coached CTOs and other engineering leaders from startups to the Fortune 500, and also facilitates a popular course on metrics and engineering team performance.SHOW NOTES:Downsides to approaching organizational outcomes from an individual task level (2:59)Why individual product gains don’t always equate to systems-level improvements (4:56)How the quality of existing systems impacts the improvements AI can foster (7:26)Strategies for shifting mental models from the individual to systems level (9:09)Implement training & enablement techniques as an organizational lever (11:22)Common workflows that can unlock new problem-solving methods (14:46)Understanding what impact you want to see / getting the most ROI from AI (18:40)How to interpret the data when it comes to AI & its true ROI (21:22)AI data literacy for engineering leaders (23:06)Interpreting the meter study & what it means for engineers using AI (25:49)Quality vs. quantity when it comes to AI implementation on the org level (28:43)Characteristics that high-ROI companies possess when it comes to AI (30:35)Strategies to invest in that may lead to higher ROI (32:29)Laura’s observations on time & money budgeting / investments for 2026 (35:28)Embracing cost savings & opportunity generation as an eng org (38:08)Tackling fear / uncertainty when it comes to AI adoption, budgeting, & ROI (40:01)LINKS AND RESOURCESPrevious Episode with Laura TachoIntroducing the AI Measurement Framework from DXAtlassian State of DevEx ReportMETR StudyDORA Report (2025)This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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.ABOUT MIRIAM AGUIRREMiriam Aguirre is the Co-Founder and CEO of Ingenimax, the company behind StarOps, an AI-powered platform engineering engine that helps teams deploy and manage kubernetes and other cloud-native systems in minutes, not months. Before Ingenimax, Miriam served as CTO and engineering leader at two startups that successfully scaled from early stage through IPO. Her career spans deep expertise in high-throughput, scalable systems and machine learning, with a focus on building the technical and organizational foundations for hypergrowth. Miriam is passionate about engineering leadership that turns complex technology into intuitive, reliable platforms, and about helping teams scale without losing their soul. ToolHive Unlocks the Full Value of MCP & Your AI AgentsSo you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.Leaders trust ToolHive to put MCP into production and put their AI agents to work.ToolHive is open source, so get started for free at toolhive.dev SHOW NOTES:The Origin Story of Ingenimax (3:05)The recurring scaling problem: Why "scaling teams" means scaling systems first (5:23)How the age of AI forces platform strategy to evolve earlier in a company’s journey (8:48)The decline of vendor lock-in and the rising appetite for experimentation with tech (10:56)The paradigm shift that breaks the old model: natural language as the new interface (14:11)Why deep knowledge of fundamentals is now more important than syntax (16:56)Shifting requirements conversations from tactical inputs to strategic outcomes (20:22)Balancing standardization and flexibility with guardrails in an AI-driven environment (22:58)The challenge of getting from an AI prototype to a polished product (26:42)How platform team roles will evolve to focus more on curation (29:32)How to become a great technology curator (37:30)Rapid Fire Questions (39:56)LINKS AND RESOURCESThe Book of George - From the author of the critically acclaimed Laura & Emma comes a The Love Affairs of Nathaniel P. for our times: Kate Greathead's razor-sharp but big-hearted excavation of millennial masculinity.Can Animals and Machines Be Persons?: A Dialogue - This is a dialogue about the notion of a person, of an entity that thinks and feels and acts, that counts and is accountable. Equivalently, it's about the intentional idiom --the well-knit fabric of terms that we use to characterize persons. Human beings are usually persons (a brain-dead human might be considered a human but not a person). However, there may be persons, in various senses, that are not human beings. Much recent discussion has focused on hypothetical computer-robots and on actual nonhuman great apes. The discussion here is naturalistic, which is to say that count and accountability are, at least initially, presumed to be naturally well-knit with the possession of a cognitive and affective life.This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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! ABOUT CHRYSTAL HENKE BALLChrystal Henke Ball a seasoned engineering leader, currently serving as VP of Engineering at Yahoo, where she leverages her experience to accelerate product development across core products such as Yahoo.com and the Yahoo News app. Prior to Yahoo, she led engineering organizations at Google Search, Pandora, Pachama, and Arcadis, building highly available systems, guiding architectural transitions, spearheading novel solutions, and delivering delightful user experiences. Chrystal excels at designing purpose-driven, scalable architectures, streamlining development processes, and mentoring teams to work effectively and openly together. ToolHive Unlocks the Full Value of MCP & Your AI AgentsSo you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.Leaders trust ToolHive to put MCP into production and put their AI agents to work.ToolHive is open source, so get started for free at toolhive.dev SHOW NOTES:Navigating the challenge of balancing constraint vs. innovation (3:05)Considerations for balancing current capabilities w/ your roadmap to change (4:34)Frameworks for categorizing what’s fixed vs. in flux to aid decision-making (6:14)Conversation points for checking your assumptions (7:36)The new leadership challenge: vision as a bottleneck (14:45)Evolving feedback