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/elc

SHOW NOTES:

• Defining operational excellence & what it looks like @ Affirm (4:36)
• Understand why your company / product matters to your customers (8:11)
• Key pivot points around engineering excellence @ Affirm (11:10)
• Creating a genuine culture change of operational / engineering excellence (14:27)
• Adopting agentic models @ Affirm (16:30)
• Navigating the balance between transformation, safety & reliability (18:30)
• Affirm’s AI retooling week & hackathon setup (20:57)
• How the hackathon helped quickly change the company culture (23:15)
• Ensuring your practices serve your overall organizational vision & goals (26:11)
• Insights on scaling & increasing CICD investment @ Affirm (28:28)
• Approaches to building agentic commerce products (30:11)
• Strategies for building an agent-first experience (33:33)
• Bridging the gap between engineering & business goals / outcomes (35:44)
• Rapid fire questions (38:46)

LINKS AND RESOURCES

• 1929: Inside the Greatest Crash in History – and How It Shattered a Nation - New York Times bestselling author Andrew Ross Sorkin takes readers inside the chaos of the crash, behind the scenes of a raging battle between Wall Street and Washington and the larger-than-life characters whose ambition and naivete in an endless boom led to disaster. The dizzying highs and brutal lows of this era eerily mirror today’s world—where markets soar, political tensions mount, and the fight over financial influence plays out once again.
• Delivering Happiness: A Path to Profits, Passion, and Purpose - a best-selling 2010 memoir by former Zappos CEO Tony Hsieh detailing his entrepreneurial journey and outlines his core philosophy: building a phenomenal corporate culture and focusing on the happiness of employees and customers ultimately drives long-term profits and business success.

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.

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/elc

SHOW NOTES:

• How Shopify utilizes reflexive AI & Andrew’s building philosophy (2:38)
• Developing a prototype-first company culture (5:07)
• Andrew’s reflections on building AI-enabled projects like Sidekick at scale (7:25)
• Translating customer surveys into Sidekick’s product vision (9:34)
• Key inflection points while scaling out Sidekick (11:23)
• Strategies for evaluation / building a ground truth set (13:26)
• Analyzing the good & bad within ground truth sets (15:27)
• Shopify’s system openness model to drive user-discovered use cases (17:47)
• How subagents fit into the Sidekick’s model (19:55)
• Prioritization conversations around subagent specializations (23:06)
• Designing an agent with high-impact prompt optimization (27:22)
• Considerations for building highly reliable systems (29:40)
• Andrew’s perspective on latency (31:24)
• Rapid fire questions (33:49)

LINKS AND RESOURCES

• Cradle - a New York Times best-selling series from Will Wight following a character's growth as he goes from one of the weakest users of his world's magic to among the strongest. The series features an original magic system inspired by Chinese cultivation and martial arts novels, with a heavy emphasis on anime-style super-powered battles.

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.

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/elc

SHOW NOTES:

• Catalysts for Twilio's R&D transformation and the shift away from organizational silos (2:49)
• Strategy Drives Structure: The lightbulb moment at a strategy offsite that demanded structural change to execute vision (5:14)
• Why structure must follow strategy and creating a "change-constant" culture (7:23)
• Implementing the “working backwards” methodology and the internal power of the PRFAQ (13:52)
• Tactical ways to filter customer signals and find real unmet problems versus feature requests (16:35)
• Shifting from output-focused goals to input goals and prioritizing "Time to Value" (18:35)
• Using weekly product reviews to align metrics with qualitative customer feedback (21:34)
• Measuring AI Products: Why AI products require behavior-based measurement instead of traditional binary testing (23:24)
• Building security by design with layered protection for AI-generated code environments (26:09)
• Mental models for future-proofing your business by acting as a "fortune teller" for needs (28:45)
• The R&D Roadshow: Enabling the entire company on new ways of working through storytelling (32:28)
• Why engineering leaders must master product positioning to bridge the gap to market (38:33)
• Relatable storytelling: Explaining Twilio’s value to your parents to sharpen your pitch (41:47)
• Rapid Fire Questions (43:14)

LINKS AND RESOURCES

• How Minds Change: The Surprising Science of Belief, Opinion, and Persuasion - In this lively journey through human psychology, bestselling author and creator of the You Are Not So Smart podcast David McRaney investigates how minds change--and how to change minds.

