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.

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.

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.

• 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)

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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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.

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.

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.

• 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)

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.

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.

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.

• 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)

• 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.

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.