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: https://read.compose.llc/

Podcast links:

• YouTube: https://youtu.be/3XkmNSuHFmY

• Apple: https://podcasts.apple.com/us/podcast/the-peterman-pod/id1777363835

• Transcript: https://www.developing.dev/p/dropboxs-former-most-senior-eng-building

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 https://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: https://www.linkedin.com/in/jcowling/

• Twitter/X: https://x.com/jamesacowling

• His company: https://www.convex.dev/

Where to find Ryan:

• Newsletter: https://www.developing.dev/

• X/Twitter: https://x.com/ryanlpeterman

• LinkedIn: https://www.linkedin.com/in/ryanlpeterman/

• Threads: https://www.threads.com/@ryanlpeterman

• Instagram: https://www.instagram.com/ryanlpeterman

• TikTok: https://www.tiktok.com/@ryanlpeterman

Referenced in this episode:

• His PhD Thesis: https://www.usenix.org/system/files/conference/atc12/atc12-final118.pdf

• Masters paper: https://www.cs.princeton.edu/courses/archive/fall19/cos418/papers/vr-revisited.pdf

• Papercuts writing he mentioned: https://medium.com/@jamesacowling/embracing-papercuts-e6390055dfc4

• "Don't lead by example": https://medium.com/@jamesacowling/dont-lead-by-example-4f86b1174e64

• His writing about orienting teams around missions: https://medium.com/@jamesacowling/your-system-is-not-a-sports-team-e17f9eb16b94