Chief of Staff

PayPal; San Jose (CA); Hybrid; USD 160,000 - 237,000; Full time

Benefits offered by this job

Hybrid work model

Healthcare coverage

Generous paid time off

Job summary

PayPal is seeking a Director, Chief of Staff to partner with the Chief AI Transformation & Simplification Officer. You will own analysis, financial models, investment cases, and executive communications guiding AI investments.

The role blends Chief of Staff duties with AI strategy, sizing opportunities, and business-case development across our enterprise. The position requires strong financial acumen, cross-functional collaboration, and the ability to influence decision makers without direct

Qualifications

• 10+ years relevant experience and a Bachelor's degree.
• Experience in strategy, strategic planning, investment analysis, finance, consulting, business operations, or a related analytical discipline.
• Strong executive communication skills for senior audiences.

Responsibilities

• Establish overall business or technical strategy for the operations of the aligned organization.
• Influence decisions as an advisor to business leadership.
• Drive strategic objectives and ensure resources are allocated effectively.
• Provide oversight for planning and management of financial, budget, and headcount targets.
• Act as a liaison between leadership, staff, and key partners.
• Optimize workflows and drive process improvements for better performance.
• Drive and monitor OKRs to address gaps in business and operations.

Skills

Strategic planning

Investment analysis

Financial modeling

Executive communication

Education

Bachelor's degree

Job description

The CompanyPayPal 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:PayPalTravel 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 immediately. To learn more about how to identify and avoid recruitment fraud please visit https://careers.pypl.com/contact-us.For the majority of employees, PayPal's balanced hybrid work model offers 3 days in the office for effective in-person collaboration and 2 days at your choice of either the PayPal office or your home workspace, ensuring that you equally have the benefits and conveniences of both locations.Our Benefits:At PayPal, we’re committed to building an equitable and inclusive global economy. And we can’t do this without our most important asset-you. That’s why we offer comprehensive, choice-based programs, to support all aspects of personal wellbeing—physical, emotional, and financial—delivering meaningful value where it matters most. We strive to create a flexible, balanced work culture with a holistic approach to benefits, including generous paid time off, healthcare coverage for you and your family, and resources to create financial security and support your mental health.Who We Are:Commitment to Diversity and InclusionPayPal provides equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, pregnancy, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state, or local law. In addition, PayPal will provide reasonable accommodations for qualified individuals with disabilities. If you are unable to submit an application because of incompatible assistive technology or a disability, please contact us at [e-mail] at PayPal:Our employees are central to advancing our mission, and we strive to create an environment where everyone can do their best work with a sense of purpose and belonging. Belonging at PayPal means creating a workplace with a sense of acceptance and security where all employees feel included and valued. We are proud to have a diverse workforce reflective of the merchants, consumers, and communities that we serve, and we continue to take tangible actions to cultivate inclusivity and belonging at PayPal.Any general requests for consideration of your skills, please Join our Talent Community.We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates. Please don’t hesitate to apply.