Ok, since we're talking software pirates here, not real pirates (otherwise the outcome would be obvious) who wins in an average matchup?
Software pirate - Probably very pale and skinny due to skipping meals and time outside in order hack or organize pirated playlists. Resulting low vitamin intake can affect durability. Small target. Hyped up on caffeine. +5 to defense, +7 to speed, -10 to HP, -4 to strength. Levels up 20% faster due to time spent playing Fight Night on modded Xbox.
Software designer - Tends to be larger due to snacking on the job. Caffeine adds no bonus (addicted). Large mass can offer several advantages. -4 to defense, -10 to speed, +10 to HP, +6 to strength. Can invoke Putrid Socks of Nonwashing.