This conference talk explores Octopus Deploy's multi-year journey to improve reliability across their 18,000+ CI tests for a monolithic product. Follow along as Cail Young shares how Service Level Objectives (SLOs) function as organizational warning systems, indicating both when intervention is necessary and when allowing failures is appropriate. Discover practical insights about managing goal conflicts, prioritization strategies, safety models, and professional development within a rapidly growing company. Learn how SLOs can be implemented as effective monitoring tools that guide engineering decisions and organizational responses to system reliability challenges.