What can ancient languages and epic poems teach us about building resilient tech and future-proof teams?

Host Andrew Zigler welcomes Matt Greenwood, Chief Innovation Officer of Two Sigma, for a conversation that uniquely blends their shared background in classical languages with over two decades of Matt’s experience at the forefront of financial technology. Matt unveils how this classical training has profoundly shaped his approach to building enduring innovation, fostering a resilient company culture, and leading with empathy.

Matt explains his vision for building and evolving innovation via platforms, alongside his strategies for effective goal-setting and fostering deep conceptual understanding in his team. He offers invaluable lessons on the importance of forgiving the decisions of our past selves, adapting processes for evolving needs, and thoughtfully engaging with AI to augment human creativity. This conversation is a masterclass in strategic foresight, cultivating a constant hunger for learning, and building an adaptable organization ready for whatever the future holds.

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• Beyond Copilot: What’s Next for AI in Software Development
• Survey: Discover Your AI Collaboration Style

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• Website: twosigma.com
• LinkedIn: Matt Greenwood

Referenced in today's show:

• Google I/O
• Microsoft Build
• Code with Claude
• Java at 30: The Genius Behind the Code That Changed Tech

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What happens when the person trained to spot burnout becomes its next victim?

Kelly Vaughn is a Senior Engineering Manager at Zapier, the author of the After Burnout Substack, and a trained therapist. She joins hosts Ben and Andrew to share her incredibly candid journey of discovering burnout in herself. Kelly reveals how she (despite her professional understanding of burnout's mechanisms) found herself deep in its grip, recounting the slow realizations like dwindling passion, increasing cynicism, and distinct physical tolls like disrupted sleep and a loss of hunger cues.

This raw conversation offers vital lessons for anyone in a high-pressure career (and let’s face it: that’s all of us!). As the tech landscape accelerates with AI, Kelly shares insights on managing its pressures and opportunities. She redefines ambitions for herself alongside the non-negotiables she established for her own well-being when seeking her new role. Listeners will gain powerful insights into identifying their own limits, the courage for pivotal changes, and integrating new demands without self-sacrifice.

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• AI Code Reviews: Automate AI code reviews for every PR
• Survey: Discover Your AI Collaboration Style

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• Personal Website: kvlly.com
• "After Burnout" Newsletter: afterburnout.co
• "The Modern Leader" Newsletter: modernleader.is
• Kelly’s Article: On burnout, quitting, and redefining what matters

Referenced in today's show:

• The FAA has resorted to buying parts on eBay because its equipment is so old, Transportation Secretary Sean Duffy says 
• 2025-05-11 air traffic control
• DOGE Is in Its AI Era
• IRS hopes to replace fired enforcement workers with AI 
• Microsoft lays off about 3% of its workforce in what one executive calls a ‘day with a lo

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Still stuck in a reactive loop with incident response, only fixing problems after they happen? 

JJ Tang, Co-founder and CEO of Rootly, joins host Andrew Zigler to reveal how to shift beyond reactive, leveraging powerful AI and an often-underestimated skill in engineering: genuine customer empathy. Discover how these elements are crucial for navigating the complexities of modern infrastructure and shaping the future of incident management.

JJ explores the forefront of incident response automation, discussing how to integrate shiny new tech like AI safely and why deep customer understanding is key to building trust and reliability. Learn about the common pitfalls leaders face, the cultural shifts needed for proactive reliability, and how teams can make our digital world safer.

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• Beyond Copilot: What’s Next for AI in Software Development
• Survey: Discover Your AI Collaboration Style

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• LinkedIn: JJ Tang
• Website: rootly.com

Referenced in today's show:

• OpenAI agrees to buy Windsurf for about $3 billion, Bloomberg News reports
• Amazon launches first Kuiper internet satellites, taking on Starlink
• Avoiding Skill Atrophy in the Age of AI
• Why developers and their bosses disagree over generative AI

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Is front-end vs. back-end an antiquated way to structure engineering teams? With AI augmenting skills, a new model is emerging: the product engineer.

This week, Andrew sits down with Lee Robinson, VP of Product at Vercel to crack open the future of the web. As a respected educator and voice in the webdev community (check out his YouTube!), Lee shares his unique perspective on building both cutting-edge tools and high-performing teams.

