About this episode

James Cowling discusses his experiences at Dropbox and offers insights on building systems and career advice in the AI era.

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…

People in this episode

Host: Ryan Peterman

Guest: James Cowling

Topics covered

• AI
• career advice
• technical systems
• Dropbox
• software engineering
• simplicity vs complexity

Keywords

• Dropbox
• AI era
• career advice
• technical systems
• simplicity
• complexity
• software engineering

Sponsors

WorkOS

Mentioned in this episode

Organizations: Dropbox, Convex

Products: ergonomic keyboard

More episodes of The Peterman Pod

• Turing Award Winner: P vs NP, Zero-Knowledge Proofs, Quantum Computation | Avi Wigderson · June 1, 2026 · 2h 16m
• Creator of C++: Bell Labs, Negative Overhead Abstraction, Mistakes | Bjarne Stroustrup · May 18, 2026 · 1h 59m
• Harvard Professor: CS50, What Matters More Than CS, Lecturing Well | David J Malan · May 11, 2026 · 1h 4m
• Turing Award Winner: Data Abstraction, Dijkstra, Distributed Systems | Barbara Liskov · April 27, 2026 · 35 min
• Turing Award Winner: Postgres, Disagreeing with Google, Future Problems | Mike Stonebraker · April 20, 2026 · 57 min
• AWS Distinguished Eng: Learning From 3000 Incidents And How Engineering Is Changing | Marc Brooker · April 13, 2026 · 1h 12m

Explore listener stats, chart rankings, contacts and more on the The Peterman Pod podcast page.