Career Inflection: Leaving Salesforce for Startups

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.

ABOUT LINDSEY SIMON

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.

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SHOW NOTES:

• 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)

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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