Director, Sales Enablement

PayPal
Chicago, IL

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 Description Summary:
The Director, Sales Enablement will establish measurable organizational goals and drive performance and results across the Americas region. This role will be a key part of the leadership team, developing long-range strategic plans to impact critical areas of PayPal’s sales function. The Director will ensure impactful sales enablement and learning strategies, directly influencing business outcomes through innovative approaches, and will regularly advise senior executives on decisions affecting the Americas market.

Job Description:
Essential Responsibilities:

  • Establish overall business or technical strategy for the organization with significant impact on PayPal operations.
  • Influence executive-level decision-making through strategic counsel and advisory.
  • Lead the development of initiatives that drive revenue and achieve sales targets.
  • Coordinate with various departments to ensure smooth communication and collaboration.
  • Oversee the preparation of sales presentations and management of CRM systems.

Expected Qualifications:

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

Additional Responsibilities and Preferred Qualifications
Key Responsibilities
  • Develop and implement long-term, measurable sales enablement strategies that support regional and company-wide objectives for the Americas.
  • Establish and maintain business or technical strategies with significant impact on operational success.
  • Lead the effort in resolving highly complex or unique business challenges and translate insights into operational and tactical plans.
  • Provide strategic direction and develop long-range plans for sales enablement, aligned with PayPal’s goals for the Americas.
  • Use expertise to influence key decisions at the executive level and act as an advisor or counsel within the organization.
  • Manage, mentor, and inspire a team of sales enablement leaders, building organizational capability across the Americas.
  • Partner with Sales Learning and Effectiveness leads in Europe and Asia Pacific to ensure aligned approach to sales delivery and impact metrics reported to leadership.

Required Skills And Experience
  • Demonstrated experience influencing executive-level decisions and shaping strategies with broad organizational impact.
  • Proven track record in developing innovative approaches, driving organizational success, and resolving complex sales challenges.
  • 10+ years of relevant experience with a Bachelor’s degree or equivalent combination of education and experience. MBA preferred.
  • Advanced analytics, executive communication, and business acumen skills required to guide senior leaders.
  • History of managing teams and functional areas, focused on strategy and execution at scale.
  • Significant expertise in sales enablement platforms, CRM tools, and modern sales training techniques.

PayPal is committed to fair and equitable compensation practices.

Actual Compensation is based on various factors including but not limited to work location, and relevant skills and experience.

The total compensation for this practice may include an annual performance bonus (or other incentive compensation, as applicable), equity, and medical, dental, vision, and other benefits. For more information, visit

The U.S. national annual pay range for this role is $152,500 to $262,350

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

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 benefits to help you thrive in every stage of life. We champion your financial, physical, and mental health by offering valuable benefits and resources to help you care for the whole you.

We have great benefits including a flexible work environment, employee shares options, health and life insurance and more. To learn more about our benefits please visit

Who We Are:

To learn more about our culture and community visit

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.

REQ ID R0132713
Posted 2025-11-12

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