To effectively monitor software at scale, organizations need to adopt automation best practices. At New Relic, they use four key strategies: automating monitoring agent installation in application builds, adding markers and tags to deploy systems, bootstrapping applications with monitoring, and using APIs and Domain Specific Languages (DSLs) for dashboards and alerting. By automating these tasks, organizations can reduce boilerplate code, eliminate manual configuration errors, and make it easier to manage complex microservices architectures. This approach not only improves monitoring efficiency but also reduces toil and uncertainty in operations, allowing teams to focus on innovation rather than manual monitoring tasks.