Code is the easy part, or how we refactored half the business to fix a janky script
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A startup engineering war story about refactoring a broken billing system at Plasmidsaurus as the company scaled from $20M to near $100M ARR. The core insight: the real problem wasn't the janky Python invoicing script but a misaligned data model. The fix required introducing 'billing entities' as a new abstraction, migrating from QuickBooks to Rillet, building self-service tools for users and finance, and rewriting the invoicing script with proper tests. The process took 6 months, involved 6+ people, required extensive user interviews and watching people work, and was shipped incrementally to avoid breaking a live system processing thousands of orders daily. Result: month-end invoicing dropped from a week-long ordeal to 2 days.
