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.

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.

Bret 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.

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…

• Introduction and Bill Coughran's background at Sequoia and Google (1:36)
• Hiring pitfalls and the biggest mistakes made as a leader (3:49)
• Managing crises: Acting as a dictator during the 2010 Google hack (5:25)
• Building for the AI world without chasing "shiny objects" (7:09)
• Developing context: How to learn AI without relying on LLM summaries (9:02)
• Identifying enduring companies and real value capture in the AI era (10:53)
• The debate on coding assistants and the future of junior engineering talent (13:23)
• Transitions: Making the leap from large organizations to early-stage startups (15:59)
• Staying curious and finding excitement in the next professional challenge (18:23)

• Link to the video for this session
• Link to all ELC Annual 2025 sessions

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/

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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”!

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.

• The "Listening Tour": Grounding leadership in reality and identifying friction points (3:52)
• The Confluence Editor story: Reducing ship time from 120 days to 0 (6:26)
• Moving beyond productivity: Why "Developer Joy" is the metric that matters (8:45)
• Creating a community of Developer Productivity Champions and the power of a Productivity Summit (13:44)
• Elevating productivity to a company-level OKR and measuring qualitative sentiment (17:12)
• Leadership framework: Deciding when to "manage through people" vs. "manage through process" (19:05)
• How to give more direct ownership / responsibility to a DRI (23:03)
• Alignment conversations about prioritizing developer joy & productivity (24:22)
• Challenges faced during Atlassian’s developer joy transformation journey (26:23)
• How the "Developer Joy" foundation enabled building Rovo in just 6 months (30:02)
• The "System of Work": Expanding Jira's utility beyond engineering to finance, marketing, and legal (33:22)
• Rapid Fire Questions (40:48)

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

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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.

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.

• The three core principles of monday.com’s culture: Ownership, Transparency, and Speed of Execution (3:59)
• How AI acts as an accelerant to implement these cultural principles at scale (8:36)
• Why the “Developer” role is evolving into a “Strategic Builder” and “System Designer” (13:47)
• Breaking silos: How the “Builder” role blurs the lines between product, engineering, and design (17:13)
• Real-world example: A designer using AI to submit code and fix UI issues independently (19:09)
• Case Study: The “Agent Factory” & how a weekend prototype by one leader shifted the product roadmap (21:25)
• Operationalizing transparency: Using internal tools (“Big Brain”) to align every builder on daily business impact (25:58)
• The “Kickoff Meeting” framework: A strict protocol for falling in love with the problem, not the solution (32:26)
• The new management paradigm with AI agents as team members (37:31)
• Rapid fire questions (42:09)

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.

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.

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.

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.

• Archetype AI’s mission: Building a foundation model for physical reality (0:24)
• The potential for discovery: Using AI to observe phenomena humans cannot perceive (1:36)
• Augmentation vs. Replacement: Giving humans "superpowers" rather than automating them away (2:48)
• The "Perfect Storm" for Physical AI: Transformers, self-supervised learning, and commodity sensors (4:04)
• Defining “Non-Human Intelligence” and removing the constraints of human labels (6:34)
• Why language is inherently lossy and insufficient for true physical understanding (8:28)
• Real-world application: How Physical AI aids safety decision-making in the solar industry (9:35)
• Use case: Improving pedestrian safety and traffic signaling in Bellevue (12:51)
• The biggest engineering leadership challenge: Embracing the “messiness” of real-world data (14:21)
• Q&A: Why we shouldn't teach AI physical laws, but let it discover them (16:50)
• Q&A: Validating models when there is a defined ground truth vs. subjective language (18:49)
• Q&A: Compute requirements and the future of active learning at the edge (20:05)

• Video version of Jaime and Rashi’s session at ELC Annual 2025

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.

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.

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.

• How leading engineering teams is evolving: Moving from code as the source of truth to specs/documentation as the source of truth (2:44)
• Why an eng org’s good hygiene / health will create better output (5:12)
• A framework for product vision: Envisioning the future "viscerally" like a sci-fi novel, stress-testing assumptions, and focusing smart people on the problem (9:04)
• Hiring in the modern era: Why software engineering is becoming "tooling and data engineering" and the importance of hiring for openness to new research (18:20)
• Gen Z vs. Millennial engineers: Ruslan’s observation that Gen Z is more outcome-oriented and has a lower tolerance for "corporate euphemisms." (22:24)
• Ruslan’s favorite frameworks for effective decision making: Using an "investment deck" to validate projects, avoid disbelief and lack of focus. (25:19)
• Keeping up with the velocity of change: How to curate research inputs and determine when a new paper (like DeepSeek) requires a strategic pivot. (32:57)
• The new burden of leadership: Why the velocity of AI requires leaders to be "right more often" and how to use models to increase research rigor. (36:27)
• The "Data Wall" and Synthetic Data: Why we have hit the wall for text data and how synthetic data generation loops will drive the next wave of defensibility. (41:35)
• The "March of 9s": Analyzing the trajectory of the AI market and why increasing agent reliability is the massive opportunity ahead. (46:25)
• Rapid fire questions (48:18)

• Ruslan’s Talk at ELC Annual 2025
• The War of Art - Steven Pressfield’s guide to inspire and support those who struggle to express their creativity. Pressfield believes that “resistance” is the greatest enemy, and he offers many unique and helpful ways to overcome it.
• A Brief History of Intelligence: Evolution, AI, and the Five Breakthroughs That Made Our Brains - Artificial intelligence entrepreneur Max Bennett chronicles the five “breakthroughs” in the evolution of human intelligence and reveals what brains of the past can tell us about the AI of tomorrow.

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.

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!

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.

• The birth of Brex 3.0: Using a layoff as a "moment to refound the company" (3:38)
• Moving from a Series E to a Series C operational mindset (5:28)
• The problem with a GM model: How siloed OKRs and roadmaps created "deadlock" (6:07)
• New rituals: Why the CEO became "chief editor of the roadmap" (8:16)
• The impact on morale: "Folks just knew how their work fit into the bigger picture" (11:16)
• The challenge of the new model: Who do you hold accountable when you "win and lose as a team"? (13:43)
• The lesson for reintroducing systems: "Less is more" (15:43)
• The "Startup within a Startup": Launching an internal team to disrupt Brex (16:49)
• “What if we were founding Brex again today?” The 4 constraints for the "Hacker House" experiment (17:58)
• Questions eng leaders should ask when running a similar experiment to Brex (21:02)
• Aha moment: "With agentic coating, code is so cheap" (22:35)
• Managing the two narratives: "compounding" the core biz vs. “innovating" with AI (26:01)
• A surprising dynamic: Why the AI team struggled to see their impact (while the core team didn't) (29:38)
• Building alongside your customer to iterate / experiment faster (36:06)
• The turnaround is over: Brex hits 50% YoY growth and cash-flow positive (38:45)
• Rapid fire questions (42:10)

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.