PayPal Insider Sales What PYPL Bears See Coming

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•  16 Nov 2025
 

•   PYPL  
   
  -9.84%

When three senior executives at a company sell over $1.5 million in shares within two weeks, markets notice. When one of them dumps his entire position, markets worry. That's exactly what happened at PayPal Holdings in late October and early November, and the timing tells a story that quarterly earnings couldn't hide.

Chris Natali, the CFO responsible for accounting oversight, sold all 1,374 shares on October 30th at $69.13 each. Not most of his holdings. All of them. He walked away with roughly $95,000 and left himself with zero skin in the game. Three days later, Susan Kearier, president of global markets, unloaded 12,500 shares across two transactions at an average price around $68.90, pocketing $860,000. She kept 31,000 shares worth nearly $2 million, so she's not abandoning ship entirely, but she's clearly lightening the load. Then Aaron Webster, the global head of risk, closed out the wave on November 10th with three separate sales totaling 9,282 shares for about $615,000. The man paid to manage risk decided to reduce his own.

These sales came right after $PYPL reported third quarter results on October 28th. The numbers looked solid on paper. The company beat Wall Street's expectations with adjusted earnings of $1.34 per share versus the $1.20 consensus, and revenue climbed to $8.4 billion against forecasts of $8.2 billion. Total payment volume grew seven percent to $458.1 billion. Management even announced the company's first dividend of $0.14 per share and unveiled a partnership with OpenAI to integrate PayPal payments into ChatGPT. By any traditional measure, this was a strong quarter.

The market disagreed. PYPL shares dropped 14% in the days following the report. Since then, the stock has continued bleeding, down 26% year to date while the S&P 500 climbed 14%. That divergence matters. PayPal traded above $300 during its 2021 peak. Today it hovers around $62. The gap between then and now represents more than just a valuation reset. It reflects a fundamental shift in how investors view the company's competitive position.

CEO Alex Chriss, who took over in 2023, has been methodically refocusing the business on profitable core operations and away from low-margin volume chasing. The strategy makes sense in theory. Branded checkout activity, which generates higher margins, represented 31% of total payment volume in Q3. The problem is that online purchases through branded channels only grew five percent. Transaction counts fell five percent overall to 6.3 billion, though they showed seven percent growth when stripping out unbranded activity. Transactions per active user dropped six percent to 57.6 annually, reversing to five percent growth when adjusted for strategic exits from unprofitable segments.

These aren't bad numbers. They're the numbers of a company executing a deliberate pivot. But investors in payments and fintech want growth, not optimization. They want proof that PayPal can compete against Stripe, Block, and the dozens of embedded finance providers that didn't exist five years ago. Regional headwinds don't help. Europe, particularly Germany, remains sluggish. Cross-border payment flows between the US and China are still recovering from disruptions earlier this year.

Citi initiated coverage with a neutral rating, acknowledging PayPal's two-sided marketplace and brand strength while noting that branded checkout growth remains the critical metric to watch. The firm's caution reflects a broader uncertainty. Fintech performance this year has been wildly inconsistent. Affirm is up 16% while Block has fallen 29%. PayPal sits firmly in the middle, trapped between value investors who see a turnaround story and growth investors who see a mature platform losing share.

The insider sales don't automatically signal disaster. Executives sell shares for personal reasons all the time, and some of these transactions may have been scheduled months in advance. But when the CFO exits his entire position days after an earnings report that sent shares tumbling, and when the head of risk reduces exposure during a period of obvious strategic uncertainty, the optics are brutal. These are the people with the clearest view into what's actually happening inside the company. Their actions suggest they're not confident enough in the near-term trajectory to hold through volatility.

PayPal's challenge isn't existential. The company still processes nearly half a trillion dollars in payment volume annually and generates billions in free cash flow. The dividend initiation signals management's confidence in that cash generation. The OpenAI partnership could open meaningful distribution channels as AI tools become more integrated into commerce. But confidence in financial stability isn't the same as confidence in competitive positioning. The payments landscape has evolved faster than PayPal has adapted, and competitors aren't waiting around.

PYPL at current levels represents a bet on operational execution and multiple expansion in an environment where neither is guaranteed. The valuation has compressed significantly from pandemic highs, which creates theoretical upside if management delivers on the turnaround narrative. But the insider selling, combined with persistent concerns about branded checkout growth and regional weakness, suggests the path to that upside is longer and less certain than bulls hoped after the Q3 report. When the people running the business are reducing their own exposure, it's worth asking what they see that the earnings presentation didn't show.

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