This Master's Thesis is built around the concept of fleet management, focusing on designing and implementing a solution for such a purpose. As a target domain for this proposed system snow clearing has been chosen, and it is presented as background for the system realisation. An important feature in a fleet management system is route optimisation. Estimations based on real-world data can be used to construct more effective routes. This optimisation process is not straightforward though, as it belongs in a domain called Vehicle Routing Problems. These problems effectively becomes unsolvable for realisticly sized datasets using traditional optimisation methods, and the reasons behind this and alternative solution approaches are presented in this text. Enhanced fleet monitoring is another target for a fleet management system, and this requires modern localisation technology. To continuously be aware of every unit's position, an accurate tracking mechanism is necessary. Such mechanisms are also presented, focusing mainly on the Global Positioning System (GPS). To create the actual solution, a thorough design phase was necessary. The results of this process, including a requirement specification, a design model and a test plan, are included in this report. Based on the design phase parts of the system have been implemented, such as the graphical user interfaces and communication. The main focus of the implemetation has been on the optimisation process though, and several approaches have been tested. All implentation results, including testing results based on the test plan, can be found in this report. To offer operators a clear view of the positions of the fleet's units, a part of the system will need to work as a geographical information system. This functionality has not been implemented, but its requirements are discussed as well. To add a market perspective to this thesis a business model for a company developing the proposed solution is presented, along with a view on how the solution may affect the business model of companies that implement it into their operations. The last part of the report presents a discussion around the proposed solution. This discussion focuses on the qualities and shortcomings of the solution, how it compares to already existing solutions in the market, and what future work is necessary for the system to be completed.