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.

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/elc

SHOW NOTES:

• Rajat’s journey with Google Brain: Scaling deep learning from single PCs to thousands of machines with Jeff Dean & Andrew Ng (2:57)
• Moving from Google Brain to TensorFlow: Why new hardware and architectures required a total system rebuild (6:02)
• The "refounding" question: Choosing between starting from scratch or evolving an existing system (8:33)
• Why Google open-sourced TensorFlow to set industry standards and avoid supporting external copies (10:16)
• How open-source enabled global innovation, from Japanese cucumber sorting to African plant health (12:02)
• Transitioning as a leader: Why Rajat left Google during the height of TensorFlow to found a company (13:57)
• The discovery phase at inference.io: Navigating the pivot from IoT into solving data analytics gaps (15:31)
• Lessons on PMF: Moving beyond a "useful" product to one that solves a truly critical customer pain point (16:52)
• Why habits are harder to change than technology and the challenge of competing with established workflows (21:02)
• Marketing strategies: Tailoring personas for top-down prestige versus bottom-up personal efficiency (23:19)
• Deciding when to stop: A founder’s framework for re-evaluating bets based on current knowledge (24:57)
• Rajat’s new role at Microsoft: Overseeing Edge infrastructure and large-scale Cloud AI inference (27:46)
• Dissecting ML edge strategy: Using ONNX Runtime to unify AI performance across Windows, iOS, and Android (30:02)
• Edge AI trends: Shifting from experimental models to production models optimized for cost and privacy (31:20)
• The future of Edge: How on-device processing will power AI in robotics, smart glasses, and wearables (33:23)
• Scaling inference: Treating multi-GPU clusters like a distributed operating system for AI models (34:25)
• Rapid fire questions (37:45)

LINKS AND RESOURCES

• Epic Disruptions: 11 Innovations That Shaped Our Modern World - Innovation expert Scott Anthony masterfully weaves together the fascinating stories behind history's most transformative disruptions—from ninth-century China to twenty-first-century Silicon Valley. Through eleven pivotal innovations, including the printing press, mass-produced automobiles, the McDonald's revolutionary food system, and the iPhone, Anthony reveals the hidden patterns behind world-changing breakthroughs.

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.

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:

• Freshworks' operating context: Engineering for 75,000 global customers (2:09)
• Navigating the tension between rapid AI adoption and enterprise-grade reliability (4:58)
• Breaking the "Positive Scenario" Trap: Using AI to automate negative test cases and corner-case detection (6:40)
• Why Responsible AI is a competitive advantage: Building "kill switches" and trust gates (8:31)
• Responsible AI by Design: Moving from reactive compliance to proactive architectural safeguards (10:48)
• Technical safeguards: Leveraging hyperscaler frameworks for model compliance and data anonymization (13:39)
• Product Trust Controls: Demonstrating reliability through role-based access and thresholds (16:25)
• Why engineering leaders should experiment in small teams before global rollout (20:35)
• Simulating Chaos: Using Business Continuity Planning (BCP) to test AI system resilience (22:13)
• Workflows with a brain: Transitioning from deterministic flows to agentic runtime decisions (24:16)
• The AI Team Profile: Why backend system engineers, not just data scientists, are the bedrock of agentic products (29:25)
• Cultivating a mindset shift toward agentic system orchestration (32:10)
• The shift to systems thinking: How engineering roles evolve from "building pieces" to managing end-to-end system flows (33:38)
• How to approach strategic business thinking as an engineering leader (36:43)
• Rapid Fire Questions: Guy Kawasaki’s "Think Remarkable" and the best way to predict the future (38:23)

LINKS AND RESOURCES

• Think Remarkable: 9 Paths to Transform Your Life and Make a Difference - Tech titan and creator of the Remarkable People podcast Guy Kawasaki delivers a practical, tactical, and sometimes radical discussion of how to make a difference in the world and live a fulfilling life.

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.

