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This case places students in the position of Alex Chriss, the newly appointed Chief Executive Officer of PayPal, as he prepares for a critical board strategy review in October 2024. Despite leading one of the world’s largest digital payments platforms, processing over $1.5tn in total payment volume annually and serving more than 430 million active accounts globally, Chriss inherited a company under significant strategic pressure. Revenue growth had slowed, share price performance was deteriorating and analysts were increasingly describing PayPal as a mature incumbent rather than a platform innovator.

The organizational inflection point is a dilemma with no comfortable resolution....

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