Checkly enables engineers to automate the monitoring of their production services using Playwright, an automation framework. The goal is to find the right cadence for site checks, balancing frequency with minimizing unnecessary noise and ensuring timely alerts. This involves understanding service level agreements (SLAs), defining a mean time to detect (MTTD) failure, setting retry logic, scheduling dynamically based on region, and balancing with comprehensive monitoring. By refining the approach through feedback loops, engineers can continuously improve their monitoring strategy, ultimately setting themselves up for success in maintaining uptime, meeting SLAs, and delivering a seamless experience for users.