loops to address a more fluid product lifecycle (19:43)Defining product vision in today’s fast-paced, fluid landscape (23:57)Defining grit as an essential trait & ways to cultivate it as an eng leader (31:57)Building AI-incorporated products with trust as a foundational principle (40:46)Rapid fire questions (43:01) LINKS AND RESOURCESTalking to Strangers: What We Should Know About the People We Don't Know - Malcolm Gladwell, host of the podcast Revisionist History and author of the #1 New York Times bestseller Outliers, offers a powerful examination of our interactions with strangers -- and why they often go wrong.Terrestrials - A show for people of all ages that explores the strangeness that exists right here on Earth. In each episode, host Lulu Miller (co-host of Radiolab) will introduce you to a creature or earthly phenomenon that will defy your expectations of how nature is supposed to work. Along the way, you'll encounter a chorus of experts, including scientists, surfers, hip hop artists and…a "Songbud" named Alan (indie punk musician Alan Goffinski) who creates original songs for key moments of confusion, discovery or awe. New episodes drop Thursdays. Listen in with your whole family. Or all alone. This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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.ABOUT SIMONE KALMAKISSimone Kalmakis is the VP of Engineering at Viam, a platform unlocking AI, data, and automation for devices in the physical world. She has deep experience applying AI and machine learning to big data and big missions, and is known for building healthy engineering organizations that drive business value and real-world progress.Prior to Viam, Simone was Senior Director of Engineering at Arcadia, a climate tech company building an API platform for residential utility data to power solutions that fight climate change. Before that, she served as Director of Engineering at Flatiron Health, where she helped accelerate the development of cancer treatments through real-world data.Simone began her career at Microsoft, developing machine-learned relevance algorithms for Bing. She’s also a successful founder––after Microsoft, she built and sold Symbi, a roommate-matching startup. She holds a degree in Mathematics and Economics from Yale University. ToolHive Unlocks the Full Value of MCP & Your AI AgentsSo you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.Leaders trust ToolHive to put MCP into production and put their AI agents to work.ToolHive is open source, so get started for free at toolhive.dev Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. 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!🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES:Simone’s eng leadership journey from health-tech to climate to robotics (3:25)Lessons from being a founder & how it led to Viam (5:27)Co-founding lessons that Simone continues to apply (7:22)Navigating the transition from Flatiron Health to Arcadia (9:20)Transitioning from Arcadia to Viam (12:06)Use cases of physical devices impacting the environment through data / AI (14:28)How Simone sees Viam potentially working in a day-to-day capacity (15:42)How to structure your time when entering a new industry (17:51)Onboarding with a personal project to build user empathy, alignment & motivation (20:34)Finding where your expertise is the highest-leverage for your org (22:34)“The goal is not to maintain the same level of depth in each of your teams” (24:18)How to decide which teams get your deep focus (27:15)Building trust through transparent communication about your priorities (29:19)The lifecycle of a leadership “deep dive” from start to exit (32:20)Advice for leaders adopting this hands-on, flexible approach (36:15)Key questions to ask when seeking a more mission-aligned industry (38:01)Rapid fire questions (40:33)LINKS AND RESOURCESViam - a full-stack solution for the kinds of devices that exist anywhere from your home, your office, in cars or boats, in warehouses or factories, at arenas, or other public places.This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

"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. ABOUT BEN KUSBen Kus is the Chief Technology Officer at Box, where he leads technology and AI strategy to help enterprises securely unlock insights from their unstructured data. Ben’s career spans engineering, product leadership, and startup innovation—including co-founding Subspace (acquired by Box) and being an early employee at BigFix (acquired by IBM), where he later served as Chief Architect of Mobile Security. Ben holds a degree in Computer Science from UC Berkeley. ToolHive Unlocks the Full Value of MCP & Your AI AgentsSo you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.Leaders trust ToolHive to put MCP into production and put their AI agents to work.ToolHive is open source, so get started for free at toolhive.dev Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. 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!🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES:How Generative AI sparked Box’s reoriented vision, by unlocking the value of unstructured data (3:29)Using GenAI to create structure out of unstructured data (5:28)Internal & external conversations that inspired Box’s new direction (7:18)Box’s “platform first” approach to building a secure and scalable foundation for all future AI features (10:02)Why security and compliance must be built in from "day negative one" not added on later (12:40)How to set a technical vision that can respond to future developments you can't yet predict (14:46)The “multi-speed” business model: Using a small, fast-moving internal group to test ideas before they enter the normal, slower development cycle (17:47)Example of a successful project: AI-driven data extraction & the evolution to critical feature (20:26)The story of an abandoned project and