Chief of Staff

The Company PayPal has been revolutionizing commerce globally for more than 25 years. Creating innovative experiences that make moving money, selling, and shopping simple, personalized, and secure, PayPal empowers consumers and businesses in approximately 200 markets to join and thrive in the global economy. We operate a global, two-sided network at scale that connects hundreds of millions of merchants and consumers. We help merchants and consumers connect, transact, and complete payments, whether they are online or in person. PayPal is more than a connection to third-party payment networks. We provide proprietary payment solutions accepted by merchants that enable the completion of payments on our platform on behalf of our customers. We offer our customers the flexibility to use their accounts to purchase and receive payments for goods and services, as well as the ability to transfer and withdraw funds. We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account balance, PayPal and Venmo branded credit products, a credit card, a debit card, certain cryptocurrencies, or other stored value products such as gift cards, and eligible credit card rewards. Our PayPal, Venmo, and Xoom products also make it safer and simpler for friends and family to transfer funds to each other. We offer merchants an end-to-end payments solution that provides authorization and settlement capabilities, as well as instant access to funds and payouts. We also help merchants connect with their customers, process exchanges and returns, and manage risk. We enable consumers to engage in cross-border shopping and merchants to extend their global reach while reducing the complexity and friction involved in enabling cross-border trade. Our beliefs are the foundation for how we conduct business every day. We live each day guided by our core values of Inclusion, Innovation, Collaboration, and Wellness. Together, our values ensure that we work together as one global team with our customers at the center of everything we do – and they push us to ensure we take care of ourselves, each other, and our communities. Job Summary: The Director, Chief of Staff is a strategic partner to the Chief AI Transformation & Simplification Officer, owning the analysis, models, investment cases, and executive communications that guide AI investment decisions. The role blends classic Chief of Staff duties with AI strategy, opportunity sizing, business-case development, financial modeling, and executive decision support. Key duties: manage the executive operating rhythm (staff meetings, business reviews, offsites) and prepare briefings and decision materials; lead AI investment cases, including sizing, cost/benefit assumptions, and sensitivity analysis; build models comparing initiatives, investment levels, and resources; craft executive narratives for the CEO, ELT, and Board; coordinate with business, tech, finance, and corporate functions to track decisions and risks. High-visibility, enterprise-facing role requiring financial acumen, structured analysis, and influence-based leadership without direct-line authority. Job Description: Essential Responsibilities: • Establish overall business or technical strategy for the business operations of aligned organization. • Influence decisions as an advisor or counsel to business leadership. • Drive strategic objectives and ensure resources are effectively allocated. • Provide oversight and support for planning and management of financial, budget, and headcount targets. • Act as a liaison between business leadership, staff, and other key partners. • Optimize workflows and drive process improvements to enhance organizational performance. • Drive and monitor Objectives and Key Results (OKRs) to address gaps in business and operations. Minimum Qualifications: • 10+ years relevant experience and a Bachelor’s degree OR Any equivalent combination of education and experience. Additional Responsibilities & Preferred Qualifications : Significant experience in strategy, strategic planning, investment analysis, finance, consulting, business operations, or a related analytical discipline. Demonstrated ability to build, interpret, and explain financial, business, and strategic models used to support investment and executive decisions. Experience developing business cases, sizing opportunities, testing assumptions, and evaluating scenarios or investment tradeoffs. Strong executive communication skills, including experience developing presentations, narratives, and decision materials for senior audiences. Ability to synthesize ambiguous and complex information into practical recommendations and clear next steps. Strong organizational, relationship-building, and project leadership skills in a matrixed environment. Experience working across business and technology teams; knowledge of AI and emerging technology is preferred. Subsidiary: PayPal Travel Percent: 0 - The base pay for this role will depend on where you work and the relevant experience and expertise you bring. The expected range of pay for this role by location is: Primary Location | Pay Range: San Jose, California: ($159,500.00 - $236,500.00 Annually) Additional Location(s) | Pay Range: No other locations are assigned to this requisition currently. Additional compensation for this role may include an annual performance bonus, equity, or other incentive compensation, as applicable. PayPal does not charge candidates any fees for courses, applications, resume reviews, interviews, background checks, or onboarding. When making an application directly, we will never ask you to share passwords, one-time passcodes (OTP), or verification codes. Any such request is a red flag and likely part of a scam. All communication regarding your application will come from official PayPal email domains. If you suspect fraudulent activity, please report it imme