A lot of his best insights required technical knowledge - adopting Ethernet, SCSI, Mach kernels, BSD userland, object oriented programming, Postscript, TrueType fonts, WebObjects (and Java server, while ditching it on the client), html5 (over Flash)
Even then it would be 'known unknowns' to him as compared 'unknown unknowns'. It is big deal considering we just saw Marissa Meyer who was at center of creation of a web scale system proved out of depth at slightly different web scale system.