Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling

James Cowling is the CTO at Convex and was previously the most senior engineer at Dropbox. We discussed technical details of his past projects, simplicity vs complexity, and career advice given where AI is today.

• My ergonomic keyboard project I mentioned, you can follow along here: read.compose.llc

Podcast links:

• YouTube: youtu.be/3XkmNSuHFmY
• Apple: podcasts.apple.com/us/podcast/the-peterman-pod…
• Transcript: developing.dev/p/dropboxs-former-most-senior-e…

Thank you to this episode's sponsor for supporting my work:

• WorkOS: makes your app Enterprise Ready with easy to use APIs to add SSO, SCIM, RBAC, and more in just a few lines of code, check them out at workos.com

Timestamps:

00:00:00 Intro
00:00:53 Systems work during his PhD
00:13:05 Dropbox technical deep dive
00:21:57 Why Dropbox migrated from AWS
00:36:40 How to do massive migrations
00:44:31 Simplicity vs complexity in promos
00:49:23 What technical teams should be focused on
01:00:25 Doing the right thing vs promo hypothetical
01:08:13 Why he dipped into management sometimes
01:11:36 Why you should not lead by example
01:23:23 How to mentor Senior Staff engineers
01:27:30 Career advice for the AI era
01:37:21 Why he started his own company
01:46:05 The most technically challenging work of his career
01:48:10 How he got involved in Silicon Valley
01:52:16 Career regrets
01:55:54 Top technical book recommendation
01:56:36 Younger self and permanent underclass advice

Where to find James:

• LinkedIn: linkedin.com/in/jcowling
• Twitter/X: x.com/jamesacowling
• His company: convex.dev

Where to find Ryan:

• Newsletter: developing.dev
• X/Twitter: x.com/ryanlpeterman
• LinkedIn: linkedin.com/in/ryanlpeterman
• Threads: threads.com/@ryanlpeterman
• Instagram: instagram.com/ryanlpeterman
• TikTok: tiktok.com/@ryanlpeterman

Referenced in this episode:

• His PhD Thesis: usenix.org/system/files/conference/atc12/atc12…
• Masters paper: cs.princeton.edu/courses/archive/fall19/cos418…
• Papercuts writing he mentioned: medium.com/@jamesacowling/embracing-papercuts-…
• "Don't lead by example": medium.com/@jamesacowling/dont-lead-by-example…
• His writing about orienting teams around missions: medium.com/@jamesacowling/your-system-is-not-a…