A work assignment request message, generated by a user device based on input provided by a tow service provider via the user device, is received at an enterprise server device. An initial pool of tow request stocks for potential fulfillment by the tow service provider is selected from a set of pending tow request stocks. A refined pool of tow request stocks is generated to exclude, from the initial pool, tow request stocks for which the tow service provider does not meet at least one fulfillment requirement. An optimized pool of tow request stocks is generated to include one or more tow request stocks selected, according to one or more optimization criteria, from the refined pool of tow request stocks. Information assigning the tow request stocks in the optimized pool of tow request stocks is transmitted from the enterprise server device to the user device.