Senior Director - Experience Design, Checkout

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:

The Senior Director, Experience Design - Checkout will lead the design vision, strategy, and execution for PayPal's checkout experiences, shaping how consumers move through complex payment flows from merchant experiences through completion. This leader will guide a team focused on optimizing and evolving experiences at scale, combining strong design craft with experimentation, iteration, and systems thinking. Partnering closely with Product and Engineering, this role will shape roadmaps and outcomes, strengthen design standards and governance, and build a culture where designers effectively advocate for the customer while delivering simple, intuitive, and high-quality checkout experiences.

Job Description:

Essential Responsibilities:

• Develop and articulate a clear, compelling vision and strategy in alignment with Experience Design strategy and operations that inspires others
• Oversee and direct the development of user interface plans with direct impact on PayPal revenue, expense, budget, and growth
• Negotiate with and influence the decision-making of senior internal and external executives and decision-makers
• Create operational and strategic objectives that enhance user and customer experiences using domain knowledge and extensive expertise
• Provide guidance to critical cross-functional and cross-organizational teams focused on experience design across PayPal
• Identify and resolve strategic user interface and interaction design with new or innovative solutions

Minimum Qualifications:

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

PayPal is going through a once-in-a-generation transformation, creating a significant opportunity for a Design leader to help shape the next generation of interactions and systems for how humans and agents experience the world. This is a race to establish a durable system for the next generation of commerce as technology organizations shift and functions are redefined. Checkout is the proof point for when theoretical experiences become transactions that must meet regulation and navigate identity, compliance, safety, and security. PayPal shaped the first generation of putting money on the internet; we expect to equally influence and shape the next. We are looking for a leader who can hold big ideas while working tactically and incrementally - building, learning, and adapting in a rapidly shifting environment. Anchoring in first principles for customers and their rising expectations of experiences is a design challenge that has not been solved yet, and we are at the forefront of working on what that means around the world.

Role Scope & Priorities:

• Influence and execute on an existing 3-year strategy and work with cross-functional partners to set a design direction for PayPal's checkout experiences, delivering within and beyond the strategy, with a focus on flows, handoffs, and orchestration through completion.

• Lead the optimization and evolution of existing experiences at scale, using experimentation, iteration, customer insight, and strong design judgment to improve outcomes.

• Lead design planning, prioritization, and execution in close partnership with Product and Engineering, translating customer, business, and technical needs into strong design outcomes.

• Strengthen design systems, governance, standards, and review mechanisms to improve consistency, quality, and scalability across teams and products.

• Strengthen the connection between the Checkout design team and the broader Experience Design organization, raising expectations for craft, quality, and design advocacy.

• Build and develop a high-performing design team that can operate effectively in ambiguity, challenge ideas constructively, and ship, learn, and iterate.

• Represent Design with senior stakeholders, using strong storytelling, partnership, and influence to shape priorities and outcomes.

Experience & Capabilities:

• Significant product/experience design leadership experience, including experience leading design teams and managers.

• Demonstrated experience optimizing complex, existing products or flows at scale through experimentation and iteration;

• Strong, current design craft and fluency with modern design tools, with the ability to engage directly in the work, review designs, and shape frameworks and solutions. The expectation is that we are all makers and in the work, knowing how to scale through your team and having foundational knowledge of how the work gets done.

• Experience working within and shaping design systems.

• Demonstrated experience building, scaling, or significantly improving design systems, governance models, or design review processes.

• Strong track record partnering with Product and Engineering while maintaining a clear design point of view and advocating effectively for customers and design quality.

• Ability to operate in ambiguity, make thoughtful tradeoffs, and combine high craft with a strong commitment to delivery.

• Exceptional storytelling, communication, stakeholder partnership, and executive influence skills.

• Experience designing checkout, commerce, payments, transactional flows, or similarly complex digital experiences strongly preferred.

• 10+ years design leadership experience strongly preferred.

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. The expected range of pay for this role by location is:

Primary Location | Pay Range:

New York City, New York: ($242,000.00 - $359,150.00 Annually)

Additional Location(s) | Pay Range:

Chicago, Illinois: ($220,000.00 - $326,700.00 Annually)
Austin, Texas: ($220,000.00 - $326,700.00 Annually)
San Jose, California: ($242,000.00 - $359,150.00 Annually)

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

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.  Any such request is a red flag and likely part of a scam. All communication regarding your application will come from official PayPal email domains. If you suspect fraudulent activity, please report it immediately.  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.