Abstract: An illustrative system and method according to the present invention monitors in-the-field meetings of representatives with customers, for example, marketing and sales activity. The system includes a central data system and a portable wireless device (e.g., tablet device, smartphone, etc) deployed with each representative. The portable wireless devices are equipped with a special software application (the “mobile application”) and also a communications device(s) for communicating with the central data system. The portable wireless device provides availability of the representative to the central data system and a guided meeting process, including collection of information, presentation of meeting content, and optional audio recording of the meeting. More particularly, the system can be used for monitoring in-the-field sales of regulated products, such as financial services, including insurance product sales.