Uganda's informal service sector—employing 70% of working Ugandans—suffers from severe marketfragmentation characterized by trust deficits and information asymmetry. We developed ClickToAssist,an AI-powered platform engineered specifically for Uganda's context. Through field testing acrossKampala with 250 verified service providers and 1,200 customers, we implemented community-basedverification and culturally intelligent matching algorithms incorporating neighborhood reputationnetworks, language compatibility, and local context. Results demonstrated an 87% reduction in servicesearch time (from 3.2 days to 4.7 hours), 76% higher customer satisfaction, and a 63% decrease inincome variance for service providers. Our AI matching achieved 92% accuracy by addressingcontextual factors global platforms overlook. This research demonstrates that contextually intelligenttechnology can effectively transform fragmented service markets in the Global South