Explore every episode of the podcast The Engineering Leadership Podcast
| Title | Pub. Date | Duration | |
|---|---|---|---|
| Developing the modern builder framework and managing the cross-pollination of roles at scale w/ Pratima Arora #274 | 27 oct. 2026 | 00:38:58 | |
In this episode, Pratima Arora, Chief Product and Technology Officer @ Smartsheet, dives into what it means to be a modern builder as product, design, and engineering roles converge into today’s post-AI world. She and Jerry discuss why the modern builder model is disrupting traditional engineering processes / responsibilities as individuals embrace a breadth of skills while maintaining individual expertise. They cover how to encourage “cross-pollination” of roles, maintaining product quality while improving iteration speed, facilitating bottom-up contributions, creating context / knowledge graphs to inform agents, examples of good product builders, and what this means for hiring. ABOUT PRATIMA ARORA Pratima Arora is the Chief Product and Technology Officer at Smartsheet. In this position, she is responsible for the company’s product management, product marketing, user experience, pricing and packaging, and digital and product partnerships. An accomplished technology executive, Pratima has more than 20 years of experience as a product and technology leader with a passion for building innovative tools that solve real problems. She has held senior product leadership roles at Atlassian and Salesforce, working on some of the companies’ highest-revenue products. Most recently, she was Chief Product and Technology Officer at Chainalysis, where she led the global R&D organization for one of the world’s top blockchain data platforms. She holds a B.S. in Physics, an M.S. in Computer Science, and an MBA from UC Berkeley’s Haas School of Business. The CAFE(S) framework is a research-backed definition of context quality for AI agents. DX collaborated with researchers at Capital One, Google, and UVic to give teams a shared standard for reviewing agent context by breaking it into five properties: clarity, actionability, fidelity, efficiency, and security. Your agent is only as good as its context and the CAFE(S) framework establishes a shared language around context to help you better understand how & why agents go wrong. Check it out here!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Jerry Li - Host Noah 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. | |||
| Best practices for scaling AI adoption across a large org & the trade offs you will have to make w/ Sagnik Nandy #273 | 20 oct. 2026 | 00:42:15 | |
In this episode, Sagnik Nandy (CTO & EVP of Engineering @ Docusign) joins Jerry to discuss keys to success when it comes to peer-led AI transformation. Sagnik shares how they approached AI adoption internally @ Docusign with the use of both champions & multipliers, understanding trade offs associated with AI adoption, determining which tasks to assign to agents, frameworks for measuring the ROI of agentic tools, and how it helps bring value to your customers. He also discusses how to measure the customer productivity index (CPI) and what it takes to mitigate customer issues when scaling AI internally. ABOUT SAGNIK NANDY Sagnik Nandy is the Chief Technology Officer and Executive Vice President of Engineering at Docusign responsible for engineering, cloud operations, and technology strategy that enables customers globally to run their organizations on Docusign. Most recently, Sagnik served as the President and Chief Development Officer for Workforce Identity at Okta where led engineering development and operations, product management, and design and user research. Earlier, he joined Okta as their CTO, overseeing the engineering and business technology arms of the company. Prior to Okta, Sagnik served as the Vice President of Engineering at Google where he oversaw several critical components of Google’s core advertising business, the backbone of the company’s growth and revenue. During his 15 years at Google, Sagnik also helped build Google’s Measurement and Analytics offerings and took several products from inception to becoming market leaders. Sagnik has a bachelor’s degree from the BITS, Pilani (Birla Institute of Technology and Science Pilani) and a Ph.D. in computer science and engineering from UC San Diego. The CAFE(S) framework is a research-backed definition of context quality for AI agents. DX collaborated with researchers at Capital One, Google, and UVic to give teams a shared standard for reviewing agent context by breaking it into five properties: clarity, actionability, fidelity, efficiency, and security. Your agent is only as good as its context and the CAFE(S) framework establishes a shared language around context to help you better understand how & why agents go wrong. Check it out here!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Building your support network, picking the right projects, and why eng leaders make good investors w/ Amit Gupta #272 | 13 oct. 2026 | 00:43:21 | |
Amit Gupta, Partner @ SNR Ventures, joins Jerry to discuss his unique eng leadership journey and how that led him to his second career as an investor / coach. We cover some of the lessons learned throughout his time working as VP of various startups and how those experiences shaped his desire to start his own consulting business. Amit defines what a coaching tree is and his philosophy when it comes to mentorship, picking the right projects, and determining what a team needs to work effectively together. Throughout the conversation, we revisit why effective engineering coaching also includes mentorship around company building. Lastly, Amit discusses why eng leaders make good investors and how investing was a natural continuation off of engineering for him. ABOUT AMIT GUPTA Amit Gupta has held leadership roles at multiple high-growth companies from early-stage through the public markets, including Qualcomm, INQ Mobile, Lookout, and Benchling. He combines concentrated, early stage investing with a passion for helping technical founders with company building. In some cases that materializes into a role helping in the trenches and in others a more passive, help as needed voice. Amit has helped countless companies directly and as an advisor to Y Combinator Continuity. The CAFE(S) framework is a research-backed definition of context quality for AI agents. DX collaborated with researchers at Capital One, Google, and UVic to give teams a shared standard for reviewing agent context by breaking it into five properties: clarity, actionability, fidelity, efficiency, and security. Your agent is only as good as its context and the CAFE(S) framework establishes a shared language around context to help you better understand how & why agents go wrong. Check it out here!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Building software factories and making the transition from a pre-AI to post-AI world as a large company w/ Zohar Einy #271 | 06 oct. 2026 | 00:38:17 | |
Zohar Einy, CEO & Co-Founder @ Port, shares best practices for building a software factory, how software factories impact the organizational structure of your org, and scaling strategies. He and Jerry discuss why software factories can contribute to a significant ROI, tools for helping your teams navigate the transition from building a product for agents vs. people, and what scary (but healthy) decision-making looks like as an eng leader in a post-AI world. Zohar also shares some of his core beliefs when it comes to developing talent & hiring young engineers @ Port. ABOUT ZOHAR EINYZohar Einy is the co-founder and CEO of Port, the agentic SDLC platform helping companies like GitHub, Visa, and PwC build and scale their AI Software Factories. Port has raised $158M, backed by General Atlantic, Accel, Bessemer Venture Partners, Team8, and TLV Partners. The idea for Port began during Zohar and co-founder Yonatan Boguslavski’s time as engineers in the IDF’s Unit 8200, where they built a platform to help developers move more quickly at scale. After recognizing the same challenge across the broader market, they founded Port in 2022. The CAFE(S) framework is a research-backed definition of context quality for AI agents. DX collaborated with researchers at Capital One, Google, and UVic to give teams a shared standard for reviewing agent context by breaking it into five properties: clarity, actionability, fidelity, efficiency, and security. Your agent is only as good as its context and the CAFE(S) framework establishes a shared language around context to help you better understand how & why agents go wrong. Check it out here!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Utilizing AI to assist in EPD and non-EPD functions & how curiosity can drive organizational change w/ Ali Dasdan #270 | 29 sept. 2026 | 00:43:43 | |