the challenge of knowing which ideas are revolutionary versus which aren’t worth continuing (22:17)Ben’s long-term vision for AI agents and why he believes they are an incredibly powerful technology paradigm (23:58)State diagrams & the journey behind building Box’s initial agentic AI systems (26:50)“Context Engineering”: The new paradigm of programming and the mental model shift required for engineers to adopt it (29:07)The future of AI benchmarks: Measuring what a person can accomplish with an agent, not just the agent’s performance alone (31:03)How to balance development speed with security risks, especially when agents can take actions and change the environment (34:00)Key questions to ask to determine the right guardrails for AI agents, including thinking about the worst-case scenario (36:41)Enterprise technology trends to watch, and why multi-agent systems will become the new “org chart” (37:56)Rapid fire questions (39:03)LINKS AND RESOURCESHarry Potter and the Methods of Rationality - Eliezer Yudkowsky’s alternate-universe Harry Potter fan-fiction wherein Petunia Evans has married an Oxford biochemistry professor and young genius Harry grows up fascinated by science and science fiction. When he finds out that he is a wizard, he tries to apply scientific principles to his study of magic, with sometimes surprising results.This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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.To learn more & get tickets, go to sfelc.com/annual2025Use code podcast15 for 15% off tickets - group tickets / discounts available. ABOUT ELC ANNUALThe playbook for engineering leadership is being rewritten. ELC Annual 2025, happening September 10-11 in San Francisco, is where you'll gain the insights, strategies, and deep connections needed to lead in this new era. 50+ speakers, 50+ peer-led roundtables discussions, 1:1 matching to expand your network. Insights, connections & support.Join the community of engineering leaders who are co-creating the future of our field.Listener Discount → Use code podcast15 for 15% offGroup Tix → For teams looking to attend together, special group discounts can be found under the 'Tickets' section of our website!Secure your ticket at sfelc.com/annual2025 ToolHive Unlocks the Full Value of MCP & Your AI AgentsSo you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.Leaders trust ToolHive to put MCP into production and put their AI agents to work.ToolHive is open source, so get started for free at toolhive.dev Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. 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!🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES:The ground is shifting: Why the old playbooks for engineering leaders are being rewritten (0:55)Moving beyond AI hype to harnessing its real power in your products and workflows (2:44)How are teams & workflows changing? Redefining roles and upskilling your team for the AI era (9:06)Why the smartest insights don't come from the stage, but from deep, honest conversations with peers in roundtables (13:36)How curated one-on-one matches help you build a trusted network to rely on for years to come (16:08)ELC Annual isn't a tech conference; it's a career conference to invest in yourself and your leaders (17:49) This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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.ABOUT MICHAEL GRINICHMichael is the founder and CEO of WorkOS, a developer platform that enables companies to become Enterprise Ready through features like Single Sign-On (SAML). Their customers include many of the fastest-growing startups including Webflow, Drata, Loom, and +200 others. Before WorkOS, Michael co-founded Nylas and studied CS at MIT. ToolHive Unlocks the Full Value of MCP & Your AI AgentsSo you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.Leaders trust ToolHive to put MCP into production and put their AI agents to work.ToolHive is open source, so get started for free at toolhive.dev Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. 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!🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES:Marketing technical products exclusively to other tech companies (2:39)Building products end-to-end without PMs (6:36)How WorkOS utilizes fun, user feedback, and cohesive storytelling in their product-building process (9:31)Hiring engineers for curiosity & comfort operating in ambiguity (12:48)How engineers owning product discovery & directly engaging w/ users improve product insights (16:31)Using Slack for real-time integrated support & rapid product iteration (19:38)The complexities of creating simple, elegant products and marketing messaging (21:54)Cut scope ruthlessly to ship faster and better (26:20)Small, simple, deeply useful features make the biggest impact (30:30)The weekly cadence that keeps engineering aligned (32:52)Behind the scenes of MCP Night: A protocol party for devs (38:20)Rapid fire questions (41:29)LINKS AND RESOURCESMCP Night**WorkOS Launch Week**WorkOS AuthKitThe Business Value of Computers: An Executive's Guide - Paul A. Strassmann addresses the practical needs of executives responsible for planning, budgeting and justifying information technology expenditures. It shows that there is no direct relation between spending on computers, profits or productivity.This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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.ABOUT SRINATH KURUVADISrinath Kuruvadi is a globally recognized cybersecurity executive and cloud security leader with over two decades of experience driving security innovation at some of the world’s most influential technology companies, including Netflix, Meta, Google, Lyft, and JPMorgan Chase. Currently serving as Managing Director and Head of Cloud Security at JPMorgan Chase, he leads the enterprise-wide security