In this paper we study the real-time scheduling of time-sensitive full truckload pickup-and-delivery jobs. The problem involves the allocation of jobs to a fixed set of vehicles which might belong to different collaborating transportation agencies. A recently proposed solution methodology for this problem is the use of a multi-agent system where shipper agents offer jobs through sequential auctions and vehicle agents bid on these jobs. In this paper we consider such a system where both the vehicle agents and the shipper agents are using profit maximizing look-ahead strategies. Our main contribution is that we study the interrelation of these strategies and their impact on the system-wide logistical costs. From our simulation results, we conclude that the system-wide logistical costs (i) are always reduced by using the look-ahead strategies instead of a myopic strategy (10–20%) and (ii) the joint effect of two look-ahead strategies is larger than the effect of an individual strategy. To provide an indication of the savings that might be realized under centralized decision making, we benchmark our results against an integer programming approach.