As the VP of Product, Lee charts the evolution of developer roles and illustrates for us the rise of "product engineers" who own features end-to-end. Learn how AI tools are not just augmenting specialists but enabling designers, PMs, and founders to build "personal software." We also cover changing team dynamics and get Lee's advice on navigating the hiring process in the AI era, including: why personalization is key for candidates, how managers can spot authenticity (hint: AI-generated cover letters are obvious!), and why building in public is critical for career growth today.

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• Beyond Copilot: What’s Next for AI in Software Development
• Survey: Discover Your AI Collaboration Style

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• Website: leerob.com
• YouTube: @leerob
• LinkedIn: Lee Robinson
• Vercel: vercel.com
• Next.js: nextjs.org
• v0 by Vercel: v0.dev 

Referenced in today's show:

• This week in social, we noticed: AI
• Duolingo has an AI mandate too
• Google Just Launched an AI-Powered Duolingo Alternative
• Intel CEO announces layoffs, restructuring, $1.5 billion in cost reductions, expanded return to office mandate | Tom's Hardware

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We've spent decades teaching ourselves to communicate with computers via text and clicks. Now, computers are learning to perceive the world like us: through sight and sound. What happens when software needs to sense, interpret, and act in real-time using voice and vision?

This week, Andrew sits down with Russ d'Sa, Co-founder and CEO of LiveKit, whose technology acts as the crucial infrastructure enabling machines to interact using real-time voice and vision, impacting everything from ChatGPT to critical 911 responses.

Explore the transition from text-based protocols to rich, real-time data streams. Russ discusses LiveKit's role in this evolution, the profound implications of AI gaining sensory input, the trajectory from co-pilots to agents, and the unique hurdles engineers face when building for a world beyond simple text transfers.

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• AI Code Reviews: An Engineering Leader’s Survival Guide
• Survey: Discover Your AI Collaboration Style

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• Website: livekit.io
• GitHub: github.com/livekit
• X: x.com/livekit
• Russ: x.com/dsa

Referenced in today's show:

• The Rise of Slopsquatting: How AI Hallucinations Are Fueling a New Class of Supply Chain Attacks
• Has the VSCode C/C++ Extension been blocked?
• OpenAI tells judge it would buy Chrome from Google
• Chain-of-Vibes | Pete Hodgson 
• Seattle crosswalk signals with deepfake Bezos audio may have been hacked with just a cellphone 

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Think building killer APIs like Stripe or Twilio is purely a technical feat? Think again.

This week, we dive into why crafting successful APIs is fundamentally an organizational challenge, demanding internal excellence long before code is deployed. Sagar Batchu, co-founder and CEO of Speakeasy, joins us to unpack the crucial role of ownership, design principles, and why even internal APIs benefit from treating them like first-class products. Discover how Conway's Law dictates your API's fate and why achieving that coveted developer experience starts with your company's structure.

Getting these foundations right is more critical than ever, as the landscape now faces a dramatic shift with the rise of LLMs and agentic AI. This potentially multiplies API usage and introduces the concept of "Agent Experience" (AX), demanding even greater rigor around clear standards, documentation, and metrics like "Time to First 200." Sagar also explores the emerging Model Context Protocol (MCP) and explains why focusing on developer productivity today prepares you for the AI-driven future of tomorrow.

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• AI Features Demo: The Future of Productivity Is AI-Driven
• Survey: Discover Your AI Collaboration Style

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• Website: speakeasy.com
• LinkedIn: Speakeasy
• X: @speakeasydev

Referenced in today's show:

• It costs nothing to be polite unless you're talking to ChatGPT - then it costs tens of millions
• Announcing the Agent2Agent Protocol (A2A) - Google Developers Blog 
• A Deep Dive Into MCP and the Future of AI Tooling

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When it comes to securing software, most developers feel like they're playing catch-up instead of setting the rules.

Tanya Janca (SheHacksPurple), author of "Alice and Bob Learn Secure Coding," brings her 28 years of IT and security expertise—spanning counter-terrorism to enterprise training—to Dev Interrupted. She unpacks the common pitfalls teams face when security is treated as an afterthought, highlighting the developer frustration of being held accountable for security without the tools or knowledge needed to succeed.

