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Données mises à jour le 14/10/2026
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Building your support network, picking the right projects, and why eng leaders make good investors w/ Amit Gupta #272
mardi 13 octobre 2026 • Durée 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.
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.
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
mardi 6 octobre 2026 • Durée 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.
Zohar 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.
Utilizing AI to assist in EPD and non-EPD functions & how curiosity can drive organizational change w/ Ali Dasdan #270
mardi 29 septembre 2026 • Durée 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)
Implementing scalable and powerful agentic tools across your organization w/ Ozzie Osman #269
mercredi 23 septembre 2026 • Durée 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
jeudi 17 septembre 2026 • Durée 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)
How to control the scope while scaling / rebuilding (10:16)
Hiring top-tier talent, leveraging open source models, and staying competitive in the age of AI w/ Benny Chen #267
mercredi 2 septembre 2026 • Durée 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
mardi 25 août 2026 • Durée 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
mardi 4 août 2026 • Durée 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
mardi 21 juillet 2026 • Durée 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
mardi 7 juillet 2026 • Durée 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)
SHOW NOTES:
Introducing Zohar & his background / main focus (1:02)
Defining what a software factory is & what that means for the industry (1:50)
Parallels between a physical factory vs. a software factory (3:50)
How the software factory model impacts organizational structure (5:27)
What certification means in the context of software factories (8:46)
Best practices for building a new software factory (10:48)
Don’t make the ability to scale an afterthought (12:15)
Navigating the balance between control & automation when building from scratch (13:17)
How to know when a team / function merits its own software factory (14:37)
Transitioning from a pre-AI to post-AI world as a large company (16:18)
Inside Port’s rebuild using AI & navigating the team through the transition (18:00)
The team’s reaction to building for agents vs. humans (20:25)
Approaching decision-making with a healthy dose of trepidation (21:48)
Characteristics that make for good hires today (22:51)
Examples of product-related decisions that felt scary in the moment (25:03)
Lessons learned while Port transitioned to building for agents (27:27)
How to measure the ROI of software factories (29:05)
Insights on how to best allocate resources across a mature company (31:10)
Hiring hungry, young talent vs. hiring established talent (32:56)
Rapid fire questions (35:30)
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.
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:
Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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