1. An information processing system comprising: an information processing apparatus; and a vehicle-mounted device that is mounted in a vehicle, wherein the vehicle-mounted device comprises: a sound pickup unit that picks up a speech sound, and a transmitting unit that transmits speech data that is generated based on the speech sound that is picked up by the sound pickup unit to the information processing apparatus; and the information processing apparatus comprises: a storage unit which stores pictogram correspondence information in which keywords and pictogram information indicating a plurality of pictograms which correspond to the keyword are associated, and a control unit that executes pictogram selection processing which selects the keyword corresponding to text representing a speech sound that is generated by speech recognition based on the speech data from among the keywords which the pictogram correspondence information includes, and in accordance with a predetermined condition, selects one item of the pictogram information from among a plurality of items of the pictogram information that are associated with the keyword that is selected.