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Hm. The smaller company would be a better choice if you believe in the firm, get some ownership. Would you report to the ceo directly? What tech responsibilities would you have (keep the lights on, or more strategic?). Is there a path from the tech position to more of a line position?
The larger company doesn’t seem to be that much larger (50 vs 100 people?). If it’s much larger say 500 people, it might be a good move as it would offer some advancement opportunity, ability to learn from others etc. What would you specifically be in charge of here? Infrastructure, applications, large projects? I would ask the same questions on reporting struct as above.
In all, you don’t want to be a glorified tech support person.