Ali Dasdan, CTO @ Dropbox, joins the pod to share insights on the company’s large-scale AI adoption and research as a foundation of successful engineering leadership. First, Ali shares insights on why he continues publishing research despite his role as a CTO and how research / curiosity can drive better trust within your organization. He shares about how his research ultimately guided decision making regarding redrawing Dropbox’s entire architecture and the importance of creating a record of the company’s progression as the rearchitecture occurred. The bulk of the conversation centers around how Dropbox is adopting AI, including tools like Nova and Dash, within both EPD and non-EPD departments. ABOUT ALI DASDAN Ali Dasdan is a C-suite technology executive with 25+ years building, scaling, and leading global engineering, product, and technical-operations organizations of up to ~1,000 people across a dozen industries, in public companies, high-growth startups, and enterprises in Silicon Valley and London. Today he is CTO of Dropbox, serving over 700 millions of users on an exabyte-scale platform with $2.5B+ revenue, where he also leads the AI strategy and AI enablement. Previously EVP and CTO of ZoomInfo and VP of Engineering at Atlassian (Confluence Cloud, Trello, Jira Work Management). As CTO (at Turn, Vida, Poynt, ZoomInfo, and Dropbox) he defines and owns company-wide technology strategy; in divisional roles (eBay, Atlassian, Tesco, Yahoo) he led engineering for revenue-critical parts of the business. SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Implementing scalable and powerful agentic tools across your organization w/ Ozzie Osman #269 | 23 sept. 2026 | 00:46:04 | |
In this episode, Jerry discusses key insights on delegating to agentic tools while maintaining high levels of engineering ownership with Ozzie Osman, co-founder @ Monarch. Ozzie shares what it looks to pursue two paths when it comes to AI: agentic-forward and human-orchestrated pipelines. They also cover the specific AI tools that are used in Monarch, including Devin and Voltron; assigning tasks to be AI-first vs. human-led; determining which pieces of customer feedback lead to new features; and common challenges when it comes to AI-generated code and what the human review process for it looks like. ABOUT OZZIE OSMAN Osman (Ozzie) Osman is co-founder of Monarch. He is the lead author of the Holloway Guide to Technical Recruiting and Hiring. He has built products and engineering teams at companies including Quora and Google. Ozzie has also started two companies that have been acquired, and advised dozens of other startups. Sinch is the communications infrastructure the AI era runs on. There's a layer of infrastructure behind every text, call, and login code your product sends, and it works exactly like plumbing: nobody thinks about it until it's the reason something broke. Most providers route through 4-6 intermediaries; Sinch connects in 1-2 hops, direct carrier relationships across 600+ connections, handling 900 billion interactions a year across 60+ countries. Routing, compliance, fraud prevention handled automatically rather than manually managed by the business sending the message! Sinch is the reliability layer underneath AI-driven customer communications; the infrastructure that determines whether an AI agent's output actually reaches a real person as a delivered text, connected call, or verified interaction. Check it out here!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Navigating from individual AI adoption to team-level transformation while scaling w/ Jakub Oleksy #268 | 17 sept. 2026 | 00:50:38 | |
Jakub Oleksy, SVP of Software Engineering @ Github, joins the podcast to discuss how Github is addressing some of the biggest challenges facing the industry when it comes to infrastructure scaling, customer capacity, and using AI to add value to your org’s processes and eng leaders’ decision-making. He shares how scaling looked different at Github six years vs. today, how they navigated the migration to Azure, and what AI transformation looks like individually & at the team level. Jakub also discusses insights for eng leaders when it comes to investing in yourself & your people and making cross-functional decisions. Sinch is the communications infrastructure the AI era runs on. There's a layer of infrastructure behind every text, call, and login code your product sends, and it works exactly like plumbing: nobody thinks about it until it's the reason something broke. Most providers route through 4-6 intermediaries; Sinch connects in 1-2 hops, direct carrier relationships across 600+ connections, handling 900 billion interactions a year across 60+ countries. Routing, compliance, fraud prevention handled automatically rather than manually managed by the business sending the message! Sinch is the reliability layer underneath AI-driven customer communications; the infrastructure that determines whether an AI agent's output actually reaches a real person as a delivered text, connected call, or verified interaction. Check it out here!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Hiring top-tier talent, leveraging open source models, and staying competitive in the age of AI w/ Benny Chen #267 | 02 sept. 2026 | 00:35:01 | |
Benny Chen, Co-Founder @ Fireworks AI, joins the show to discuss his founder journey and share valuable insights on navigating common founder / product dev challenges in today’s agent-first landscape. He and Jerry cover strategies for creating effective messaging, staying competitive in a crowded market space, hiring top-tier talent / what qualities to look for in high-performing engineers, navigating the cultural shift to managing agents, creating data flywheels & how this can help your customers, and more. ABOUT BENNY CHEN As co-founder and early product architect, Benny Chen shaped Fireworks AI’s infrastructure strategy, spearheading the design of scalable systems to support high-throughput AI model serving. Benny’s contributions established the technical foundation for Fireworks AI’s robust and cloud-native architecture, which underpins its ability to meet enterprise demands. Formerly Meta’s Ads Infrastructure Lead, Benny optimized large-scale ad-serving pipelines and developed significant expertise in distributed systems and cloud infrastructure. He holds a B.S. in Computer Science from Stanford University, bringing both leadership and technical depth to the Fireworks AI management team. Sinch is the communications infrastructure the AI era runs on. There's a layer of infrastructure behind every text, call, and login code your product sends, and it works exactly like plumbing: nobody thinks about it until it's the reason something broke. Most providers route through 4-6 intermediaries; Sinch connects in 1-2 hops, direct carrier relationships across 600+ connections, handling 900 billion interactions a year across 60+ countries. Routing, compliance, fraud prevention handled automatically rather than manually managed by the business sending the message! Sinch is the reliability layer underneath AI-driven customer communications; the infrastructure that determines whether an AI agent's output actually reaches a real person as a delivered text, connected call, or verified interaction. Check it out here!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Applying Agentic AI to the Supply Chain, Building Systems to Withstand Chaos, and Leveraging your Curiosity w/ Pooja Brown #266 | 25 août 2026 | 00:54:24 | |
