This session outlines data-driven best practices and templates from speaker's engineering leadership experience in Amazon, Microsoft, EA, and Visa in leading large scale product development. We will cover various mechanisms for measuring, executing, and auditing software engineering projects. We will use practical examples and templates to outline proven techniques for 1) estimation, planning (roadmapping), and execution (weekly, monthly, quarterly mechanisms), 2) measuring and auditing developer metrics to increase individual and team productivity, and 3) implementing observability for system metrics for capturing availability, performance/latency, and error reporting, and implementing self-healing capabilities.