Heat the oil in a medium pot set over medium-high heat. Add the sausage and cook, breaking it up into very small pieces with a wooden spoon, until well browned and cooked through, 5 to 7 minutes. Drain off any excess grease. Reduce the heat to medium, and add the tomatoes. Simmer, breaking the tomatoes up with the spoon, until softened and slightly reduced, 3 to 5 minutes. Add the cream cheese. Stir until the cream cheese melts and the mixture is combined. Season generously with salt and pepper. Adjust the consistency with up to 1/4 cup of water if the dip is too thick; it should be the consistency of thick cream but not as thick as pudding. Serve warm with chips for dipping.
Adapted from Mimi's Sausage Dip from The Player's Retreat for Cooking Channel