Many organizations start with internal tooling for cost reporting and chargeback. Over time, requests expand: deeper allocation, more dimensions, faster accountability loops, policy-based governance, and extensibility across platforms. This session uses Lyft’s experience as a reference point and guides participants through a structured decision framework: what signals indicate the internal tool is becoming a drag, how to quantify engineering and operational burden, how to gather requirements from stakeholders, and how to run a vendor evaluation without stalling progress. The deliverable is a set of decision criteria and an evaluation worksheet attendees can take back to their org.