Description
The Director, Chief of Staff is a strategic partner to the Chief AI Transformation & Simplification Officer, owning analysis, models, investment cases, and executive communications that guide AI investment decisions.
Key duties:
- Manage the executive operating rhythm 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
The role requires financial acumen, structured analysis, and influence-based leadership without direct-line authority.
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
Benefits:
- Comprehensive, choice-based programs to support all aspects of personal wellbeing
- Generous paid time off
- Healthcare coverage for you and your family
- Resources to create financial security and support your mental health
Work Environment:
- 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