We share the most critical perspectives, habits & examples of great software engineering leaders to help evolve leadership in the tech industry.
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The Engineering Leadership Podcast, a podcast by The Engineering Leadership Community (ELC) - Stats, Episodes and Rankings - My Podcast Data
Utilizing AI to assist in EPD and non-EPD functions & how curiosity can drive organizational change w/ Ali Dasdan #270
Tuesday, September 29, 2026 • Duration 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.
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:
Why Ali continues to publish research as a CTO (1:51)
How research results can alter decision making as an eng leader (3:30)
The connection between research & organizational trust (4:29)
Redrawing the org’s architecture to learn more about it (6:00)
What kinds of info help eng leaders better understand the business / technology (8:12)
Building a record of the org’s progress & development (10:13)
Where Dropbox is at in their AI adoption journey (11:58)
AI @ Dropbox in EPD vs. non-EPD functions (13:36)
Frameworks for implementing AI at the highest level (15:23)
The engagement / ownership model @ Dropbox (16:58)
Insights on Nova, Dropbox’s code review AI workflow (18:59)
Incorporating human-driven feedback into the AI loop (21:12)
What the immediate future looks like for automated developer tools (23:54)
How AI has directly impacted productivity @ Dropbox (27:15)
Addressing bottlenecks related to AI adoption (30:35)
Using AI infrastructure to assist in non-EPD functions (32:33)
Dash as a contextual AI platform (35:39)
Ali’s experience with specialized models vs. foundation models (38:10)
Rapid fire questions (39:48)
This episode wouldn’t have been possible without the help of our incredible production team:
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
Wednesday, September 23, 2026 • Duration 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.
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.
Navigating from individual AI adoption to team-level transformation while scaling w/ Jakub Oleksy #268
Thursday, September 17, 2026 • Duration 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.
The current focus @ Github & what scaling looks like (1:21)
Signals that previous scaling methods are no longer viable (3:00)
Migrating to Azure / impact on the engineering org (5:55)
Strategies for orchestrating massive, widespread change across the org (7:28)
Hiring top-tier talent, leveraging open source models, and staying competitive in the age of AI w/ Benny Chen #267
Wednesday, September 2, 2026 • Duration 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.
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!
Check it out !
Applying Agentic AI to the Supply Chain, Building Systems to Withstand Chaos, and Leveraging your Curiosity w/ Pooja Brown #266
Tuesday, August 25, 2026 • Duration 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.
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.
Check it out !
Hiring top-tier talent, the importance of adopting an evolutionary mindset, and taking critical feedback to solve technical problems w/ Sergiy Nesterenko #265
Tuesday, August 4, 2026 • Duration 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.
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:
Introducing Sergiy Nesterenko & the inspiration behind Quilter (1:43)
Why now is the right time to tackle this technical challenge (3:37)
The technology landscape during Quilter’s early days (6:05)
The importance of adopting an evolutionary mindset (10:52)
Early problems that Quilter aimed to solve (13:08)
Navigating the balance between technical problems & consumer readiness (15:59)
How negative feedback can lead to solving a key problem (18:34)
Knowing which feedback to incorporate into product iterations (20:08)
Lessons learned from choosing the wrong customers (27:33)
Determining bets, using customer insights to pivot, and gaining developer buy-in & trust w/ Tomas Reimers #264
Tuesday, July 21, 2026 • Duration 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.
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:
The origin story behind Graphite (1:05)
Signs that it’s time to quit your job / found a company (4:03)
How Tomas & his co-founders knew it was time to break up with their jobs (5:40)
Understand what leaving your job will mean career-growth wise (7:33)
Embracing regret minimization (9:28)
Pros & cons of developing in blue ocean vs. red ocean areas as a founder (11:49)
Strategies for determining what software to build / how is software dev evolving (14:00)
Tomas’s framework for determining bets (15:50)
Recommendations for selling as a founder (17:52)
Identifying if sales isn’t working or if product market fit is off (20:35)
Using customer insights to experiment & make a PMF pivot (23:05)
Why developers don’t want to be sold to, they want to be taught (24:42)
How to apply teaching vs. selling into early GTM strategy (27:20)
Utilizing demonstrations to gain developer buy in & trust (29:24)
What Tomas is looking forward to in Graphite’s future / software dev in general (32:04)
LINKS AND RESOURCES
Utilizing AI internally to iterate faster and empower smaller teams to upskill w/ Vivek Raghunathan #263
Tuesday, July 7, 2026 • Duration 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.
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.
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:
Where Snowflake is on their AI adoption journey (0:57)
Using AI to help eng orgs meet maximum velocity (3:04)
Defining traits of engineers who successfully leverage agentic tools (5:55)
The benefit of cross collaborative skillsets for eng leaders (8:53)
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
Tuesday, June 23, 2026 • Duration 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.
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.
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:
The product paradigm shift toward voice-driven apps and natural human-computer interfaces (2:44)
Voice-apps in practice: How these trends impact the strategy of product building today (5:32)
Early adopters: Why legacy industries like healthcare use voice AI (7:55)
Reevaluating and building product experiences optimized for AI agents (12:52)
How AI trends will impact roadmaps and Go To Market (18:16)
Building an empowered career w/ Jean Hsu & Cate Huston #261
Wednesday, June 10, 2026 • Duration 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.
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.
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:
What it means for creative career paths to become the norm (1:42)
Navigating the tension between individual vs. team productivity (3:34)
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Spotify
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SHOW NOTES:
Introducing Ozzie & his role @ Monarch (2:37)
Where Monarch is at in terms of technology transformation / user adoption (5:20)
Insights on how Monarch is embracing AI with a security-forward mindset (7:21)
What it looks like to pursue both agent- and human-orchestrated AI pipelines (11:00)
Dissecting how an MCP shared infrastructure improves productivity (13:11)
Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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.
Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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.
Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
Rapid fire questions (33:34)
The Mom Test - Rob Fitzpatrick’s quick, practical guide that will save you time, money, and heartbreak.
Founding Sales - The Startup Sales Handbook - rhe distillation of Pete Kazanjy’s experience at his first software startup, TalentBin going from a founder with a product marketing and product management background to early sales guy, early sales manager, and eventual post-acquisition sales leader at Monster Worldwide in addition to his later experience founding Modern Sales, the nation’s largest sales operations, enablement, and leadership community.
Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts - Annie Duke, a former World Series of Poker champion turned business consultant, draws on examples from business, sports, politics, and (of course) poker to share tools anyone can use to embrace uncertainty and make better decisions.
This episode wouldn’t have been possible without the help of our incredible production team:
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