A transportation controller (TC) computing system for monitoring a user computing device location and triggering location-based events using geo-fencing is provided. The TC computing system includes at least one TC computing device configured to register a customer with a transportation controller (TC) service using registration data received from a user computing device associated with the customer. The TC computing device is also configured to receive, in response to the user computing device detecting a first geo-fence, first travel data associated with a trip of the customer. The TC computing device is further configured to validate the trip using the first travel data, receive, in response to the user computing device detecting a second geo-fence, second travel data associated with the trip of the customer, and determine a first transaction amount for the trip based on the first travel data and the second travel data.