With the vast majority of its sales taking place via third-party vendors like Best Buy, Microsoft must incentivize active selling by wage-labor retail sales professionals (RSPs) despite the lack of any additional material reward. Anemic performance in this enormous space spurred key Microsoft business groups to seek powerful design solutions to reverse this trend. Parliament was approached to completely rethink, redesign, and strategize a comprehen- sive coursework system that would compel RSPs to learn deeply, engage consumers, and pursue high sales at all interaction points. Our initial work with Windows 7—which entailed a complete training reboot and the creation of dozens of courses—led to further, and similarly intensive, work with the Office for Mac and Point of Sale Activation groups. Our training-coursework design and information architecture has since been disseminated and adopted as the global standard among all Microsoft business groups.