The case follows PayPal, a digital payments platform that found early success processing online payments for purchases on eBay, which acquired the company in 2002. The case begins by describing the decision by eBay in 2014 to spin off PayPal and the strategic challenges facing its new CEO, Dan Schulman, who encountered significant strategic issues leading PayPal as an independent company. When the separation from eBay finalized in July 2015, PayPal was in the midst of a multi-year technology reconstruction. Additionally, the digital payments landscape had changed dramatically, extending beyond eCommerce into mobile payments, global remittances, peer-to-peer transfers, and offline transactions. The case presents several trials facing Schulman, including how to innovate quickly in a large organization, whether and how to recreate PayPal's vision, and how to both partner and compete successfully with new entrants in the market.