When faced with the challenge of converting 8 highly technical journals spanning 95 years, how do you divide responsibility between the content owner and the conversion vendor? Do you spend a year on document analysis and developing conversion specifications, or do you hand the project over to a well-regarded service provider and rely on their expertise entirely? This paper demonstrates how an agile approach to content conversion with close collaboration between the publisher and the conversion vendor has allowed The Optical Society (OSA) and Data Conversion Laboratory, Inc. (DCL) to navigate between the two extremes and create a high-quality digital archive that will serve OSA's strategic aims for developing innovative products and services.