Many insurers are struggling to keep up with changing customer dynamics and expectations, especially in the new COVID world. Organizations understand the gains to be made if they digitize their legacy systems, but the days when project teams could take months, or multi-month cycles to deploy a new product or feature are over. The need for change is clear, yet insurers are challenged by the prospect of a long and expensive core system upgrade. However, by not properly investing in technology platforms and systems, insurers accrue another type of cost: technical debt. How can they find the right path to move forward?