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:

• Braze’s operating environment & key focus on product health / roadmap (2:58)
• What’s next for Braze: Research-driven innovation in the AI era (6:16)
• Ensuring customers utilize the full breadth of features (9:42)
• The "Swarming" strategy: Reducing engineering escalation tax through support collaboration (14:19)
• Shifting engineering leadership think like GMs: Moving from completion goals to business outcomes like revenue, growth rates & regional differences (17:29)
• How engineering leaders can increase business IQ by understanding margins and adoption (18:20)
• Deconstructing misalignment, the abstract nature of product vision, and connect teams to tangible business outcomes, goals, and specific releases (22:02)
• Management infrastructure: Quarterly product health reporting and trending metrics (23:20)
• Forming a mental model for company maturity, building a visionary roadmap, and more innovative engineering initiatives (25:34)
• Frameworks for AI Decision-Making: Identifying AI features that drive revenue vs. those that only improve stickiness (31:55)
• Reimagining your product based on different personas, new channels, “AI omniboxes”, and teams / skills of the future (35:44)
• Breaking down team silos, customer engagement as a shared responsibility, and the future of full-stack roles orchestrating outcome-based workflows & automations (41:50)
• Rapid fire questions (45:10)

LINKS AND RESOURCES

• Everything is Tuberculosis by John Green: A historical look at how the disease has shaped the world
• braze.com

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.

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:

• Deconstructing company archetypes: A framework for product-led organizations (2:03)
• Strategic leadership practices for succeeding in product-first cultures (7:33)
• Leveraging data and business metrics to influence product strategy (9:35)
• Case Study: The story and leadership lessons behind building Spotify’s Ad Studio (11:12)
• Rapid prototyping: Applying a hackathon mindset to product development (13:16)
• How AI is reshaping product-led orgs: Clearing the feature backlog, scaling experimentation and velocity (16:01)
• Balancing iteration velocity and product quality with AI (18:12)
• Sebastiano’s observations on effective leadership in business led orgs (19:49)
• Design-led dynamics: Anticipating the impact of AI on creative-first orgs (23:24)
• Maintaining engineering excellence within design-driven constraints (25:40)
• Cultivating high-alignment, valuable design partnerships (27:01)
• The role of metrics and data in design-focused decision making (28:33)
• Emerging AI capabilities enhancing leadership leverage (31:16)
• Scaling management: The potential for 30-50 person teams via AI assistance (33:58)
• The ethical imperative: Adopting AI responsibility within engineering teams (35:53)
• Rapid fire questions (37:12)

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.

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:

• The evolution of Vercel’s all hands to demo days: using live show-and-tell to maintain context and inspire the team (2:4p)
• Accountability for what’s real: Why live visual demos help engineering teams with real-time workflow adjustments (4:36)
• Strategies for creating a successful live visual demo without over-rehearsing (6:20)
• Lindsey’s career inflection point: Navigating the transition from a large ecosystem at Salesforce to a mission-driven startup (10:08)
• Career advice: Vote with your wallet and go somewhere with pre-existing PMF that feeds your ambition (12:33)
• The "Janitor" Mindset: Why prioritizing the company’s mission over a specific job title can lead to unique opportunities (14:36)
• How Lindsey’s open source hobby project led to a code-first interaction with @ Vercel (19:17)
• Vercel’s "Dig Deep" value: Breaking down the company culture and the importance of technical support for developers (21:26)
• Standing out in the interview process: Why managers must bring a strong "Point of View" on what a company should do differently (23:51).
• The Swiss Army Knife Manager: Why today's leaders must also be salespeople, PMs, and customer support engineers (24:46).
• The death of pure "people management": Re-centering on the IC craft and why managers must maintain AI competency (26:12).
• Adopting better IC skills: Building hobby projects for non-technical users to maintain empathy for the user experience (28:33)
• Management principles that remain true today (32:54)
• Combatting imposter syndrome: Building trust by being vulnerable and learning alongside your team (36:45).
• Interviewing trends: Assessing how candidates operate with and without AI tools (38:05).
• The return of "In Real Life" work: Why the Bay Area culture is refocusing on "sweating the details" in person (39:15)
• Rapid fire questions (41:33)

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 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:

