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.

 

ABOUT RUSLAN BELKIN

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.

 

SHOW NOTES:

• 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)
•  

LINKS AND RESOURCES

• 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.

 

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.

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!

 

ABOUT JAMES REGGIO

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.

 

SHOW NOTES:

• 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)

 

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 today’s technology landscape, management as a skill is becoming more complex as teams become larger & managers must navigate the balance between relationships and strategic execution. So how can AI tools help managers level up their game? Jonathan Raymond (Founder & CEO @ Ren) shares insights that can help managers navigate their modern-day invisible cognitive loads. We cover how AI can be used to enhance – not replace – inherently human skillsets, the three components that make up an effective manager / employee relationship, product-building principles for building relational systems, and using AI to guide rather than provide concrete answers.

 

ABOUT JONATHAN RAYMOND

Jonathan Raymond is the Founder and CEO of Ren, an AI agent for managers and teams that helps them give and receive feedback, have meaningful 1:1s, and access real-time personalized coaching. He is also the author of the award-winning book Good Authority and was named one of Inc. Magazine’s Top 100 Leadership Speakers. Previously the CEO of EMyth, Jonathan has led transformation projects across technology, renewable energy, and coaching. He’s a half-decent barista, a mediocre-but-enthusiastic surfer, and will never give up on the New York Knicks.

SHOW NOTES:

• Jonathan’s perspective on the impossible cognitive load & colliding pressures of modern managers (2:31)
• The complicated workflow it takes to be a great manager (6:05)
• “Field Intelligence” and the need to ingest non-technical data such as (mood, sentiment, and alignment) to make better leadership decisions (9:52)
• The managerial matrix: high/low performers and the 10-person team that feels like 50 (12:46)
• The cost of mismanaging your team & why it’s so easy to get it wrong (16:02)
• What’s uniquely human vs. where AI provides leverage (18:01)
• AI’s role: detecting signal and prompting human reflection (21:04)
• The “Growth Loop”: a 3-part system for effective leadership (27:20)
• Incorporating AI tools to enhance the manager / employee relationship (31:20)
• The future vision: an “in-ear” AI coach that closes the gap between learning and applying (33:09)
• Closing the gap between learning a new skill & it becoming an unconscious habit (35:59)
• Product Principle: Building a “Relational System,” not just a task manager (37:49)
• Product Principle: Why an AI coach must ask questions, not provide answers (40:50)
• How to harness AI tools for better emotional articulation / processing (45:11)
• A simple behavioral change to try this week (47:58)
• Rapid fire questions (49:57)

LINKS AND RESOURCES

• Good Authority: How to Become the Leader Your Team is Waiting For - Jonathan’s book in which he brings together what he has learned over a twenty-year journey as an executive, entrepreneur, team leader and leadership trainer.
• Entangled Life: How Fungi Make Our Worlds, Change Our Minds & Shape Our Futures - Merlin Sheldrake explores the spectacular and neglected world of fungi: endlessly surprising organisms that sustain nearly all living systems.
• Jonathan’s session at ELC Annual 2025

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.

Businesses are spending millions on AI tools hoping to accelerate time-to-market but aren't seeing organizational-level results. Laura Tacho (CTO @ DX) explains why an "individual productivity" mindset fails and how AI merely accelerates the condition of the system it enters. She provides a framework for leaders to shift to a systems-level approach, find high-leverage ROI by looking outside the 20% of time spent coding, and understand what sets high-ROI orgs apart. Plus Laura shares data literacy tools to cut through the "whiplash" of conflicting AI reports and provides key considerations for 2026 budgeting, detailing where and how companies are planning to strategically invest.

ABOUT LAURA TACHO

Laura Tacho is CTO at DX, a developer experience company. She previously led teams at companies like CloudBees, Aula Education, and Nova Credit. She’s an expert in building world-class engineering organisations that consistently deliver outstanding results. Laura has coached CTOs and other engineering leaders from startups to the Fortune 500, and also facilitates a popular course on metrics and engineering team performance.

