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 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.