In this episode, Pooja Brown (Founder @ Inventry.ai) shares her insights on balancing being a founder & technologist, especially within the mid-market manufacturing industry. We cover why founders need to lead with curiosity as they seek out customer problems to solve, strategies for solving complex problems related to supply chain, and strategies for selling your products. Pooja also dissects important fundraising tactics, how to identify areas that AI tooling can enhance within your business, reading customer signals, and bolstering your engineering skills by leveling up business capabilities. ABOUT POOJA BROWN Pooja Brown is a technology executive and founder focused on building AI-native platforms that power real-world operations across industries. She has led engineering at scale at companies like Stitch Fix and DocuSign, building systems that combine data, workflows, and machine learning to drive everything from personalization and supply chain to digital agreements used by hundreds of thousands of businesses.Her experience spans multiple verticals including retail, enterprise SaaS, education technology, and real estate, where she has consistently focused on embedding AI directly into core business systems rather than layering it on top. Pooja is currently the founder and CEO of Inventry.ai, where she is building autonomous AI agents that help mid-market manufacturers run procurement and supply chain operations more effectively. Across her career, she has focused on turning complex operational data into systems that don’t just generate insights, but actually drive decisions and execution. Sinch is the communications infrastructure the AI era runs on. There's a layer of infrastructure behind every text, call, and login code your product sends, and it works exactly like plumbing: nobody thinks about it until it's the reason something broke. Most providers route through 4-6 intermediaries; Sinch connects in 1-2 hops, direct carrier relationships across 600+ connections, handling 900 billion interactions a year across 60+ countries. Routing, compliance, fraud prevention handled automatically rather than manually managed by the business sending the message! Sinch is the reliability layer underneath AI-driven customer communications; the infrastructure that determines whether an AI agent's output actually reaches a real person as a delivered text, connected call, or verified interaction. Check it out here!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Hiring top-tier talent, the importance of adopting an evolutionary mindset, and taking critical feedback to solve technical problems w/ Sergiy Nesterenko #265 | 04 août 2026 | 00:49:29 | |
In this episode, Sergiy Nesterenko (CEO @ Quilter) joins the pod to share how he turned a personal technical challenge into his own company, even before the market caught up. He shares his unique journey from SpaceX to Quilter and addresses common eng leader / founder challenges, including taking critical feedback to solve tough technical problems, knowing when your most important role is educating the market / customers, and choosing the right customers. Sergiy and Jerry also dissect insights into principles around building circuit boards, and common misconceptions around hiring top-tier talent, finding investors, and procuring customers as an early-stage company. ABOUTSERGIY NESTERENKO Sergiy Nesterenko is the Founder and CEO of Quilter, the first physics-driven AI platform that fully automates PCB layout design. Under his leadership, Quilter has pioneered autonomous board design – creating the missing automation layer for hardware and compressing weeks-long layout cycles into hours. Backed by Index, Benchmark, Coatue, and Tony Fadell, Quilter is redefining what's possible in hardware development. Previously, Sergiy spent five years at SpaceX as a Senior Radiation Effects Engineer, building electronics for the Falcon 9 and Falcon Heavy. SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Determining bets, using customer insights to pivot, and gaining developer buy-in & trust w/ Tomas Reimers #264 | 21 juil. 2026 | 00:38:01 | |
Tomas Reimers, Co-Founder & CPO @ Graphite, reveals his journey to becoming a founder and some of the major moments from Graphite’s product development story. He dissects frameworks for determining when it’s time to quit your full-time job to pursue becoming a founder and analyzing the costs vs. benefits of that decision. We cover how to decide what customer problems to solve, understanding how software development trends impact what you’re building, and product market fit and selling considerations. Lastly, Tomas shares valuable strategies when it comes to selling to developers. ABOUT TOMAS REIMERS Tomas Reimers is the CPO and co-founder of Graphite, the a16z and Anthropic-backed AI code review platform that Cursor acquired in December 2025. Previously, he was an engineer at Facebook. Passionate about advancing developer velocity, Tomas holds a BS in Computer Science from Harvard University. SHOW NOTES:
LINKS AND RESOURCES
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Utilizing AI internally to iterate faster and empower smaller teams to upskill w/ Vivek Raghunathan #263 | 07 juil. 2026 | 00:37:47 | |
Vivek Raghunathan, SVP of Engineering @ Snowflake, joins the Engineering Leadership Community Podcast to discuss all things AI – most importantly, how Snowflake is utilizing AI internally to iterate faster with smaller, focused teams. Vivek shares how AI and lower coding costs ultimately help Snowflake implement tighter feedback loops between customer & eng teams to speed up product development rollout and how Snowflake empowers their orgs to upskill when it comes to AI. Jerry & Vivek also break down what quality leadership looks like across the board and the role of AI in shaping today’s eng leaders. ABOUT VIVEK RAGHUNATHAN Vivek Raghunathan is Snowflake's SVP of Engineering. Before joining Snowflake, Vivek co-founded Neeva, one of the first AI-native search engines for consumers, which was acquired by Snowflake in 2023. Prior to that, he spent more than a decade at Google, where he led YouTube monetization and helped launch Google Now. ABOUT SNOWFLAKE Snowflake is the data and AI platform that many of the world's largest organizations rely on to power their most critical operations. Whether a bank is approving a loan, a retailer is optimizing its supply chain, or a hospital is bringing together patient data, Snowflake helps organizations unify data, apply AI, and make faster, more informed decisions. Today, over 13,900 companies rely on Snowflake to turn their data into business value, with enterprise-grade security, governance, and scale built-in. SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| The Product Paradigm Shift: How Livekit Navigated High Stakes Scaling Challenges to Build the Future of Voice-First AI Interfaces w/ Russ d’Sa #262 | 23 juin 2026 | 00:46:13 | |
Russ d’Sa (CEO & Co-founder @ LiveKit) joins the show to deconstruct the "Product Paradigm Shift" toward voice-driven interfaces and agent-centric UX . We dive into LiveKit’s high-stakes scaling lessons: from powering OpenAI and Character AI’s voice mode, how they navigated real time bottlenecks to hit the next level of scale, the architectural necessity of a multi-cloud strategy, and the foundations of a co-founder relationships that can effectively blend engineering & business strategy. ABOUT RUSS D’SA Russ is a startup vet who founded his first company in the 2007 YC batch and was the 2nd frontend engineer hired at Twitter, Russ d'Sa now leads voice AI unicorn LiveKit. They're the backbone of ChatGPT Voice Mode, Salesforce Agentforce, Grok, and roughly 30% of US 911 calls. ABOUT LIVEKIT LiveKit is an open source framework and cloud platform for building voice, video, and physical AI agents. It provides the tools you need to build agents that interact with users in realtime over audio, video, and data streams. Agents run on the LiveKit server, which supplies the low-latency infrastructure (including transport, routing, synchronization, and session management) built on a production-grade WebRTC stack. This architecture enables reliable and performant agent workloads. SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Building an empowered career w/ Jean Hsu & Cate Huston #261 | 10 juin 2026 | 00:47:47 | |
In this episode, Patrick discusses what it means to build an empowered career & explore creative career portfolios with Jean Hsu (VP of Engineering @ Range) and Cate Huston (author of The Engineering Leader and fractional CTO @ Twill). Both share their unique engineering leadership journeys & how they built creative career paths through exploration & finding room for optionality. We dissect the identity crisis that eng leaders face – whether they are ICs or managers – and how to navigate the tension between individual & team productivity, especially taking into consideration AI. Lastly, Jean and Cate share insights on letting go of societal norms, unique ways to expand your work, taking on bets, and incorporating your values into your career. ABOUT JEAN HSU Jean is a builder, writer, coach, and fractional VPE at Circuit & Chisel. She was previously in leadership roles at Pulse, Medium, and Range, and also built out a leadership development company focused on engineers. She lives in Berkeley with her partner and three kids. ABOUT CATE HUSTON Cate is the author of The Engineering Leader, fractional CTO at Twill, and engineering leadership coach. She was previously in leadership roles at DuckDuckGo and Automattic, and an advisor at Glowforge. She has been all over the world, but now lives in Ireland. Check out DRI Your Career today and use promo code “ELCPODCAST” for 15% off any of Cate and Jean’s three courses! SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Redefining profit, centering human flourishing, and building an incorruptible mission-driven roadmap w/ Eric Ries #260 | 26 mai 2026 | 00:41:43 | |