SHOW NOTES:

• Downsides to approaching organizational outcomes from an individual task level (2:59)
• Why individual product gains don’t always equate to systems-level improvements (4:56)
• How the quality of existing systems impacts the improvements AI can foster (7:26)
• Strategies for shifting mental models from the individual to systems level (9:09)
• Implement training & enablement techniques as an organizational lever (11:22)
• Common workflows that can unlock new problem-solving methods (14:46)
• Understanding what impact you want to see / getting the most ROI from AI (18:40)
• How to interpret the data when it comes to AI & its true ROI (21:22)
• AI data literacy for engineering leaders (23:06)
• Interpreting the meter study & what it means for engineers using AI (25:49)
• Quality vs. quantity when it comes to AI implementation on the org level (28:43)
• Characteristics that high-ROI companies possess when it comes to AI (30:35)
• Strategies to invest in that may lead to higher ROI (32:29)
• Laura’s observations on time & money budgeting / investments for 2026 (35:28)
• Embracing cost savings & opportunity generation as an eng org (38:08)
• Tackling fear / uncertainty when it comes to AI adoption, budgeting, & ROI (40:01)

LINKS AND RESOURCES

• Previous Episode with Laura Tacho
• Introducing the AI Measurement Framework from DX
• Atlassian State of DevEx Report
• METR Study
• DORA Report (2025)

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.

What happens to platform engineering when natural language becomes the primary interface to infrastructure? Miriam Aguirre (Co-founder & CEO @ Ingenimax) joins us to explore how AI is fundamentally reshaping platform strategy, team structures, and the very role of the platform engineer. We deconstruct the shift from tactical "how" to strategic "why" and explore what it means to lead and build resilient systems in this new paradigm.

ABOUT MIRIAM AGUIRRE

Miriam Aguirre is the Co-Founder and CEO of Ingenimax, the company behind StarOps, an AI-powered platform engineering engine that helps teams deploy and manage kubernetes and other cloud-native systems in minutes, not months. Before Ingenimax, Miriam served as CTO and engineering leader at two startups that successfully scaled from early stage through IPO. Her career spans deep expertise in high-throughput, scalable systems and machine learning, with a focus on building the technical and organizational foundations for hypergrowth. Miriam is passionate about engineering leadership that turns complex technology into intuitive, reliable platforms, and about helping teams scale without losing their soul.

 

ToolHive Unlocks the Full Value of MCP & Your AI Agents

So you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.

ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).

ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.

Leaders trust ToolHive to put MCP into production and put their AI agents to work.

ToolHive is open source, so get started for free at toolhive.dev

 

SHOW NOTES:

• The Origin Story of Ingenimax (3:05)
• The recurring scaling problem: Why "scaling teams" means scaling systems first (5:23)
• How the age of AI forces platform strategy to evolve earlier in a company’s journey (8:48)
• The decline of vendor lock-in and the rising appetite for experimentation with tech (10:56)
• The paradigm shift that breaks the old model: natural language as the new interface (14:11)
• Why deep knowledge of fundamentals is now more important than syntax (16:56)
• Shifting requirements conversations from tactical inputs to strategic outcomes (20:22)
• Balancing standardization and flexibility with guardrails in an AI-driven environment (22:58)
• The challenge of getting from an AI prototype to a polished product (26:42)
• How platform team roles will evolve to focus more on curation (29:32)
• How to become a great technology curator (37:30)
• Rapid Fire Questions (39:56)

LINKS AND RESOURCES

• The Book of George - From the author of the critically acclaimed Laura & Emma comes a The Love Affairs of Nathaniel P. for our times: Kate Greathead's razor-sharp but big-hearted excavation of millennial masculinity.
• Can Animals and Machines Be Persons?: A Dialogue - This is a dialogue about the notion of a person, of an entity that thinks and feels and acts, that counts and is accountable. Equivalently, it's about the intentional idiom --the well-knit fabric of terms that we use to characterize persons. Human beings are usually persons (a brain-dead human might be considered a human but not a person). However, there may be persons, in various senses, that are not human beings. Much recent discussion has focused on hypothetical computer-robots and on actual nonhuman great apes. The discussion here is naturalistic, which is to say that count and accountability are, at least initially, presumed to be naturally well-knit with the possession of a cognitive and affective 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.

In this episode, we’re addressing one of the biggest challenges current eng leaders are facing – balancing yesterday’s constraints with tomorrow’s potential! Chrystal Henke Ball (VP of Engineering @ Yahoo) shares insights on why it’s important to constantly challenge your assumptions and how vision can sometimes work as a bottleneck for your organization. We dissect how the traditional product lifecycle is evolving to become more fluid and what that means for the collaborative relationship between product, eng, and design. Additionally, Chrystal defines grit, why it’s important for leaders to model it, and strategies for cultivating the trait within your eng team in order to move past short-term challenges and focus on long-term goals!

