This research analyses six key traveller jobs, scoring their current performance. Travellers struggle with information overload (4/10), evolving initial ideas (2/10), group alignment (1/10), balancing exploration with reliability (3/10), confirming practical viability (6/10), and designing itineraries (1/10). Key pain points include fragmented information, manual coordination, and difficulty optimising for group preferences. These challenges present an opportunity for Taash to connect venues with AI agents, enabling seamless orchestrated trips and improved venue discovery based on traveller AI Profiles and Character settings. Taash's Context-Aware Discovery and Social Matching Engine can address these friction points, facilitating coordinated booking and matching travellers with the right venues.