PayPal
Chief of Staff
$160K–$236K
San Jose, California, United States of America · Staff · Full-time · Posted Oct 1, 2026
- Experience
- 10+ years relevant experience; alternatively, an equivalent combination of education and experience.
- Education
- Bachelor’s degree or equivalent combination of education and experience.
About the job
Partners with PayPal’s Chief AI Transformation & Simplification Officer to shape AI investment decisions through analysis, financial modeling, executive communications, and operational leadership.
What you'll do
- Manage executive meetings, reviews, offsites, briefings, and decision materials.
- Develop AI investment cases and models, including opportunity sizing, cost-benefit assumptions, sensitivity analysis, and investment tradeoffs.
- Coordinate across business, technology, finance, and corporate teams; track decisions and risks, and communicate recommendations to senior leaders.
What they ask for
- 10+ years of relevant experience and a Bachelor’s degree, or an equivalent combination of education and experience.
- Experience in strategy, strategic planning, investment analysis, finance, consulting, business operations, or a related analytical discipline.
- Ability to build, interpret, and explain financial, business, and strategic models and develop business cases.
- Strong executive communication and ability to synthesize complex information into practical recommendations.
Nice to have
- Experience working across business and technology teams.
- Knowledge of AI and emerging technology.
Pay
USD 159,500.00 - USD 236,500.00 annually (base salary)
AI focus
Leads AI investment analysis, opportunity sizing, business-case development, and financial modeling to support executive investment decisions.
Model-written summary · the original posting is authoritative