Using the fact that $\Omega^1$ is $\mathcal{O}_X$-locally free and dual to the sheaf of vector fields you should be able to prove $Hom_{\mathcal{O}_X}(\Theta_X,\mathcal{E}nd_\mathbb{C}(V)) = Hom_\mathbb{C}(V,V\otimes_{\mathcal{O}_X} \Omega^1)$. In local complex coordinates $(x_1,\ldots,x_n)$, $\\{\
abla_Y\\}$ is mapped to $\
abla: V \to V\otimes \Omega^1$ defined by $$ \
abla(v) = \sum_{i=1}^n \
abla_{\partial_i}(v) \otimes dx_i $$ (This the analogue of $df = \sum_i \frac{\partial f}{\partial x_i} dx_i$). Condition (2) ensures that this formula does not depend on the choice of coordinates.