We seek simple conditions on a pair of labeled posets that determine when the difference of their $(P,ω)$-partition enumerators is $F$-positive, i.e., positive in Gessel's fundamental basis. This is a quasisymmetric analogue of the extensively studied problem of finding conditions on a pair of skew shapes that determine when the difference of their skew Schur functions is Schur-positive. We determine necessary conditions and separate sufficient conditions for $F$-positivity, and show that a broad operation for combining posets preserves positivity properties. We conclude with classes of posets for which we have conditions that are both necessary and sufficient.