 

ABOUT CHRYSTAL HENKE BALL

Chrystal Henke Ball a seasoned engineering leader, currently serving as VP of Engineering at Yahoo, where she leverages her experience to accelerate product development across core products such as Yahoo.com and the Yahoo News app. Prior to Yahoo, she led engineering organizations at Google Search, Pandora, Pachama, and Arcadis, building highly available systems, guiding architectural transitions, spearheading novel solutions, and delivering delightful user experiences. Chrystal excels at designing purpose-driven, scalable architectures, streamlining development processes, and mentoring teams to work effectively and openly together.

 

ToolHive Unlocks the Full Value of MCP & Your AI Agents

So you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.

ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).

ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.

Leaders trust ToolHive to put MCP into production and put their AI agents to work.

ToolHive is open source, so get started for free at toolhive.dev

 

SHOW NOTES:

• Navigating the challenge of balancing constraint vs. innovation (3:05)
• Considerations for balancing current capabilities w/ your roadmap to change (4:34)
• Frameworks for categorizing what’s fixed vs. in flux to aid decision-making (6:14)
• Conversation points for checking your assumptions (7:36)
• The new leadership challenge: vision as a bottleneck (14:45)
• Evolving feedback loops to address a more fluid product lifecycle (19:43)
• Defining product vision in today’s fast-paced, fluid landscape (23:57)
• Defining grit as an essential trait & ways to cultivate it as an eng leader (31:57)
• Building AI-incorporated products with trust as a foundational principle (40:46)
• Rapid fire questions (43:01)

 

LINKS AND RESOURCES

• Talking to Strangers: What We Should Know About the People We Don't Know - Malcolm Gladwell, host of the podcast Revisionist History and author of the #1 New York Times bestseller Outliers, offers a powerful examination of our interactions with strangers -- and why they often go wrong.
• Terrestrials - A show for people of all ages that explores the strangeness that exists right here on Earth. In each episode, host Lulu Miller (co-host of Radiolab) will introduce you to a creature or earthly phenomenon that will defy your expectations of how nature is supposed to work. Along the way, you'll encounter a chorus of experts, including scientists, surfers, hip hop artists and…a "Songbud" named Alan (indie punk musician Alan Goffinski) who creates original songs for key moments of confusion, discovery or awe. New episodes drop Thursdays. Listen in with your whole family. Or all alone.

 

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.

How do you apply your leadership skills to a new, mission-driven industry and effectively lead teams across multiple technical domains? In this episode, Simone Kalmakis (VPE @ Viam) shares her playbook for successfully transitioning between industries from health-tech and climate to her current work in robotics and AI. We deconstruct the leadership models she uses to prioritize her time, manage multiple technical experts, and why she focuses on "depth with 1-2 teams > breadth". Plus, her framework for onboarding in a new domain, the lifecycle of a leadership "deep dive," and communication practices that build trust and empower your entire organization to stay aligned and motivated.

ABOUT SIMONE KALMAKIS

Simone Kalmakis is the VP of Engineering at Viam, a platform unlocking AI, data, and automation for devices in the physical world. She has deep experience applying AI and machine learning to big data and big missions, and is known for building healthy engineering organizations that drive business value and real-world progress.

Prior to Viam, Simone was Senior Director of Engineering at Arcadia, a climate tech company building an API platform for residential utility data to power solutions that fight climate change. Before that, she served as Director of Engineering at Flatiron Health, where she helped accelerate the development of cancer treatments through real-world data.

Simone began her career at Microsoft, developing machine-learned relevance algorithms for Bing. She’s also a successful founder––after Microsoft, she built and sold Symbi, a roommate-matching startup. She holds a degree in Mathematics and Economics from Yale University.

 

ToolHive Unlocks the Full Value of MCP & Your AI Agents

So you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.

ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).

ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.

Leaders trust ToolHive to put MCP into production and put their AI agents to work.

ToolHive is open source, so get started for free at toolhive.dev

 

Join us at ELC Annual 2025

ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!

