Insurance modernization efforts have been a focus for decades now. Still, the process is lengthy and many organizations are still considering the right approach for their policyholders, employees, and stakeholders. While a cursory treatment of the subject can’t possibly provide the level of in-depth bespoke analysis that partnering with a systems integrator will ultimately yield, this paper is meant to provide some of the most common considerations for organizations looking for guidance as they evaluate where to start their digitalization journey. This can often be a challenge, especially with vendors eager to paint a rose-colored future primarily based on their particular offering–perhaps with feature sets that only muddy the waters.