10-Q, Member Exclusive

Inside Alex Chriss’s first year leading PayPal

  • On September 27, 2023, PayPal began a new chapter with Alex Chriss stepping into the CEO role.
  • A year into his tenure, we take a look at Chriss's journey at PayPal through key events and if he is winning approval.
close

Email a Friend

    It’s nearly been a year already — How is Chriss’s journey progressing?

     

    As fall approached last year, PayPal began a major transformation: a change in leadership. While CEO transitions are not uncommon, this one stood out for PayPal. Daniel Schulman, who had been steering the ship since 2014, was departing. Schulman’s tenure was marked by pivotal moments, including the company’s spin-off from eBay and its evolution into an independent, publicly traded entity. Under his leadership, PayPal redefined itself and expanded its global reach. His departure left considerable expectations for his successor, who would need to navigate not only the legacy of Schulman’s transformative years but also address the company’s challenges at the time, including its underperforming stock that had lost nearly 20% value year-to-date and dwindling active user numbers.

    On September 27, 2023, PayPal began a new chapter with Alex Chriss stepping into the CEO role.

    As the industry digitizes, PayPal’s board sought a leader with a blend of expertise in global payments and technology to drive the company’s growth. When Chriss, who was employed at Intuit, was appointed from a pool of nine candidates, the board expressed strong confidence in their choice. However, the broader industry and analysts had a relatively tepid response, reflecting a cautious curiosity about how Chriss would steer PayPal into its next phase

    A year into his tenure, we take a look at Chriss’s journey at PayPal through key events.


    subscription wall for TS Pro

    0 comments on “Inside Alex Chriss’s first year leading PayPal”

    Member Exclusive, Opinion

    The infrastructure paradox: The better you become, the harder customers are to keep

    • Financial infrastructure is becoming part of the business itself, changing what customers are willing to outsource.
    • Providers now have to grow with their customers and keep expanding their value as those customers begin to question how much of the stack they should continue to outsource.
    Sara Khairi | September 04, 2026
    Business of Fintech, Member Exclusive

    Financial firms are building new businesses from the layers beneath their products

    • Intuit is opening up its financial intelligence to AI agents, while SoFi is making its infrastructure programmable.
    • Both firms are betting that the layers beneath their products can become businesses in their own right, creating value across new interfaces, businesses, and customer relationships.
    Sara Khairi | September 03, 2026
    Business of Fintech, Member Exclusive, Policies & Playbooks

    The antitrust question is moving up the stack: What California’s new push and NVIDIA’s retreat mean for finance

    • California lawmakers are weighing whether antitrust law needs to draw a clearer line between growing an ecosystem and using market power to shape it.
    • Antitrust is now becoming a front-end strategy issue for financial services, not a back-end legal concern.
    Sara Khairi | September 02, 2026
    10-Q, Member Exclusive

    Goldman Sachs built its talent pipeline around apprenticeship. AI is now testing what that means

    • How does the apprenticeship model evolve when AI takes over the work that once taught the trade?
    • AI can accelerate junior employees’ output while slowing the learning curve that once came from doing the work themselves.
    Sara Khairi | August 31, 2026
    5 questions, Banking, Member Exclusive, SMB Finance

    ‘Traditional banks have equated advising with cross-selling’: Grasshopper’s Danielle Kane on why just 7% of SMBs see banks as trusted advisors

    • Only 7% of SMB owners see their banks as trusted advisors, exposing a gap between transactional services and the strategic support they need.
    • Grasshopper’s Danielle Kane says the SMB-bank relationship needs to shift from more tools to proactive guidance that helps businesses navigate complexity and scale.
    Javarya Kamran | August 27, 2026
    More Articles