How to Plan Software under Uncertainty 🗺️ - by Luca Rossi

Hey there! A couple of weeks ago I sat down for a chat with James Cowling, CTO at Convex and former Senior Principal Engineer at Dropbox. James’ work at Convex is incredible and I encourage you to check it out, while his track record at Dropbox is equally impressive. There, he led some of the company’s most daunting projects, including designing a multi-exabyte storage system, and later migrating it from AWS to in-house infra. These were enormous, multi-year projects, so, our chat naturally gravitated towards the challenges of leading them. In particular, I was interested in how you plan and execute these right. In fact, not only are these projects massive — they also happened in a hyper-growth context, where assumptions shift all the time, and the team doubles in size year over year. It was an incredible conversation. So, this week I took all the notes from the interview, combined them with my own ideas, and created this special edition. Other than the full video of James’ interview,

Hey there! A couple of weeks ago I sat down for a chat with James Cowling, CTO at Convex and former Senior Principal Engineer at Dropbox. James’ work at Convex is incredible and I encourage you to check it out, while his track record at Dropbox is equally impressive. There, he led some of the company’s most daunting projects, including designing a multi-exabyte storage system, and later migrating it from AWS to in-house infra. These were enormous, multi-year projects, so, our chat naturally gravitated towards the challenges of leading them. In particular, I was interested in how you plan and e