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NEW - EPISODE 234

A Systems-Level Guide to High-ROI AI Impact

with Laura Tacho


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.
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On this show, we uncover stories and examples of great leadership in software engineering, explore the experiences of industry leaders, as well as share actionable insights from leadership and management thought experts artful and skilled in the application of leadership.
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FEATURED STORY
Oct 21, 2025

Platform Engineering's Shift from Tactical 'How' to Strategic Curator & Natural Language as the New Interface Paradigm

with Miriam Aguirre

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.
FEATURED STORY
Oct 15, 2025

Grit, the vision bottleneck & building for a future where today’s technical constraints may disappear

with Chrystal Henke Ball

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!
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Sept 1, 2020
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LATEST

Episode 234: A Systems-Level Guide to High-ROI AI Impact

with Laura Tacho

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.
Oct 28, 2025

Episode 233: Platform Engineering's Shift from Tactical 'How' to Strategic Curator & Natural Language as the New Interface Paradigm

with Miriam Aguirre

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.
Oct 21, 2025

Episode 232: Grit, the vision bottleneck & building for a future where today’s technical constraints may disappear

with Chrystal Henke Ball

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!
Oct 15, 2025

Episode 231: Leading across technical domains, strategic deep-dives & applying your skills in new industries

with Simone Kalmakis

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.
Sep 09, 2025

Episode 230: How Box Builds AI Agents, Redefines Technical Vision, and Balances Speed with Security

with Ben Kus

"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. 
Aug 26, 2025

Episode 228: The End-to-End Engineer: How Workos Collapsed the Talent Stack for High-Velocity Execution, Ownership & Better Product Decisions

with Michael Grinich

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.
Aug 05, 2025

Episode 227: Influencing without authority: What every engineering leader can learn from security

with Srinath Kuruvadi

Influencing without authority is the hidden superpower of security leadership—and a crucial skill every engineering leader must master. In this episode, Srinath Kuruvadi (Head of Cloud Security @ JPMorgan Chase) breaks down how to influence without formal authority and advocate when ROI isn’t immediately clear. We cover tactics for shaping problems from the POV of other stakeholders, Plus, strategies to establish shared outcomes, insights on optimizing your time, emerging AI x security trends, and how his team is operationalizing curiosity & experimentation through The Innovation Lab.
Jul 22, 2025

Episode 226: Vision-first leadership & reimagining product w/ “Shift Out,” Do-It-as-a-Service & Jobs-to-Be-Done

with John Amaral

John Amaral (CTO and co-founder @ Root.io) joins us to discuss the evolving role of engineering leaders and why vision-first leadership & building your “vision” muscle is more critical than ever. We dive into why “shift left” is dead and why SaaS is being replaced by “do-it” as a service. John also unpacks how to think in outcomes, apply the Jobs-To-Be-Done framework to eliminate toil, and reimagine product experiences. Plus, we look inside Root.io’s approach to building AI-native security products that ship daily. Whether you’re rethinking your org design or exploring the frontier of AI-powered engineering, this episode will reshape how you think about building, leading, and scaling teams.
Jul 08, 2025

Episode 225: Scaling decision-making, designing eng orgs for speed & scope as underrated leverage

with Dhruv Parthasarathy

What does it take to operate with startup-level speed… in one of the most complex, high-stakes industries on the planet? In this episode, we go inside Commure’s engineering org w/ Dhruv Parthasarathy (CTO @ Commure & Athelas). We cover how to push decision-making down to move faster and reduce risk, structure teams for rapid iteration, and turn customers into product co-creators. Dhruv also shares how they cultivate polymath capabilities across EPD to accelerate velocity, why scope is one of the most underrated sources of leverage in engineering, and the frameworks they use to identify compound wins. If you’re scaling an eng org, leading in a complex domain, or designing your team for speed—this episode is packed with tactical frameworks you can apply immediately.
Jun 25, 2025

Episode 224: The evolving velocity playbook, building product taste & exceptional product experiences in the AI era

with Loïc Houssier

How do you lead a high-velocity engineering team—when everything about how we build is changing? How do you cultivate more of a product mindset in your engineering teams? Loïc Houssier (VP Engineering @ Superhuman) shares his evolving playbook for driving velocity in eng orgs today, building product-minded teams, and cultivating product taste. We cover leading culture / mindset transformation, creating exceptional product experiences, operational excellence when product quality is increasingly subjective. Plus the evolution of productivity tools!
Jun 17, 2025
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