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:

PayPal is seeking a senior commercial leader to direct sales strategy, advertiser acquisition, and revenue growth for PayPal Ads.

This role is responsible for leading a vertically aligned brand and agency sales organization, establishing scalable go-to-market motions, and driving sustainable revenue growth across enterprise advertisers. The Senior Director will ensure consistent commercial execution, strengthen PayPal’s position within the commerce and retail media landscape, and steward cross-functional alignment with product, marketing, finance, operations, and merchant teams.

The ideal candidate brings deep experience in digital advertising, commerce media, or retail media, with demonstrated success building and managing high-performing sales teams, influencing senior-level customer stakeholders, and developing repeatable commercial processes.

Job Description:

Essential Responsibilities:

• Lead national or global ad sales strategy and execution
• Oversee organizational design, talent development and performance management
• Build and maintain C-suite client relationships
• Partner with executive leadership on product, marketing and revenue strategy
• Represent ad sales in board-level and investor discussions

Minimum Qualifications:

• 12+ years of relevant experience and a Bachelor's degree OR Any equivalent combination of education and experience
• 5 years of experience leading others

Leadership and Team Management

• Lead, develop, and scale a high-performing sales organization, including brand-direct sellers, and agency-focused account executives.
• Establish operational rhythms, performance management practices, and capability development programs that ensure consistent and predictable execution.
• Foster a culture of accountability, collaboration, and continuous improvement

Commercial Strategy and Revenue Accountability

• Own revenue delivery for PayPal Ads; manage forecasting, pipeline development, quota attainment, and category planning.
• Develop and implement sales strategies that align with business objectives, advertiser needs, and market opportunities.

Go-to-Market Execution

• Lead the development of go-to-market materials, value propositions, sales enablement content, and commercial packaging for PayPal Ads solutions.
• Partner with Product, Marketing, and Operations teams to support launch readiness, roadmap clarity, and solution positioning.
• Ensure internal stakeholders have a clear understanding of platform capabilities, advertiser use cases, and recommended sales approaches.

Client and Agency Engagement

• Build and expand relationships with enterprise advertisers, media agencies, holding companies, and strategic partners.
• Serve as an executive-level point of escalation for key customer relationships.
• Guide teams in negotiating commercial terms, executing agreements, and maintaining high standards of customer satisfaction and retention.

Platform Adoption and Performance Management

• Oversee advertiser onboarding, campaign execution, and program optimization to ensure measurable results and long-term account growth.
• Promote data-driven insights, measurement capabilities, and attribution methodologies that reinforce the value of PayPal Ads solutions.
• Ensure operational consistency across sales, customer success, and product support functions.

Market and Industry Expertise

• Maintain comprehensive knowledge of digital advertising, commerce media, and retail media industry trends, including audience targeting, measurement, attribution, and competitive landscape.
• Provide internal leadership with insights into market dynamics, customer feedback, and opportunities for product or process enhancement.
• Represent PayPal Ads with professionalism in industry forums, customer engagements, and strategic partnership discussions.

Preferred Qualifications

• Bachelor’s degree required; advanced degree (e.g., MBA) preferred or equivalent work experience.
• 12–15+ years of experience in digital advertising, commerce media, retail media, or related fields, including leadership of multi-level sales or account management teams.
• Proven track record in brand-direct and agency sales, with strong familiarity navigating media holding companies, performance media teams, and retailer/commerce media buyers.
• Demonstrated experience driving revenue growth, developing commercial strategies, and building scalable GTM processes.
• Expertise with brand and pay-for-performance advertising models, data-driven targeting, or incentive-based offer platforms preferred.
• Strong negotiation skills with experience developing and executing complex commercial agreements.
• Exceptional communication, executive presence, and relationship management capabilities.
• High degree of business and financial acumen, including the ability to interpret data, develop insights, and guide strategic decisions.
• Ability to collaborate effectively in a matrixed global organization and influence cross-functional stakeholders.
• Results-oriented, self-directed, and capable of operating in a dynamic, evolving environment.
• Ability to travel as required for client meetings, internal alignment, and industry events.

Preferred Competencies

• Strategic thinking and commercial planning
• Organizational leadership and talent development
• Executive-level communication and influence
• Customer-centric decision-making
• Analytical problem solving and data fluency
• Operational discipline and process management
• Change leadership and adaptability

Subsidiary:

PayPal

Travel Percent:

0

-

The pay for this role will depend on where you work and the relevant experience and expertise you bring. The expected range of pay, including base pay and commission-based compensation, for this role by location is:

Primary Location | Pay Range:

New York City, New York | ($347,000.00 - $515,900.00 Annually)

Additional Location(s) | Pay Range:

Chicago, Illinois | ($316,000.00 - $468,600.00 Annually)

Details about the commission structure will be provided during the hiring process, consistent with applicable laws. Additional compensation for this role may include equity, or other incentive compensation, as applicable.

PayPal does not charge candidates any fees for courses, applications, resume reviews, interviews, background checks, or onboarding. Any such request is a red flag and likely part of a scam. To learn more about how to identify and avoid recruitment fraud please visit https://careers.pypl.com/contact-us.

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.

Our Benefits:

At PayPal, we’re committed to building an equitable and inclusive global economy. And we can’t do this without our most important asset-you. 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.

Who We Are:

Click Here to learn more about our culture and community.

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 [email protected].

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.

Any general requests for consideration of your skills, please Join our Talent Community.

We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates. Please don’t hesitate to apply.

Notice to Applicants and Employees who reside within New York City. Click here to view the notice.