Small and Medium-sized Businesses (SMBs) in Southeast Asia prioritise cashflow management, expense control, and budgeting to maintain financial health despite limited resources and a dispersed workforce. CFOs and finance teams play a strategic role in driving operational excellence, yet challenges arise from inadequate oversight of employee spending, leading to inefficiencies. Aspire’s financial data remains underutilised as finance teams manually extract insights through repetitive tasks like data collection, cleaning, and reconciliation—hindering strategic decision-making. The overwhelming volume of transactional data and alerts often results in missed anomalies and updates. This project adopts a human-centric, data-driven approach to: 1) Enhance decision-making to reduce costs, 2) Automate workflows for efficiency, and 3) Enable collaboration for distributed teams. Leveraging AI-driven analytics, the solution provides clear visibility into financial operations while ensuring security through access control. User validation confirmed the benefits of in-context intelligence over generic AI chatbots for workflow optimisation.