he didn't exactly have the "programmer" look to him, if you know what I mean. He'd be the programmer's boss. The one they hated. The one who made them work on holidays.
The description presents a character who contrasts with the typical image of a programmer. This individual embodies the traits often associated with management, rather than being an actual programmer. He likely has the authority and a formal appearance, which sets him apart from the technical staff who do the actual programming work.
The quote suggests a tension between this boss figure and the programmers, highlighting the common frustrations that arise in workplace dynamics. Programmers may resent managers who impose stressful demands such as working during holidays, illustrating the challenges of balancing leadership responsibilities with understanding the needs of technical teams. The reference to "he didn't exactly have the 'programmer' look" emphasizes this divide further.