In road asset management, reactive pavement maintenance is still used in most countries. In this policy, corrective measures are only initiated after clear pavement distress or other deficiencies in road condition have been identified. However, in the philosophy of proactive maintenance, the root causes of damages are always determined before making any corrective measures. In addition, any measures chosen, focus on eliminating or reducing the causes of the problems. The central theme of proactive maintenance is to extend the service life of pavement in accordance with the following principles: 1) the avoidance of unnecessary repairs, 2) damage must never become an acceptable “normal,” and 3) approaching damage is monitored and responded to in a timely manner. In Finland, a pilot towards proactive asset management started in 2015, in cooperation between The Finnish Transport Infrastructure Agency and Roadscanners. The goal of the pilot was to develop and test new innovative methods to improve the productivity of paved roads maintenance. A further aim was to provide new information on the life cycle costs of various roads and the factors that increase these costs. The results of piloting have been promising. The weakest links increasing asset management costs have been identified and maintenance measures addressing the real root causes of the problems have been implemented. As a result, calculated annual paving costs have been reduced already by 20–40%. In addition, valuable information has been collected of the LCC of different maintenance measures. This information is used when moving towards more proactive maintenance policies.