The accumulation of technical debt is a well-documented problem, stemming from issues including security vulnerabilities, lack of agility, errors, instability, and high system costs. This case study examines how Nationwide Insurance and other enterprises use realistic expectations, capability mapping, process automation tools, technology reclassification, and collaboration to drive success. This approach can reduce the number of systems in use by 40%, improving agility, talent retention, and the firm’s innovation roadmap.