In late 2019 and early 2020, Illinois’ Central Management Services (CMS) launched two innovative initiatives to foster employees’ resilience and agility. Be Well Illinois is a wellness program designed to address the physical, mental, and financial health needs of more than 440,000 State employees, retirees, and their dependents. CMS University is a web portal that provides continuing education and resources that are specifically curated for CMS staff. This state spotlight examines the creation of these initiatives and the leadership challenges and opportunities that emerged as they developed. It explores strategies to support employees’ mental health and wellness, the role of leaders in advancing diversity, equity, and inclusion, and building resilient and agile organizations.