# Director, Chief of Staff

**Company**: PayPal
**Location**: San Jose, California
**Work arrangement**: hybrid
**Experience**: executive
**Job type**: full-time
**Salary**: $159,500.00 - $236,500.00 Annually
**Category**: Finance
**Industry**: Finance

**Apply**: https://paypal.wd1.myworkdayjobs.com/en-US/jobs/job/San-Jose-California-United-States-of-America/Chief-of-Staff_R0138332-1?utm_source=yubhub.co&utm_medium=jobs_feed&utm_campaign=apply
**Canonical**: https://yubhub.co/jobs/job_d064619e-0ad

## 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

## Skills

### Required
- strategy
- strategic planning
- investment analysis
- finance
- consulting
- business operations
- analytical discipline

### Nice to have
- AI
- emerging technology

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