Monitoring deployment frequency is crucial for achieving and surpassing goals in a DevOps strategy, as it measures how often code is deployed to production or an app store. Top-performing companies identify frequent deployment as a measure of success, with elite teams deploying multiple times per day and low performers deploying only once every six months. Measuring deployment frequency offers insights into the efficacy of DevOps practices within a company, helping organizations understand their workflow, identify broader issues, and make data-driven goals to improve upon it. By regularly assessing deployment frequency, companies can differentiate between high and low performing teams, and use this metric as a barometer for success in achieving continuous delivery and shipping code quickly and frequently.