🔗 Get your ticket now → https://sfelc.com/annual2025

 

SHOW NOTES:

• Simone’s eng leadership journey from health-tech to climate to robotics (3:25)
• Lessons from being a founder & how it led to Viam (5:27)
• Co-founding lessons that Simone continues to apply (7:22)
• Navigating the transition from Flatiron Health to Arcadia (9:20)
• Transitioning from Arcadia to Viam (12:06)
• Use cases of physical devices impacting the environment through data / AI (14:28)
• How Simone sees Viam potentially working in a day-to-day capacity (15:42)
• How to structure your time when entering a new industry (17:51)
• Onboarding with a personal project to build user empathy, alignment & motivation (20:34)
• Finding where your expertise is the highest-leverage for your org (22:34)
• “The goal is not to maintain the same level of depth in each of your teams” (24:18)
• How to decide which teams get your deep focus (27:15)
• Building trust through transparent communication about your priorities (29:19)
• The lifecycle of a leadership “deep dive” from start to exit (32:20)
• Advice for leaders adopting this hands-on, flexible approach (36:15)
• Key questions to ask when seeking a more mission-aligned industry (38:01)
• Rapid fire questions (40:33)

LINKS AND RESOURCES

• Viam - a full-stack solution for the kinds of devices that exist anywhere from your home, your office, in cars or boats, in warehouses or factories, at arenas, or other public places.

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.

"If we were building Box today, what would we do?” Ben Kus (CTO @ Box) deconstructs their playbook for enterprise AI innovation. We cover their journey to reimagine & reorient the company to a new technical vision, how they run a “multi-speed” org that balances startup agility and & enterprise-grade stability, and their “platform first” approach to build AI features. Ben also explains why security/compliance was foundational from "day negative one" in their AI strategy, the evolution of agentic AI, determining the right guardrails for AI agents & the future of multi-agent systems, enterprise trends & more.

 

ABOUT BEN KUS

Ben Kus is the Chief Technology Officer at Box, where he leads technology and AI strategy to help enterprises securely unlock insights from their unstructured data. Ben’s career spans engineering, product leadership, and startup innovation—including co-founding Subspace (acquired by Box) and being an early employee at BigFix (acquired by IBM), where he later served as Chief Architect of Mobile Security. Ben holds a degree in Computer Science from UC Berkeley.

 

ToolHive Unlocks the Full Value of MCP & Your AI Agents

So you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.

ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).

ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.

Leaders trust ToolHive to put MCP into production and put their AI agents to work.

ToolHive is open source, so get started for free at toolhive.dev

 

Join us at ELC Annual 2025

ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!

🔗 Get your ticket now → https://sfelc.com/annual2025

 

SHOW NOTES:

• How Generative AI sparked Box’s reoriented vision, by unlocking the value of unstructured data (3:29)
• Using GenAI to create structure out of unstructured data (5:28)
• Internal & external conversations that inspired Box’s new direction (7:18)
• Box’s “platform first” approach to building a secure and scalable foundation for all future AI features (10:02)
• Why security and compliance must be built in from "day negative one" not added on later (12:40)
• How to set a technical vision that can respond to future developments you can't yet predict (14:46)
• The “multi-speed” business model: Using a small, fast-moving internal group to test ideas before they enter the normal, slower development cycle (17:47)
• Example of a successful project: AI-driven data extraction & the evolution to critical feature (20:26)
• The story of an abandoned project and the challenge of knowing which ideas are revolutionary versus which aren’t worth continuing (22:17)
• Ben’s long-term vision for AI agents and why he believes they are an incredibly powerful technology paradigm (23:58)
• State diagrams & the journey behind building Box’s initial agentic AI systems (26:50)
• “Context Engineering”: The new paradigm of programming and the mental model shift required for engineers to adopt it (29:07)
• The future of AI benchmarks: Measuring what a person can accomplish with an agent, not just the agent’s performance alone (31:03)
• How to balance development speed with security risks, especially when agents can take actions and change the environment (34:00)
• Key questions to ask to determine the right guardrails for AI agents, including thinking about the worst-case scenario (36:41)
• Enterprise technology trends to watch, and why multi-agent systems will become the new “org chart” (37:56)
• Rapid fire questions (39:03)

LINKS AND RESOURCES

• Harry Potter and the Methods of Rationality - Eliezer Yudkowsky’s alternate-universe Harry Potter fan-fiction wherein Petunia Evans has married an Oxford biochemistry professor and young genius Harry grows up fascinated by science and science fiction. When he finds out that he is a wizard, he tries to apply scientific principles to his study of magic, with sometimes surprising results.

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.

Engineering leadership is undergoing a seismic shift, requiring playbooks to be rewritten, in real-time. In this special episode, hosts Patrick Gallagher and Jerry Li give you an inside look at the ELC Annual 2025 experience, and how the two-day conference will equip you with new mental models, skills, and frameworks required to lead.