In this episode, we’re joined by Eric Ries, creator of The Lean Startup, to discuss insights from his latest book, Incorruptible: Why Good Companies Go Bad… and How Great Companies Stay Great. Eric shares what inspired him to write the book and why we need to move beyond and redefine what true profit looks like. He shares the history behind businesses transitioning from serving public interests to shareholder primacy and why leaving behind a people-first business approach can actually reduce profitability. Additionally, Eric discusses financial gravity, the “harder is easier” principle, and how these practices connect to AI & current engineering leadership challenges. ABOUT ERIC RIES Over the last two decades, Eric Ries’s ideas about continuous innovation, long-term thinking, governance, and market reform have reshaped company building and management practices. He is the creator of the Lean Startup method, and the author of the New York Times bestseller The Lean Startup; The Leader’s Guide; and The Startup Way. As a founder, he has put his own ideas into practice with The Long-Term Stock Exchange (LTSE); Answer.AI, an AI R&D lab; Virgil, a legal services startup; and IMVU. On The Eric Ries Show, he talks with world-class technologists, thought leaders, and executives building for the long-term. He lives in the San Francisco Bay Area with his wife and three children. Unblocked: The context engine your coding agents are missing. Give your coding agents the context your best engineers have. Your agents can read code, but they don’t know how your team works. Rules and MCPs give access to information but not understanding. That’s why you still have to tell them where to look and what to look for. Unblocked gives your agents the history, conventions, and decisions behind your code so they generate mergeable output without the back and forth. It automatically surfaces the right context for every task, so agents stay on track without the set up tax or the correction loops. getunblocked.com/elcSHOW NOTES:
LINKS AND RESOURCES
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Affirm’s AI-native transformation & how it’s driving operational excellence w/ Geddes Munson #259 | 19 mai 2026 | 00:45:04 | |
In this episode, Geddes Munson (SVP of Engineering @ Affirm) joins us to discuss operational / engineering excellence, scaling, and AI-native transformation! We explore Affirm’s approach to operational and engineering excellence and how a 2024 outage became a turning point in refining that focus. We deconstruct “AI retooling week”, the internal tools it inspired (including an incident tracing system), how the AI-native transition is impacting operational / engineering excellence, and how to connect these projects to business goals. Plus, we take a look at their early work building in agentic commerce, infrastructure decisions they made years ago setting them up for success now, how they’re thinking about designing for agent-first experiences. ABOUT GEDDES MUNSON Geddes Munson serves as Affirm’s SVP, Engineering. Previously, Geddes held several engineering leadership roles at Affirm, including oversight of the merchant engineering group, where he was responsible for the development of Affirm’s solutions for key partners including Amazon, Shopify and Walmart. Prior to Affirm, Geddes held various technical leadership roles at rapidly growing startups including Mixpanel, SingleStore and EasyPost. He received his B.A. from Haverford College, where he started the Linux club on campus. Geddes lives in New Jersey with his wife and three children. Unblocked: The context engine your coding agents are missing. Give your coding agents the context your best engineers have. Your agents can read code, but they don’t know how your team works. Rules and MCPs give access to information but not understanding. That’s why you still have to tell them where to look and what to look for. Unblocked gives your agents the history, conventions, and decisions behind your code so they generate mergeable output without the back and forth. It automatically surfaces the right context for every task, so agents stay on track without the set up tax or the correction loops. getunblocked.com/elcSHOW NOTES:
LINKS AND RESOURCES
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Building reliable and proactive agentic systems at scale: how Shopify’s reflexive AI culture was instrumental in their development of Sidekick w/ Andrew McNamara #258 | 12 mai 2026 | 00:37:12 | |
Andrew McNamara, Director of Applied Machine Learning @ Shopify, joins the ELC podcast to share insights on building agentic platforms at scale, like Sidekick, that must keep reliability for its users at the forefront. Andrew describes the building philosophy behind Shopify and what it means to cultivate a culture of prototype-first while prioritizing hiring early-stage talent. We cover Sidekick’s development journey and how user feedback impacted its product vision, why evaluation is so important for determining ground truth sets, and the benefit of user-driven use cases. Andrew also dissects how they went about making product design decisions, such as building proactive agents and identifying subagent specializations. ABOUT ANDREW MCNAMARA Andrew McNamara is Director of Applied Machine Learning at Shopify, where he leads the team behind Shopify Sidekick, an AI co-founder that gives merchants access to the e-commerce expertise they need to run and grow their business. With 16 years of experience building AI assistants, he brings a rare combination of applied research depth and production-scale thinking to some of the hardest problems in AI: getting systems to work reliably for people who depend on them. Andrew's work pushes Shopify to measure AI quality by whether it achieves what the user set out to do, a core standard in building AI that merchants trust. Outside Shopify, he runs Setting North, a small Canadian maple syrup brand built on the same platform he helps make for everyone else. Unblocked: The context engine your coding agents are missing. Give your coding agents the context your best engineers have. Your agents can read code, but they don’t know how your team works. Rules and MCPs give access to information but not understanding. That’s why you still have to tell them where to look and what to look for. Unblocked gives your agents the history, conventions, and decisions behind your code so they generate mergeable output without the back and forth. It automatically surfaces the right context for every task, so agents stay on track without the set up tax or the correction loops. getunblocked.com/elcSHOW NOTES:
LINKS AND RESOURCES
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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 the R&D Org at Twilio Drives Business Strategy and Transformation w/ Inbal Shani #257 | 05 mai 2026 | 00:47:19 | |
Inbal Shani (CPO and Head of R&D @ Twilio) deconstructs the transformation of the R&D org at Twilio! We explore the shift from a GM-led model to a unified platform strategy and “why structure must always follow strategy.” Inbal shares her framework for moving from output-focused metrics to input goals, prioritizing “time-to-value,” and the nuances of measuring AI products. We discuss using "R&D roadshows" as a strategic company transformation tool and why engineering leaders must master product positioning. We also dive into mental models for future-proofing your business, from "working backwards" to solve customer problems, to embedding systems thinking into the DNA of your engineering team, and critical questions to identify and optimize decisions around your company’s moat. ABOUT INBAL SHANI As Chief Product Officer, Inbal leads Twilio's R&D organization, encompassing product, engineering, and R&D operations. She is dedicated to driving platform-wide innovation, empowering customers, and delivering transformative, customer-focused solutions. Unblocked: The context engine your coding agents are missing. Give your coding agents the context your best engineers have. Your agents can read code, but they don’t know how your team works. Rules and MCPs give access to information but not understanding. That’s why you still have to tell them where to look and what to look for. Unblocked gives your agents the history, conventions, and decisions behind your code so they generate mergeable output without the back and forth. It automatically surfaces the right context for every task, so agents stay on track without the set up tax or the correction loops. getunblocked.com/elcSHOW NOTES:
LINKS AND RESOURCES
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Scaling TensorFlow, Navigating Startup Pivots, ML Edge Infrastructure and AI Inference Strategy w/ Rajat Monga #256 | 28 avr. 2026 | 00:40:34 | |
Rajat Monga, CVP AI Frameworks @ Microsoft, joins the podcast to discuss his leadership and founder journey, from Google Brain / Tensorflow to inference.io and back to Microsoft. He dissects what it means to refound vs. start from scratch, the value of the open source community, and strategies for discovering what problem to solve when going the startup route. We also cover how to determine your users’ hidden incentives and what that means for both product development & marketing, along with navigating the balance between a product’s usefulness and consumers’ willingness to pay for it. Additionally, Rajat shares about what he’s currently up to at Microsoft and the emerging ML / AI technologies he’s most excited about. ABOUT RAJAT MONGA Rajat Monga is responsible for enabling an efficient AI stack at Microsoft from cloud to the edge. Before joining Microsoft, Rajat was founder and CEO of Inference.io, a smart analytics platform powered by AI. During his decade-long tenure at Google, he co-founded and led TensorFlow, and was a founding member of Google Brain. He’s built out and led many engineering teams, and designed large scale distributed systems including web scale crawling and eBay’s search engine. Rajat is a graduate of IIT Delhi. Unblocked: The context engine your coding agents are missing. Give your coding agents the context your best engineers have. Your agents can read code, but they don’t know how your team works. Rules and MCPs give access to information but not understanding. That’s why you still have to tell them where to look and what to look for. Unblocked gives your agents the history, conventions, and decisions behind your code so they generate mergeable output without the back and forth. It automatically surfaces the right context for every task, so agents stay on track without the set up tax or the correction loops. getunblocked.com/elcSHOW NOTES:
LINKS AND RESOURCES
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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 Enterprises Actually Win with AI: Operationalizing Responsible AI, Engineering Guardrails, Trust Controls, and Systems Thinking at Scale w/ Murali Swaminathan #255 | 21 avr. 2026 | 00:44:31 | |
Enterprise customers demand 99.9% availability, regardless of how the underlying software is built. In this episode, Murali Swaminathan (CTO @ Freshworks) discusses how enterprises actually win with AI! We explore the “Architecture of Predictability” – proactive architectural safeguards to scale “responsible AI by design” across a global organization serving 75,000 customers. Murali shares his leadership playbook for implementing the technical safeguards and product trust controls that empower hundreds of engineers to build safely. We also dive into the shift from deterministic flowcharts to “workflows with a brain” and why backend systems engineers are the secret bedrock of agentic products. Plus, Murali deconstructs the dual evolution required of modern leaders: mastering strategic thinking at the business level while cultivating systems thinking at the engineering level. ABOUT MURALI SWAMINATHAN Murali Swaminathan joined Freshworks as Chief Technology Officer in September 2024. Murali is responsible for Freshworks’ technology roadmap and strategy, leading the company’s global engineering and architecture teams. With over 30 years of experience in software engineering, he has held leadership roles at ServiceNow, Recommind (now OpenText), and CA Technologies (now Broadcom), where he delivered scalable, secure solutions that enabled digital transformation and business agility. Murali holds a master’s degree in Software Engineering Management from Carnegie Mellon University and a bachelor’s degree in electronics and instrumentation from Annamalai University in India. SHOW NOTES:
LINKS AND RESOURCES
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Shifting Eng Leaders to Think Like GMs, Building an AI-Driven Visionary Roadmap & Braze’s Product Health Initiative w/ Jon Hyman #254 | 07 avr. 2026 | 00:48:35 | |
Jon Hyman (CTO & Co-Founder @ Braze) returns to the podcast to share how he balances a mature, public-company roadmap with visionary AI innovation! We deconstruct Braze’s quantitative "Product Health" framework - a scoring system used to resolve competing prioritizations and mandate technical remediation. We also discuss shifting engineering leaders to think like GMs, how to realign teams by connecting abstract “vision” to specific releases, goals & outcomes. Plus, Jon’s three-tier mental model for AI products, how to identify AI features that actually drive revenue, and reimaging your product for future channels, teams, and skills. ABOUT JON HYMAN Jon Hyman is the co-founder and chief technology officer of Braze, the customer engagement platform that delivers messaging experiences across push, email, in-app, and more. He leads the charge for building the platform’s technical systems and infrastructure as well as overseeing the company’s technical operations and engineering team. Prior to Braze, Jon served as lead engineer for the Core Technology group at Bridgewater Associates, the world’s largest hedge fund. There, he managed a team that maintained 80+ software assets and was responsible for the security and stability of critical trading systems. Jon met cofounder Bill Magnuson during his time at Bridgewater, and together they won the 2011 TechCrunch Disrupt Hackathon. Jon is a recipient of the SmartCEO Executive Management Award in the CIO/CTO Category for New York. Jon holds a B.A. from Harvard University in Computer Science. This episode is brought to you by xMatters! xMatters automates the entire incident lifecycle with their purpose-built AI powered workflow, giving your team the context they need to stop disruptions before they start and minimize resolution times. Head over to xmatters.com to learn more!SHOW NOTES:
LINKS AND RESOURCES
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Leading effectively across company archetypes: product, business and design-led leadership w/ Sebastiano Armeli #253 | 31 mars 2026 | 00:39:46 | |
We discuss what effective leadership looks like across three organizational archetypes: product-led, business-led, and design-led companies with Sebastiano Armeli (Engineering Leadership @ Meta). Drawing from his leadership journey at places like Meta, Spotify, Snap, and PayPal, Sebastiano deconstructs the situational leadership frameworks required to thrive in different environments. Plus we discuss how AI is moving managers from implementation to architecture, why the next bottleneck is managing the overhead of high-velocity experimentation, and the future of team topology where AI enables a single leader to oversee high-scale teams of 30–50 people. Whether you are scaling a design-driven startup or navigating a complex business-led enterprise, this conversation provides a framework for aligning your leadership style with your organization's core incentives. ABOUT SEBASTIANO ARMELI Sebastiano Armeli is an engineering leader currently at Meta. He has previously served as a Director of Engineering at Upwork and held leadership roles at companies such as Pinterest, PayPal, Snap, and Spotify. His work has spanned diverse domains including shopping, crypto, messaging, video creation, and ads. Sebastiano is passionate about building healthy engineering cultures, mentoring the next generation of leaders, and supporting teams through periods of growth and change. He mentors engineering managers and senior engineers, enjoys speaking at conferences, and shares his perspectives on leadership in his Substack, The Healthy Engineering Leader. He also serves on the board of a community-owned grocery store. In all his work, Sebastiano takes a pragmatic, people-first approach to leadership, focusing on clarity, continuous improvement, and long-term impact. This episode is brought to you by xMatters! xMatters automates the entire incident lifecycle with their purpose-built AI powered workflow, giving your team the context they need to stop disruptions before they start and minimize resolution times. Head over to xmatters.com to learn more!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Changes in engineering management craft, career growth and all hands demos for inspiration and context w/ Lindsey Simon #252 | 24 mars 2026 | 00:45:25 | |
