Rumors are that a substantial organizational change at PayPal is in progress. Frankly, it’s overdue. For any global payments company to succeed, its leaders must possess a deep, almost intuitive, understanding of the global payments ecosystem. This is where PayPal is currently failing.

We have a CEO, Alex Chriss, known as a product specialist. While he may be excellent at getting products out the door, this is not the problem PayPal faces. Unfortunately, the team can’t see the forest fire given their conspicuously poor payment background. For example, look at Diego Scotti as EVP and GM of the consumer group. His experience comes from Verizon, and his chief credential is that he is the husband of Janey Whiteside, one of Alex’s closest payment advisors. When growth doesn’t happen and targets get missed, investors begin to look for the reasons and the resumes of those running the ship.

In payments, merchants “pay for everything”. Understanding their needs is not just important; it is paramount. This is precisely why Bill Ready was the best COO PayPal ever had. Coming in as the CEO of Braintree (which PayPal acquired), Bill knew merchants inside and out. His departure left a void in merchant understanding that has yet to be filled. The other exec who knew retailers was John Rainey (now CFO of Walmart). While replacing this talent is nearly impossible, the template was there. Here, I would point to a BOD failure. 

Today, PayPal pushes out products that are disconnected from a coherent strategy and GTM plan. The PYUSD stablecoin, the revamped PayPal Rewards program, and a new “data business” all operate in silos. They are features in search of a strategy, not components of a unified value proposition. 

Don’t just take my word for it. In a recent merchant survey I conducted, the feedback was consistent and damning. A CMO at a top 50 online retailer told me, “PayPal is no longer best in class in conversion or auth rates (ShopPay and ApplePay lead here), branded also operates at a substantial premium. While 10% of my customer base uses them, PYPL is not growing. I won’t be doing anything new with PayPal as they are no longer strategic, and they need to fix the pricing before I even consider partnering with them.”

This brings us to PayPal’s valuation. The company is trading at a ~17x multiple not because it’s a bad company, but because its growth has evaporated (Seeking Alpha). Investors look at the competitive landscape and see checkout buttons like Stripe Link, Shop Pay, and Apple Pay rapidly gaining transaction share at PayPal’s expense. These services are integrated, simple, and operate at NO PREMIUM for merchants. They are winning the future of online checkout while PayPal defends the past.

Perhaps PayPal’s biggest failure of the last five years is its inability to gain meaningful traction at the physical point of sale (POS) with Venmo. A new generation of consumers doesn’t think in terms of plastic cards; they think of paying with their phone, and they want to pay with Venmo. This massive opportunity was missed not because of a product failure, but because of a catastrophic sales, partnership, and pricing failure. The company simply did not know how to sell it to merchants.

PayPal has all the pieces to be a great company. It has a globally recognized brand and a massive user base. But it requires an experienced leader to unite the business with a clear strategy, not a product manager to just push out more features. Dan’s previous “super app” strategy was a flawed attempt to create a common UI to mask the lack of a unified business strategy (see 2021 Super App Blog). 

To grow again, PayPal must take decisive action:

1. Install a leadership team that knows global payments. This is non negotiable. The executive team must have deep expertise in partnerships, merchant acquiring, and the complexities of retail.
2. Fix the merchant value proposition. This means competitive pricing, superior authorization rates, and a clear, strategic partnership model. Stop treating merchants like a utility.
3. Integrate the assets. Create a seamless experience that connects PayPal checkout, Venmo, Braintree, and rewards into a flywheel that benefits both consumers and merchants.

An organizational change is the necessary first step. But without the right people leading that change, it will just be rearranging deck chairs on a ship that has lost its course.