Get a preview of tactical takeaways from deep operational dives into companies like OpenAI, Amplitude, and HeyGen. Discover how the conference will help you redesign your innovation engine, transform your team's workflows, and blur the lines between engineering, product, and business to drive impactful change. Through a unique mix of tactical sessions, peer-led roundtables, and curated mentorship, you'll learn how to find the community and coaching needed to lead through uncertainty and invest in your own career growth.

To learn more & get tickets, go to sfelc.com/annual2025

Use code podcast15 for 15% off tickets - group tickets / discounts available.

 

ABOUT ELC ANNUAL

The playbook for engineering leadership is being rewritten. ELC Annual 2025, happening September 10-11 in San Francisco, is where you'll gain the insights, strategies, and deep connections needed to lead in this new era. 50+ speakers, 50+ peer-led roundtables discussions, 1:1 matching to expand your network. Insights, connections & support.

Join the community of engineering leaders who are co-creating the future of our field.

Listener Discount → Use code podcast15 for 15% off

Group Tix → For teams looking to attend together, special group discounts can be found under the 'Tickets' section of our website!

Secure your ticket at sfelc.com/annual2025

 

ToolHive Unlocks the Full Value of MCP & Your AI Agents

So you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.

ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).

ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.

Leaders trust ToolHive to put MCP into production and put their AI agents to work.

ToolHive is open source, so get started for free at toolhive.dev

 

Join us at ELC Annual 2025

ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!

🔗 Get your ticket now → https://sfelc.com/annual2025

 

SHOW NOTES:

• The ground is shifting: Why the old playbooks for engineering leaders are being rewritten (0:55)
• Moving beyond AI hype to harnessing its real power in your products and workflows (2:44)
• How are teams & workflows changing? Redefining roles and upskilling your team for the AI era (9:06)
• Why the smartest insights don't come from the stage, but from deep, honest conversations with peers in roundtables (13:36)
• How curated one-on-one matches help you build a trusted network to rely on for years to come (16:08)
• ELC Annual isn't a tech conference; it's a career conference to invest in yourself and your leaders (17:49)

 

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.

What if your engineering team didn’t just write code, but owned product discovery, wrote the launch messaging, and handled early sales? In this episode, Michael Grinich, CEO and founder of WorkOS, deconstructs their playbook for collapsing the product/engineering stack: no design leads, only one PM, and engineers who own product end-to-end. Michael breaks down how they teach product thinking, build with deep customer insight, and why his most important job is often to "cut scope." You’ll learn how to remove the "lossy translation layers" between teams, build a culture of curiosity and customer obsession, and ship higher-quality products, faster.

ABOUT MICHAEL GRINICH

Michael is the founder and CEO of WorkOS, a developer platform that enables companies to become Enterprise Ready through features like Single Sign-On (SAML). Their customers include many of the fastest-growing startups including Webflow, Drata, Loom, and +200 others. Before WorkOS, Michael co-founded Nylas and studied CS at MIT.

 

ToolHive Unlocks the Full Value of MCP & Your AI Agents

So you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems.

ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP).

ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe.

Leaders trust ToolHive to put MCP into production and put their AI agents to work.

ToolHive is open source, so get started for free at toolhive.dev

 

Join us at ELC Annual 2025

ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections!

🔗 Get your ticket now → https://sfelc.com/annual2025

 

SHOW NOTES:

• Marketing technical products exclusively to other tech companies (2:39)
• Building products end-to-end without PMs (6:36)
• How WorkOS utilizes fun, user feedback, and cohesive storytelling in their product-building process (9:31)
• Hiring engineers for curiosity & comfort operating in ambiguity (12:48)
• How engineers owning product discovery & directly engaging w/ users improve product insights (16:31)
• Using Slack for real-time integrated support & rapid product iteration (19:38)
• The complexities of creating simple, elegant products and marketing messaging (21:54)
• Cut scope ruthlessly to ship faster and better (26:20)
• Small, simple, deeply useful features make the biggest impact (30:30)
• The weekly cadence that keeps engineering aligned (32:52)
• Behind the scenes of MCP Night: A protocol party for devs (38:20)
• Rapid fire questions (41:29)

LINKS AND RESOURCES

• MCP Night
• **WorkOS Launch Week**
• WorkOS AuthKit
• The Business Value of Computers: An Executive's Guide - Paul A. Strassmann addresses the practical needs of executives responsible for planning, budgeting and justifying information technology expenditures. It shows that there is no direct relation between spending on computers, profits or productivity.

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.