Shopmonkey, a rapidly growing company in the retail automotive repair industry, faced challenges with data consistency and scaling due to their monolithic application's technical debt. To address this, they re-architected their system using CockroachDB as a managed Database as a Service (DBaaS), enabling highly available and geo-aware database solutions for their widespread user base across North America. This transition required a shift in database design thinking and involved retraining developers to adapt to a distributed mindset. The new architecture includes a setup with three super regions, nine nodes, and custom tools like a connection pooler and a schema change tool named Wrench, ensuring regional consistency and load distribution. CockroachDB's managed service alleviates database operations, allowing Shopmonkey to focus on business-differentiating features, with support available for troubleshooting and optimization.