The shift to remote work due to COVID-19 has posed significant challenges for IT and security teams, as seen at PagerDuty, where a large portion of employees transitioned to remote work almost overnight. Key lessons learned in managing this transition include securing hardware, balancing privacy with necessary oversight, simplifying user experiences, and maintaining open communication. Hardware security is crucial, especially given the increase in equipment use on potentially unsecured networks, and requires encryption and remote management tools. Privacy concerns necessitate a balanced approach to monitoring, avoiding invasive tactics like keylogging. Enhancing user experience by providing secure and user-friendly applications can prevent employees from seeking risky alternatives. Regular communication about potential risks and updates is essential to keep staff informed and secure, particularly as public WiFi usage becomes more prevalent. To assist other organizations, PagerDuty has made its internal security training materials publicly available, allowing businesses to adapt these resources to maintain security in an evolving work environment.