strategy across APIs, containers, and cloud platforms, shaping the future of banking technology.Srinath’s approach blends deep technical expertise with executive-level risk management. At Netflix, he headed cloud security for one of the largest AWS environments globally, pioneering scalable governance and identity systems that supported massive data throughput. At Meta and Google, he led the development of custom infrastructure security systems protecting billions of users, including Facebook’s Blackbird SIEM+SOAR platform.Beyond his executive roles, Srinath is a strategic advisor and angel investor, with five successful startup exits including Bridgecrew, Lightspin, Oxeye, Gem Security, and Kivera. He is also a trusted advisor to venture capital firms like YL Ventures and Glilot Capital Partners, and served on Amazon’s Global CISO Advisory Council.He holds multiple patents in web application security, database protection, and abuse detection, and has authored research on algorithmic solutions in industrial systems. Srinath is also multilingual and committed to lifelong learning, exemplified by a sabbatical that took him to over 35 countries for cultural, linguistic, and creative growth.With a Master’s degree in Computer Science from North Carolina State University and a Bachelor's from BITS Pilani, Srinath is known for transforming security from a blocker into a business accelerator.Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. 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!🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES:The hidden art of influencing without authority in security leadership (3:29)Why influencing remains an underestimated skill (5:08)Shifting from accidental to intentional influencing (6:53)Frameworks for aligning problems from other stakeholder’s POV (8:40)How to effectively influence without formal authority (11:14)Common pitfalls in identifying & aligning shared outcomes - and how to avoid them (14:10)Srinath’s strategy for clearly defining and aligning on shared outcomes from the start (15:42)Making a compelling case when immediate ROI isn’t clear (17:47)Practical prioritization frameworks for assessing security needs (20:55)Insights on personal time management for engineering leaders (22:53)Navigating current trends and potential pitfalls in AI for security (26:29)Inside the Innovation Lab: Operationalizing curiosity and AI experimentation (29:57)Rapid fire questions (33:47)LINKS AND RESOURCESFAIR methodology risk assessment - a research-driven not-for-profit organization dedicated to advancing the discipline of cyber and operational risk management through education, standards and collaboration.The First 90 Days: Critical Success Strategies for New Leaders at All Levels - Michael D. Watkins gives you the keys to successfully negotiating your next move—whether you’re onboarding into a new company, being promoted internally, or embarking on an international assignment.Range: Why Generalists Triumph in a Specialized World - David Epstein’s compelling case for actively cultivating inefficiency. Failing a test is the best way to learn. Frequent quitters end up with the most fulfilling careers. The most impactful inventors cross domains rather than deepening their knowledge in a single area. As experts silo themselves further while computers master more of the skills once reserved for highly focused humans, people who think broadly and embrace diverse experiences and perspectives will increasingly thrive.Influence: The Psychology of Persuasion - Dr. Robert Cialdini explains the psychology of why people say "yes"—and how to apply these understandings. You'll learn the six universal principles, how to use them to become a skilled persuader—and how to defend yourself against them. Perfect for people in all walks of life, the principles of Influence will move you toward profound personal change and act as a driving force for your success.How to Win Friends & Influence People - Dale Carnegie’s timeless bestseller, packed with rock-solid advice that has carried thousands of now famous people up the ladder of success in their business and personal lives.This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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.ABOUT JOHN AMARALJohn Amaral, CTO and co-founder of Root.io, is a veteran cybersecurity leader with a proven track record of scaling and exiting successful companies. At Cisco, he led Product for Cloud Security—its fastest-growing Security and SaaS business. Before that, he ran product and engineering at CloudLock through its acquisition by Cisco in 2016. Earlier, as SVP of Product at Trustwave, John led its industry-leading security portfolio, culminating in a strategic acquisition by Singtel. Today, he’s building Root.io—a next-gen cybersecurity platform pioneering Agentic Vulnerability Remediation (AVR) to automate and eliminate software vulnerabilities at scale. Join us at ELC Annual 2025ELC Annual is the premier event for engineering leaders. 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!🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES:The evolving role of engineering leaders (2:13)“Shift Left is Dead” - Why it’s time to “Shift Out” (5:59)Applying Jobs-To-Be-Done & offloading toil with AI (11:00)Root.io’s AI-driven approach to security (15:03)Vision First Leadership (22:36)Empowering developers & shipping daily (27:38)Rethinking product & engineering orgs and building your vision muscle (30:47)Unlocking creativity through hobbies (36:37)Rapid fire questions (41:14)LINKS AND RESOURCESThe All-In Podcast - When the pandemic prevented four friends from convening their weekly poker game, they took to the airwaves to socialize and discuss the news of the day. What started on a whim has quickly become one of the top-ranked podcasts in the world.This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.