Live from the Vercel recording studio, Lindsey Simon (VP Engineering @ Vercel) joins us to deconstruct the evolution of management craft and career growth strategies! We dissect the practice of live all-hands demos as a tool for context, accountability and inspiration. Plus, Lindsey’s "vote with your wallet" framework for career strategy, how Lindsey’s open source project inspired him to apply to Vercel, and why the most effective VPs are building hobby projects to maintain AI competency and empathy for non-technical users. ABOUT LINDSEY SIMON Lindsey Simon is VP of Engineering at Vercel. Making the Web better has been his lifelong career ambition. Prior to Vercel, Lindsey spent seven years at Google, where he helped launch App Engine as an original core team member, and worked as a tech lead on the Google Translate and Web Performance teams. Lindsey has lived in San Francisco for the past 15 years, and his creative hobbies (beyond coding) include writing music and hunting for wild mushrooms. This episode is brought to you by xMatters! xMatters automates the entire incident lifecycle with their purpose-built AI powered workflow, giving your team the context they need to stop disruptions before they start and minimize resolution times. Head over to xmatters.com to learn more!SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Career growth for engineering leaders in the AI era: Building your thesis, the “running framework” & developing technical depth w/ Chris Chiu #251 | 19 mars 2026 | 00:43:51 | |
Career progression is rarely a straight line. More often, it only makes sense in hindsight. Chris Chiu (VP of Engineering, Agentforce @ Salesforce) joins us to deconstruct how to navigate these non-linear career paths! We talk about identifying the mismatch in your current role, building a personal "career thesis," how to engineer a productive exploration phase and leverage your relationships / VC networks to understand the market. Plus, how to apply the "Running Framework" to ensure success in your next role and why technical depth is no longer optional for modern engineering leaders. ABOUT CHRIS CHIU Chris Chiu is a VP of Engineering at Salesforce, where he helps build Agentforce, a platform for building enterprise AI agents. Prior to Salesforce, Chris was Head of Engineering at Moonhub, building AI recruiting agents. He has experience building and scaling product engineering teams that consistently deliver great products through rapid growth and change. Earlier in his career, he led engineering teams across companies ranging from early-stage startups to late-stage growth companies, including Figma, Flexport, and OpenGov. This episode is brought to you by xMatters! xMatters automates the entire incident lifecycle with their purpose-built AI powered workflow, giving your team the context they need to stop disruptions before they start and minimize resolution times. Head over to xmatters.com to learn more!SHOW NOTES:
LINKS AND RESOURCES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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 OpenAI’s engineering org is reshaping teams, roles and workflows w/ Sulman Choudhry #250 | 10 mars 2026 | 00:43:43 | |
In this episode, recorded live at the OpenAI studio, Sulman Choudhry (Head of ChatGPT @ OpenAI) pulls back the curtain on how they structure engineering teams! We talk about shifting from silos to fluid mission-driven teams, vertical vs. horizontal teams, maximizing cross-functional collaboration between research, engineering, product and design. Plus we cover “directly responsible individuals” for high accountability, managers as systems designers, scaling decision-making to prevent leadership from becoming bottlenecks, frameworks for mentoring junior engineers, why “problem framing” is the most critical skill, and how managers can stay close to problems and maintain technical intuition. ABOUT SULMAN CHOUDHRY Sulman 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. This episode is brought to you by xMatters! xMatters automates the entire incident lifecycle with their purpose-built AI powered workflow, giving your team the context they need to stop disruptions before they start and minimize resolution times. Head over to xmatters.com to learn more!SHOW NOTES:
LINKS AND RESOURCES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| The innovation engine behind Samsara driving real-world impact: compounding feedback loops, data flywheels and embedding engineers in customer problems w/ Kiren Sekar #249 | 17 févr. 2026 | 00:43:34 | |
Kiren Sekar (CPO @ Samsara) joins us to deconstruct the "Innovation Engine" behind Samsara, and how this system drives real-world impact and ROI across their products. We explore Samsara’s decade-long compound product strategy and the mechanics of accelerating feedback loops in an era where the primary bottlenecks shift from code generation to customer feedback and absorption of change. Kiren details how their data flywheel expands the aperture of what is possible to build and we dive into the system of customer-driven innovation: advisory boards, “spark sessions” to test hypotheses and gain unfiltered feedback. Plus we talk about the power of embedding engineers in frontline environments (from truckyards to construction sites) to cultivate “taste,” customer empathy and trigger non-linear ideas. ABOUT KIREN SEKAR Kiren Sekar is the Chief Product Officer at Samsara (NYSE: IOT), where he has helped lead the company from a hardware-hacking startup in a basement to a global leader in Connected Operations with over $1.5B in ARR. An early leader at Meraki (acquired by Cisco for $1.2B) and an Apple veteran with multiple patents, Kiren specializes in the rare intersection of hardware, massive-scale data, and AI. He is the architect of a platform that now processes trillions of data points for the industries that keep the world running—trucking, construction, and logistics. This episode is brought to you by Retool! What happens when your team can't keep up with internal tool requests? Teams start building their own, Shadow IT spreads across the org, and six months later you're untangling the mess… Retool gives teams a better way: governed, secure, and no cleanup required. Retool is the leading enterprise AppGen platform, powering how the world's most innovative companies build the tools that run their business. Over 10,000 organizations including Amazon, Stripe, Adobe, Brex, and Orangetheory Fitness use the platform to safely harness AI and their enterprise data to create governed, production-ready apps. Learn more at Retool.com/elcSHOW NOTES:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Why founders should invest in coaching, communication & leadership mechanisms before you scale w/ James Birchler #248 | 10 févr. 2026 | 00:50:46 | |
Founders often delay leadership coaching until a major crisis hits, leading to significant costs in productivity, team churn, and poor decisions. In this episode, James Birchler (Technical Advisor & Executive Leadership Coach) argues that early coaching is a game-changer for a startup's success. We explore the hidden costs of waiting and the benefits of intentionally installing leadership and communication systems before you scale. James shares specific self-awareness mechanisms, like advisory groups and feedback loops, to help founders design their day and create accountability. You'll also learn practical strategies like the "5-Minute Alignment Loop" for spotting communication breakdowns & for reinforcing clarity. Plus insights on how to "install your leadership OS" so it can scale with your company. ABOUT JAMES BIRCHLER James Birchler is an executive leadership coach and technical advisor who specializes in helping engineering leaders and founders develop greater self-awareness and build high-performing teams. He combines deep technical expertise with practical leadership development, making him particularly valuable for technical leaders scaling their organizations. As both a founder and engineering leader, James has more than 20 years of experience leading teams at companies ranging from early-stage startups to Amazon, where his current role is Technical Advisor to the VP of Amazon Delivery Routing and Planning. Most recently, he founded NICER, a premium natural personal care company, and Actuate Partners, his executive coaching and technical advisory practice. He also held VP of Engineering roles at companies including Caffeine (backed by Greylock and Andreessen Horowitz), SmugMug (where his team acquired Flickr), and IMVU. At