Director of AI Strategy & Investment Execution

BAM Ventures; San Jose (CA); Hybrid; USD 160,000 - 237,000; Full time

Benefits offered by this job

Hybrid work model

Health benefits

Equity/bonus

Job summary

PayPal is seeking a Director, Chief of Staff to partner with the Chief AI Transformation & Simplification Officer. You will own analyses, models, investment cases, and executive communications to guide AI investments.

Responsibilities include managing the executive operating rhythm, leading investment cases, building financial models, and crafting narratives for the CEO and Board. Strong leadership without direct authority is required.

Qualifications

• Significant experience in strategy, strategic planning, investment analysis, finance, or related analytical discipline.
• Demonstrated ability to build, interpret, and explain financial, business, and strategic models.
• Experience developing business cases, sizing opportunities, testing assumptions, and evaluating scenarios.

Responsibilities

• Establish overall business or technical strategy for the operations of the aligned organization.
• Influence decisions as an advisor to business leadership.
• Drive strategic objectives and ensure resources are allocated effectively.
• Oversee planning and management of financial, budget, and headcount targets.
• Act as a liaison between leadership, staff, and partners.
• Optimize workflows and drive process improvements to boost performance.
• Lead and monitor OKRs to address gaps in business.

Skills

Strategic planning

Investment analysis

Financial modeling

Executive communication

OKRs

Cross-functional collaboration

Education

Bachelor’s degree

Job description

PayPal is seeking a Director, Chief of Staff to partner with the Chief AI Transformation & Simplification Officer. You will own analyses, models, investment cases, and executive communications to guide AI investments.

Responsibilities include managing the executive operating rhythm, leading investment cases, building financial models, and crafting narratives for the CEO and Board. Strong leadership without direct authority is required.