Explore how transforming security from a final gate into an ongoing practice saves money, reduces conflict, and builds better software through clear requirements and true developer empowerment. Tanya provides concrete advice for developers and leaders on creating internal knowledge libraries, fostering continuous learning habits, and critically evaluating AI-generated code to ensure it meets security standards. 

Speaking of AI's growing role, we're curious how it's reshaping workflows across the industry. Share your own experiences with AI adoption by taking our quick survey to discover your spot on the adoption graph (and what you can do to level up).

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• Beyond Copilot: Gaining the AI Advantage
• Survey: Discover Your AI Collaboration Style

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• Website: SheHacksPurple
• LinkedIn: Tanya Janca
• Book: Alice and Bob Learn Secure Coding

Referenced in today's show:

• Shopify CEO says staffers need to prove jobs can’t be done by AI before asking for more headcount
• Anthropic flips the script on AI in education: Claude’s Learning Mode makes students do the thinking
• Celebrate 50 years of Microsoft with the company's original source code

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Is your company rushing headlong into AI, only to find it's a 'square peg in a round hole'?

This week, Andrew tackles the critical issue of building trust in AI systems with Brooke Hartley Moy, CEO and co-founder of Infactory.

Brooke, with her experience at companies like Google and Samsung, cuts through the hype and reveals the biggest misconceptions businesses have about AI. We dive into the 'black box' problem, the importance of high-quality data, and why not all AI is created equal.

From seating Matthew McConaughey in the rain to high-stakes medical decisions, we explore the crucial role of domain expertise and the need to move beyond LLM-centric thinking. If you're an engineering leader grappling with AI implementation, this episode is your essential guide to building trustworthy and impactful AI systems.

Check out:

• The Future of Productivity Is AI-Driven

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• infactory.ai
• Brooke Hartley Moy

Referenced in today's show:

• OpenAI declares AI race “over” if training on copyrighted works isn’t fair use
• Exploring Generative AI - Birgitta Böckeler
• AI is "tearing apart" companies, survey finds

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AI is evolving at a breakneck speed, leaving engineering leaders with a critical dilemma: innovate or fall behind. But how do you experiment with AI without risking your credibility? 

Andrew Zigler sits down with Adnan Ijaz, Director of Product Management for Next Gen Developer Experience at AWS, to unpack the power of AI agents. Together they discuss how to leverage autonomous AI in your development workflow, and learn from real-world examples like Amazon Q.

Dive into the evolving role of the developer and discover how to mentor your AI, not just use it. It's time to shift from task-oriented coding to strategic architecture, and this episode shows you how.

But first, co-host Dan Lines frames the conversation by discussing the shift towards measuring the concrete benefits of AI tools in development, rather than just their potential. Dan also provides examples of how to set realistic expectations for AI implementation by focusing on specific tasks and measuring both individual and workflow improvements, highlighting the need for overall workflow optimization.

Check out:

• Translating DevEx to the Board 
• Beyond the DORA Frameworks
• Introducing AI-Powered Code Review with gitStream

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• Adnan Ijaz
• Amazon Q Developer

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Imagine a world where your engineering team ships features at lightning speed, and they're genuinely happy doing it. Sounds like a fantasy? It doesn't have to be. 

This week, we're diving into the secrets of building high-performing, happy engineering teams with Thanos Diacakis, a fractional CTO and engineering coach with over 25 years of experience spanning companies like Uber, where he optimizes software engineering teams and drives technical innovation.

Thanos reveals the common mental models that hold teams back, why 'technical debt' is a myth, and how to break free from the 'feature factory' mindset. Together, he and Andrew explore practical strategies for achieving engineering excellence, from mastering iterations to managing complexity, and discover how to build a culture where velocity and happiness go hand in hand. 

Check out:

• Translating DevEx to the Board 
• Beyond the DORA Frameworks
• Introducing AI-Powered Code Review with gitStream

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Follow today's guest(s):

• Thanos Diacakis
• www.cosmicteacups.com

Referenced in today's show:

• FOSS infrastructure is under attack by AI companies
• Programming is dying. Software development is booming.
• 1 in 3 Americans say they have layoff anxiety

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