From Self-Taught Developer to Fractional CTO
On episode 233 of Software Developer's Journey, Oshri Cohen tells Tim Bourguignon how a self-taught engineer worked through every technical role on the way to CTO, and why he chose to go fractional.
Software Developer's Journey
Tim Bourguignon's Software Developer's Journey asks developers how they became who they are. In episode 233 it's Oshri Cohen's turn, and his answer starts without a classroom: he taught himself to code, then learned the rest of the craft by doing the work.
The conversation follows the whole arc. Oshri came up through every technical role a software company has, from developer onward, and each seat shaped how he leads engineering organizations today. Eventually the path reached CTO. Then it kept going, and Tim digs into why Oshri traded the single full-time seat for fractional work across several companies at once.
If you're a self-taught engineer wondering how far the road goes, this episode is the long answer.
What's covered
- How a self-taught developer built a career without the traditional credential
- The path through every technical role on the way to CTO
- Why Oshri left the single full-time seat and went fractional