• How Chris navigated the transition from Figma to Moonhub (3:47)
• Energy alignment: identifying the mismatch between your role and your drives (6:27)
• Sidesteps aren't inefficiencies: Why it’s okay to not have a specific and/or linear career plan (8:26)
• Building a career “thesis” by balancing passions with industry shifts (11:18)
• The exploration phase: Strategies for a productive four-month “sabbatical” (14:07)
• Leveraging your network and venture capital relationships to understand the market (16:45)
• The utility of “status”: When the “logo” matters & when it’s overrated (19:18)
• The "Running" Framework: Why you shouldn't increase career "speed" and "distance" simultaneously (21:33)
• How Chris applied these ideas to his move from Figma to Moonhub (24:33)
• Avoiding "career injury": Why stretching too thin hinders your flow state (27:07)
• Developing technical depth and leadership in the AI space (29:15)
• Learning through imitation: Finding and emulating leaders five years ahead of you (31:20)
• Chris’s observations on the evolution of technical leadership (34:14)
• The shift from “peacetime” to “wartime” (37:58)
• The "Leaky Abstraction" litmus test: Why leaders must stay in the technical details (39:40)
• Now: Chris’ transition to Agentforce and the future of AI at Salesforce (41:38)
• Rapid fire questions: Growth mindsets and holding identity loosely (43:59)

LINKS AND RESOURCES:

• 99% Invisible: The design and architecture podcast Sulman has followed for over a decade.
• The Invisible Cow Tunnels of Chicago: A specific episode of 99% Invisible mentioned by Patrick.

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.

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!

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SHOW NOTES:

• The Shift to AI-Native Engineering: How AI is collapsing the "Inner Loop" and reshaping engineering team composition (2:48)
• Mission-Driven Teams: Moving from traditional functional silos to integrated, problem-centric units (4:45)
• Vertical vs. Horizontal Team Architecture: How OpenAI structures specialized horizontal teams (ex. Infrastructure, RTC/Voice) with product verticals (7:04)
• Fluid org charts & blurring functional roles: AI-Native teams require proactive mission alignment and coordination over rigid structure (8:48)
• The Lifecycle of Problem-Oriented Teams: What happens when a "strike team" solves the problem (10:02)
• Maximizing cross functional collaboration between engineering, research, product and design (11:52)
• The DRI Framework: Implementing the "Directly Responsible Individual" model for high-velocity accountability (13:32)
• Thriving in the "Chaos Factory": Addressing bottlenecks in highly dynamic, high-volume environments (16:02)
• Prioritization & "Letting 1,000 Flowers Bloom": How OpenAI decides which AI bets to double down on (19:13)
• Scaling Decision-Making: Preventing leadership from becoming the bottleneck as volume increases (21:19)
• Knowing when to call it quits on a bet and reallocate talent for maximum impact (23:29)
• The Manager as "Systems Designer": Shifting the EM role from people logistics to technical orchestration (24:49)
• The Barbell Talent Strategy: Optimizing for innovation by pairing "super seniors" with "super juniors" (28:10)
• Mentorship in the AI Age: How to coaching junior engineers when the "cost of code" is approaching zero (30:19)
• Technical Intuition for Leaders: Sulman’s frameworks for staying "close to the metal" as a manager (33:17)
• Cultivating Judgment: Why "Problem Framing" is the most critical skill for the modern engineer (37:01)
• Rapid fire questions (38:59)

LINKS AND RESOURCES:

• 99% Invisible](https://99percentinvisible.org/): The design and architecture podcast Sulman has followed for over a decade.
• The Invisible Cow Tunnels of Chicago](https://99percentinvisible.org/episode/cow-tunnels/): A specific episode of 99% Invisible mentioned by Patrick.

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.

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!

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Learn more at Retool.com/elc

SHOW NOTES:

• Real-world ROI The Intersection of Bits and Atoms: How Samsara supported customers through a once-in-a-century snowstorm using real-time AI insights (3:59)
• The Practicality Filter: Why low-margin, high-utility businesses are the best "BS detectors" for product builders (9:25)
• Deconstructing the compound product strategy: 10 years of feedback loops, scaling empathy, and technical capabilities (10:53)
• Accelerating your innovation flywheel, customer and product feedback loops (14:39)
• The New Bottleneck: Why writing code is no longer the constraint, and how to optimize for customer absorption of change (19:58)
• The Data Flywheel: Leveraging trillions of proprietary data points to solve new problems and expand your innovation engine into new capabilities (23:36)
• Embedding engineers in customer problems: Why there is no substitute for engineers seeing the frontline environment firsthand (29:56)
• How customer empathy and "taste" amplify the benefits of AI coding agents (33:26)
• Building a system of customer-driven innovation: Utilizing Advisory Boards and "Spark Sessions" to turn 10,000+ customers into co-creators (37:40)
• Rapid fire questions (47:50)

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.