Director, Chief of Staff

PayPal; Chicago (IL); Hybrid; USD 145,000 - 215,000; Full time

Benefits offered by this job

Hybrid work model

Healthcare coverage

Generous paid time off

Job summary

PayPal in Chicago seeks an senior strategic advisor to shape business and technical direction for the organization. You will devote substantial effort to strategy and executive-level decision-making to guide the company's operations and growth.

The role demands 10+ years of relevant experience and a Bachelor’s degree, with a hybrid work model offering in-office and remote days. Compensation aligns with location and expertise, with potential additional incentives.

Qualifications

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

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.

Education

Bachelor’s degree or equivalent

Job description

The Company PayPal has been revolutionizing commerce globally for more than 25 years. Creating innovative experiences that make moving money, selling, and shopping simple, personalized, and secure, PayPal empowers consumers and businesses in approximately 200 markets to join and thrive in the global economy. We operate a global, two-sided network at scale that connects hundreds of millions of merchants and consumers. We help merchants and consumers connect, transact, and complete payments, whether they are online or in person. PayPal is more than a connection to third-party payment networks. We provide proprietary payment solutions accepted by merchants that enable the completion of payments on our platform on behalf of our customers. We offer our customers the flexibility to use their accounts to purchase and receive payments for goods and services, as well as the ability to transfer and withdraw funds. We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account balance, PayPal and Venmo branded credit products, a credit card, a debit card, certain cryptocurrencies, or other stored value products such as gift cards, and eligible credit card rewards. Our PayPal, Venmo, and Xoom products also make it safer and simpler for friends and family to transfer funds to each other. We offer merchants an end-to-end payments solution that provides authorization and settlement capabilities, as well as instant access to funds and payouts. We also help merchants connect with their customers, process exchanges and returns, and manage risk. We enable consumers to engage in cross-border shopping and merchants to extend their global reach while reducing the complexity and friction involved in enabling cross-border trade. Our beliefs are the foundation for how we conduct business every day. We live each day guided by our core values of Inclusion, Innovation, Collaboration, and Wellness. Together, our values ensure that we work together as one global team with our customers at the center of everything we do – and they push us to ensure we take care of ourselves, each other, and our communities.

Job Summary

This job uses their knowledge and direction to influence decisions as an advisor or counsel, establishing overall business or technical strategy for the organization. They spend significant time on strategy and influencing decision‑making at the executive level.

Job Description

• 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

Subsidiary: PayPal Travel Percent: 0 - The base pay for this role will depend on where you work and the relevant experience and expertise you bring.

Pay Range

• Primary Location|Pay Range: SanJose, California: ($159,500.00-$236,500.00Annually)
• Additional Location(s)|Pay Range: Chicago, Illinois: ($145,000.00-$215,050.00Annually)

Additional compensation for this role may include an annual performance bonus, equity, or other incentive compensation, as applicable.

Hybrid Work Model

For the majority of employees, 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, ensuring that you equally have the benefits and conveniences of both locations.

Benefits

At PayPal, we’re committed to building an equitable and inclusive global economy. That’s why we offer comprehensive, choice-based programs, to support all aspects of personal wellbeing—physical, emotional, and financial—delivering meaningful value where it matters most. We strive to create a flexible, balanced work culture with a holistic approach to benefits, including generous paid time off, healthcare coverage for you and your family, and resources to create financial security and support your mental health.

Recruitment Process

PayPal does not charge candidates any fees for courses, applications, resume reviews, interviews, background checks, or onboarding. When making an application directly, we will never ask you to share passwords, one‑time passcodes (OTP), or verification codes. All communication regarding your application will come from official PayPal email domains.

Commitment to Diversity and Inclusion

PayPal provides equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, pregnancy, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state, or local law. In addition, PayPal will provide reasonable accommodations for qualified individuals with disabilities. If you are unable to submit an application because of incompatible assistive technology or a disability, please contact us at [e-mail].

Belonging at PayPal

Belonging at PayPal: Our employees are central to advancing our mission, and we strive to create an environment where everyone can do their best work with a sense of purpose and belonging. Belonging at PayPal means creating a workplace with a sense of acceptance and security where all employees feel included and valued. We are proud to have a diverse workforce reflective of the merchants, consumers, and communities that we serve, and we continue to take tangible actions to cultivate inclusivity and belonging at PayPal.

General Information

PayPal is on a mission to revolutionize commerce globally. We’re driving our company, industry, and society forward with vision and velocity. With our commitment to excellence, innovation, and talent, the possibilities are limitless. Learn more at PayPal.com/Jobs. Learn more about privacy-related questions or data retention. If you would like your profile to be deleted from our system, please let us know.