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In this paper, we describe multi-itinerary optimization (MIO)--a novel Bing Maps service that automates the process of building itineraries for multiple agents while optimizing their routes to minimize travel time or distance. MIO can be used by organizations with a fleet of vehicles and drivers, mobile salesforce, or a team of personnel in the field, to maximize workforce efficiency. It supports a variety of constraints, such as service time windows, duration, priority, pickup and delivery dependencies, and vehicle capacity. MIO also considers traffic conditions between locations, resulting in algorithmic challenges at multiple levels (e.g., calculating time-dependent travel-time distance matrices at scale and scheduling services for multiple agents). To support an end-to-end cloud service with turnaround times of a few seconds, our algorithm design targets a sweet spot between accuracy and performance. Toward that end, we build a scalable approach based on the ALNS metaheuristic. Our experiments show that accounting for traffic significantly improves solution quality: MIO finds efficient routes that avoid late arrivals, whereas traffic-agnostic approaches result in a 15% increase in the combined travel time and the lateness of an arrival. Furthermore, our approach generates itineraries with substantially higher quality than a cutting-edge heuristic (LKH), with faster running times for large instances. [ABSTRACT FROM AUTHOR]