Chief of Staff

PayPal•San Jose, CA
•$159,500 - $236,500•Hybrid

About The Position

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.

Requirements

  • 10+ years relevant experience and a Bachelor’s degree OR Any equivalent combination of education and experience.

Nice To Haves

  • 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.

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.

Benefits

  • Generous paid time off
  • Healthcare coverage for you and your family
  • Resources to create financial security
  • Support your mental health
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