PayPal Holdings Inc. faces mounting pressure to break apart its portfolio. Dan Schulman, the company’s CEO at the time, pushed back hard against rumors of selling off Venmo and Braintree. He argued those units formed the core of PayPal’s strength, according to a briefing from The Information. Investors weren’t convinced. Fast forward to 2026. The board has cycled through leaders. Now, fresh CEO Enrique Lores is carving up the business anyway.
Venmo. Nearly 100 million users strong. It’s PayPal’s bridge to younger crowds. Braintree handles big enterprise clients, processing unbranded payments for giants like Uber. Together, they promised synergies. Schulman saw them as indispensable. But growth stalled. Checkout volumes lagged competitors. Venmo’s monetization dragged.
And then the shakeup hit. In late April, PayPal announced three standalone units: Checkout Solutions & PayPal, Consumer Financial Services & Venmo, and Payment Services & Crypto. Braintree slots into that last one, alongside digital asset operations. Lores, fresh from HP, declared, “To accelerate growth and unlock our full potential, we need to recommit to our fundamentals—getting much closer to the consumer, aligning the company around three strong businesses, simplifying how we work, sharpening accountability, and prioritizing operational excellence,” as reported by The Wall Street Journal.
CNBC broke the news first. Sources said the Venmo split makes tracking easier. Or selling. Shares jumped 3% that day, per CNBC. Two executives departed amid the changes. PayPal hunts a digital banking leader for Venmo. An AI transformation group launches too, headed by ex-Walmart tech exec Anshu Bhardwaj.
Why now? PayPal’s stock shed 80% from pandemic highs. Branded checkout grew just 1% last quarter. Venmo revenue hit $1.7 billion in fiscal 2025, up 20%. Yet overall, the company sputters. Competitors like Stripe, Apple Pay, and Google gobble share. Braintree fights pricing wars. Venmo chases profitability.
Analysts eye buyers. Stripe tops lists. PayPal’s $40 billion market cap looks cheap against Stripe’s $159 billion valuation. Braintree adds $700 billion in payment volume. Venmo fills consumer gaps. “Selling off Venmo might make sense, but Kupferberg expects investors will push PayPal to make ‘bolder’ moves now to ‘maximize’ the value of the company,” notes Payments Dive. Apple? Possible fit for e-commerce push. Banks like JPMorgan dream of super apps. Private equity lurks, eyeing carve-outs.
But synergies? PayPal insists they exist. Lores’ structure tests that claim. Consumer Financial Services builds Venmo into a full platform. Payment Services bundles Braintree with crypto. Checkout stands alone. Frank Keller leads checkout. Interim heads fill other spots. Scott Young runs supporting financial services.
History repeats. Schulman retired end-2023 after growth faltered post-COVID. Alex Chriss took over, promised revival. Fixed Braintree go-to-market. Venmo monetized slowly. Still, Q4 misses led to his exit. Lores, board chair, steps in March 2026. Now cuts loom—20% staff reduction announced this week, per WSJ. First-quarter profit dipped to $1.11 billion.
Critics pile on. Former execs lament lost edge. David Marcus, early PayPal leader, blasted the drift in a viral post. Product gave way to finance. Volume chased over margins. BNPL became a feature, not a weapon. Acquisitions like Honey distracted. PayPal optimized short-term. Long-term vision faded.
Markets shrug at full buyouts. Cultural clashes. Tech debt. 25,000 employees. Regulators loom for Visa, Mastercard, Big Tech. X chatter echoes frustration. Investors want transformation or divestitures. Venmo as Gen-Z lifeline. Braintree for enterprise scale. Sell high-value pieces. Return cash.
Lores bets on focus. Three units sharpen accountability. AI group attacks complexity. But questions linger. Will Venmo fetch $5 billion spun off? Braintree draw Stripe? Or does integration win? PayPal processed billions in volume last year. Free cash flow tops $5 billion. Assets gleam. Execution decides.
Schulman’s defense feels distant. Units separate. Speculation boils. PayPal’s next chapter hinges on sales—or bold revival.
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