Choosing AI and early-stage startups deliberately

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.

ABOUT CHRIS CHIU

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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SHOW NOTES:

• 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)

LINKS AND RESOURCES:

• 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.

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/

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