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.

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• 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/

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Kiren Sekar (CPO @ Samsara) joins us to deconstruct the "Innovation Engine" behind Samsara, and how this system drives real-world impact and ROI across their products. We explore Samsara’s decade-long compound product strategy and the mechanics of accelerating feedback loops in an era where the primary bottlenecks shift from code generation to customer feedback and absorption of change. Kiren details how their data flywheel expands the aperture of what is possible to build and we dive into the system of customer-driven innovation: advisory boards, “spark sessions” to test hypotheses and gain unfiltered feedback. Plus we talk about the power of embedding engineers in frontline environments (from truckyards to construction sites) to cultivate “taste,” customer empathy and trigger non-linear ideas.

Kiren Sekar is the Chief Product Officer at Samsara (NYSE: IOT), where he has helped lead the company from a hardware-hacking startup in a basement to a global leader in Connected Operations with over $1.5B in ARR. An early leader at Meraki (acquired by Cisco for $1.2B) and an Apple veteran with multiple patents, Kiren specializes in the rare intersection of hardware, massive-scale data, and AI. He is the architect of a platform that now processes trillions of data points for the industries that keep the world running—trucking, construction, and logistics.

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• Real-world ROI The Intersection of Bits and Atoms: How Samsara supported customers through a once-in-a-century snowstorm using real-time AI insights (3:59)
• The Practicality Filter: Why low-margin, high-utility businesses are the best "BS detectors" for product builders (9:25)
• Deconstructing the compound product strategy: 10 years of feedback loops, scaling empathy, and technical capabilities (10:53)
• Accelerating your innovation flywheel, customer and product feedback loops (14:39)
• The New Bottleneck: Why writing code is no longer the constraint, and how to optimize for customer absorption of change (19:58)
• The Data Flywheel: Leveraging trillions of proprietary data points to solve new problems and expand your innovation engine into new capabilities (23:36)
• Embedding engineers in customer problems: Why there is no substitute for engineers seeing the frontline environment firsthand (29:56)
• How customer empathy and "taste" amplify the benefits of AI coding agents (33:26)
• Building a system of customer-driven innovation: Utilizing Advisory Boards and "Spark Sessions" to turn 10,000+ customers into co-creators (37:40)
• Rapid fire questions (47:50)

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.