No insurance company is immune from the impact of digital transformation. Established insurers are dealing with an onslaught of forces that range from escalating customer expectations to the hundreds of monoline disruptors and big tech firms like Amazon and Google exerting growing influence as platforms. These forces spurred the Colorado workers' compensation insurer Pinnacol Assurance to launch a new digital subsidiary, Cake. This case study examines how the century-old insurer beat expectations and deadlines in its quest to outrun these emerging threats.