IMVU, James implemented the Lean Startup methodologies alongside Eric Ries, author of The Lean Startup and creator of the methodology, literally the first company to apply these principles. His team helped pioneer the DevOps movement by building infrastructure to ship code to production 50 times per day and coining the term "continuous deployment." This experience in systematic experimentation and continuous improvement now informs his coaching approach through frameworks like CAMS (Coaching, Advising, Mentoring, Supporting) and the Think-Do-Learn Loop. James completed his executive coaching certification at UC Berkeley Haas School of Business Executive Coaching Institute. His coaching practice focuses on self-awareness, integrity, accountability, and fostering growth mindsets that support continuous learning and high performance. He writes the Continuous Growth newsletter and offers both individual executive coaching and peer learning circles for technical leaders. Through his advisory work with growth-stage startups in the US and Europe, James helps leaders navigate common scaling challenges including hiring and interviewing, implementing development methodologies, establishing operational cadences, and developing other leaders. His approach treats leadership development like product development—with systematic feedback loops, measurable outcomes, and continuous improvement. You can find James at jamesbirchler.com, LinkedIn, and Substack. This episode is brought to you by Retool! What happens when your team can't keep up with internal tool requests? Teams start building their own, Shadow IT spreads across the org, and six months later you're untangling the mess… Retool gives teams a better way: governed, secure, and no cleanup required. Retool is the leading enterprise AppGen platform, powering how the world's most innovative companies build the tools that run their business. Over 10,000 organizations including Amazon, Stripe, Adobe, Brex, and Orangetheory Fitness use the platform to safely harness AI and their enterprise data to create governed, production-ready apps. Learn more at Retool.com/elcSHOW NOTES:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Cultivating product thinking, cross-functional leadership & the future of AI agent infrastructure w/ Jaikumar Ganesh #247 | 05 févr. 2026 | 00:49:43 | |
In our latest ELC episode, we are addressing some of the biggest challenges facing engineers today: identifying your scaling thesis, putting that thesis into practice, and addressing implementation challenges. Jaikumar Ganesh, Head of Engineering @ Anyscale, shares insights from his experience working at top tech companies like Android and Uber, and how to apply those lessons within your own orgs. We also cover strategies for identifying what to build, using data effectively when it comes to understanding AI agents, and keeping your intent (and customer success) top of mind. Additionally, Jaikumar discusses his experience as a GM and why all orgs should adopt cross-functional skillsets as part of their company culture. ABOUT JAIKUMAR GANESH Jaikumar Ganesh is an accomplished technology leader and the Head of Engineering at Anyscale. With a deep background in engineering and customer-facing roles, Jaikumar has a proven track record of building and scaling engineering organizations. He is passionate about pushing the boundaries of product and engineering innovation while ensuring customer needs are met, and is committed to building empowering organizations rooted in trust, respect, and growth. Jaikumar is excited about working with companies to harness the power of AI and distributed computing to achieve their goals. He previously co-started and co-led Uber's AI group—the central ML group at Uber—and was also on the early team at Android @ Google. This episode is brought to you by Retool! What happens when your team can't keep up with internal tool requests? Teams start building their own, Shadow IT spreads across the org, and six months later you're untangling the mess… Retool gives teams a better way: governed, secure, and no cleanup required. Retool is the leading enterprise AppGen platform, powering how the world's most innovative companies build the tools that run their business. Over 10,000 organizations including Amazon, Stripe, Adobe, Brex, and Orangetheory Fitness use the platform to safely harness AI and their enterprise data to create governed, production-ready apps. Learn more at Retool.com/elcSHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Scaling from point solutions to a unified, AI-powered product ecosystem w/ Vineeta Puranik #246 | 27 janv. 2026 | 00:36:51 | |
How do you transform a collection of individual tools into a cohesive, AI-powered symphony? Vineeta Puranik (CPTO @ SmartBear) dissects the strategy behind evolving a product vision from point solutions to a unified multi-product ecosystem. We explore the critical architectural distinction between "AI bolt-on" and "AI native" strategies, frameworks for seamless M&A integration, and how to design for varying levels of customer AI readiness. Vineeta also discusses the shift to test “does it match intent”, using “jobs to be done” to drive solving entire workflows not just tool capabilities, and designing user experiences for both human personas and AI agents. ABOUT VINEETA PURANIK Vineeta Puranik serves as Chief Product and Technology Officer (CPTO) at SmartBear, where she leads the company’s global technology and product strategy to empower developers and enterprises worldwide. A seasoned technology executive with over two decades of experience, she combines strategic vision with hands-on leadership to drive innovation, growth, and operational excellence. At SmartBear, Vineeta oversees development, cloud engineers, AI, and architecture, and has been instrumental in scaling centers of excellence in India and Poland, launching the Developer Academy, and advancing the company’s hub-based product strategy – Swagger suite for API capabilities, Test Hub, and Insight Hub. Recognized for her collaborative, people first leadership and commitment to inclusion, she was named a 2024 Women Worth Watching in STEM by Profiles in Diversity Journal. This episode is brought to you by Retool! What happens when your team can't keep up with internal tool requests? Teams start building their own, Shadow IT spreads across the org, and six months later you're untangling the mess… Retool gives teams a better way: governed, secure, and no cleanup required. Retool is the leading enterprise AppGen platform, powering how the world's most innovative companies build the tools that run their business. Over 10,000 organizations including Amazon, Stripe, Adobe, Brex, and Orangetheory Fitness use the platform to safely harness AI and their enterprise data to create governed, production-ready apps. Learn more at Retool.com/elcSHOW NOTES:
LINKS AND RESOURCES Books Mentioned
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| From localized to systematic speed: How Spotify deploys AI in prototyping, strategy & maintenance w/ Tyson Singer #245 | 21 janv. 2026 | 00:44:28 | |
Tyson Singer (Head of Tech & Platforms @ Spotify) joins us to unpack how Spotify is transforming its product development lifecycle across creation, experimentation and maintenance to shift from "localized speed" to "systematic speed." We explore why the industry’s current obsession with the "Build It" phase of development is shortsighted, and how Spotify is aggressively deploying AI in the "Think It" (prototyping/strategy) and "Maintain It" (fleet management) phases. Tyson also details the internal tools driving this shift, including AiKA and Honk, and shares why the future of engineering relies on moving from I-shaped specialists to T-shaped generalists. ABOUT TYSON SINGER Tyson Singer is the SVP of Technology & Platforms at Spotify, where he leads technology infrastructure, developer experience, cybersecurity, and finance IT. Tyson is the executive behind Spotify’s internal developer portal, Backstage, and Spotify’s experimentation system, Confidence, which are now both commercially available. He has a background as an engineer, architect, and product lead, and he holds a Master’s in Computer Science from Stanford University. Tyson is also an avid outdoor adventurer. This episode is brought to you by Retool! What happens when your team can't keep up with internal tool requests? Teams start building their own, Shadow IT spreads across the org, and six months later you're untangling the mess… Retool gives teams a better way: governed, secure, and no cleanup required. Retool is the leading enterprise AppGen platform, powering how the world's most innovative companies build the tools that run their business. Over 10,000 organizations including Amazon, Stripe, Adobe, Brex, and Orangetheory Fitness use the platform to safely harness AI and their enterprise data to create governed, production-ready apps. Learn more at Retool.com/elcSHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Inside ELC’s 1st Hackathon: Deconstructing the operational playbook, implementation lessons & future of the program w/ James Tyack #244 | 13 janv. 2026 | 00:32:39 | |
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 TYACK James Tyack leads the Learner Success and Visual Experience teams at Coursera, creating engaging and personalized learning experiences for millions of learners worldwide. An avid user of Coursera and a lifelong learner himself, James is passionate about leveraging technology, including AI, to transform lives through education. Prior to Coursera, he led integration and growth teams at PagerDuty, driving innovation and adoption of incident response tools and best practices. Beyond his professional work, James is the chapter lead for the South Bay Engineering Leadership Community (ELC) group, fostering collaboration among tech leaders. He is also a proud dad to a one-year-old, balancing his career and personal life with a deep commitment to growth and connection. 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:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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 is leadership in the AI Era? w/ Bill Coughran & Bret Reckard #243 | 06 janv. 2026 | 00:20:32 | |
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 COUGHRAN Bill 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:
LINKS AND RESOURCES This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| From Research Lab to Record-Breaking Product: How OpenAI Engineered for Unprecedented Scale w/ Sulman Choudhry, Samir Ahmed & Lawrence Bruhmeller #242 | 30 déc. 2025 | 00:25:28 | |
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 CHOUDHRY Sulman 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:
LINKS AND RESOURCES This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| The AI Distribution Shift, Navigating PMF Collapse & Building AI-Native EPD Systems w/ Brian Balfour #241 | 23 déc. 2025 | 00:46:04 | |
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 BALFOUR Brian 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 Balfour’s Research & Frameworks
Reforge Strategic Deep Dives
Mentions This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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 Atlassian built Rovo in 6 months: systematizing developer joy, autonomy/ownership, productivity champions & reducing ship time w/ Rajeev Rajan #240 | 17 déc. 2025 | 00:46:37 | |
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 RAJAN Rajeev 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:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| From developer to builder/system designer, managing AI agents like team members & monday.com’s evolving R&D playbook w/ Daniel Lereya #239 | 09 déc. 2025 | 00:47:39 | |
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 LEREYA Daniel 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:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Beyond Replication: Building Non-Human Intelligence Through Physical AI w/ Jaime Lien & Rashi Agrawal #238 | 04 déc. 2025 | 00:24:19 | |
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 LIEN Jaime 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 AGRAWAL Rashi 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:
LINKS AND RESOURCES This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Specs as the new source of truth, synthetic data as the next wave of defensibility, product vision & decision making frameworks w/ Ruslan Belkin #237 | 20 nov. 2025 | 00:51:54 | |
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 BELKIN Ruslan 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:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Brex 3.0: An 18-Month Operational Evolution & the Brex Hacker House “AI Startup within a Startup" experiment w/ James Reggio #236 | 12 nov. 2025 | 00:45:30 | |
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 REGGIO James 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:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| The Impossible Job of Managers, Leadership Co-Pilots, Scaling Great Management & Augmenting Human Relationships w/ Jonathan Raymond #235 | 05 nov. 2025 | 00:52:09 | |
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 RAYMOND 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. SHOW NOTES:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| A Systems-Level Guide to High-ROI AI Impact w/ Laura Tacho #234 | 29 oct. 2025 | 00:44:23 | |
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:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Platform Engineering's Shift from Tactical 'How' to Strategic Curator & Natural Language as the New Interface Paradigm w/ Miriam Aguirre #233 | 21 oct. 2025 | 00:44:20 | |
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 Agents So 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.devSHOW NOTES:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Grit, the vision bottleneck & building for a future where today’s technical constraints may disappear w/ Chrystal Henke Ball #232 | 15 oct. 2025 | 00:49:27 | |
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 BALL Chrystal 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 Agents So 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.devSHOW NOTES:
LINKS AND RESOURCES
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Leading across technical domains, strategic deep-dives & applying your skills in new industries w/ Simone Kalmakis #231 | 09 sept. 2025 | 00:43:17 | |
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 Agents So 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.devJoin us at ELC Annual 2025 ELC 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/annual2025SHOW NOTES:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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 Box Builds AI Agents, Redefines Technical Vision, and Balances Speed with Security w/ Ben Kus #230 | 26 août 2025 | 00:46:14 | |
"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 KUS Ben 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 Agents So 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.devJoin us at ELC Annual 2025 ELC 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/annual2025SHOW NOTES:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Rewriting the Engineering Leadership Playbook: An ELC Annual 2025 Preview #229 | 19 août 2025 | 00:23:09 | |
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/annual2025 Use code podcast15 for 15% off tickets - group tickets / discounts available. ABOUT ELC ANNUAL The 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% off Group 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 Agents So 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.devJoin us at ELC Annual 2025 ELC 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/annual2025SHOW NOTES:
This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| The End-to-End Engineer: How WorkOS Collapsed the Talent Stack for High-Velocity Execution, Ownership & Better Product Decisions w/ Michael Grinich | 05 août 2025 | 00:44:55 | |
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 Agents So 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.devJoin us at ELC Annual 2025 ELC 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/annual2025SHOW NOTES:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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: What every engineering leader can learn from security w/ Srinath Kuruvadi #227 | 22 juil. 2025 | 00:37:02 | |
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/annual2025SHOW NOTES:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Vision-first leadership & reimagining product w/ “Shift Out,” Do-It-as-a-Service & Jobs-to-Be-Done w/ John Amaral #226 | 08 juil. 2025 | 00:44:54 | |
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 2025 ELC 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/annual2025SHOW NOTES:
Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah 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. | |||
| Quick Summer Break! Join us @ ELC Annual 2025 (Early Bird Tickets End Soon) | 01 juil. 2025 | 00:02:46 | |
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.
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