Senior Director, Experience Design - Checkout
About The Position
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. The role guides a team focused on optimizing and evolving experiences at scale through strong design craft, experimentation, iteration, and systems thinking. In close partnership with Product and Engineering, the leader will shape roadmaps and outcomes, strengthen design standards and governance, and foster a culture in which designers advocate for customers while delivering simple, intuitive, high-quality checkout experiences. This leader will help shape the next generation of interactions and systems for commerce, translating big ideas into tactical, incremental work in a rapidly changing environment. Checkout experiences must turn new concepts into transactions while addressing regulation, identity, compliance, safety, and security. The position will influence and execute an existing three-year strategy, lead the optimization of existing experiences, strengthen design systems and review mechanisms, and represent Design with senior stakeholders. It also includes building and developing a high-performing design team that can operate in ambiguity, ship, learn, and iterate.
Requirements
- 12 or more years of relevant experience and a Bachelor’s degree, or an equivalent combination of education and experience.
- Five years of experience leading others.
- Significant product or experience design leadership experience, including 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.
- 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 for customers and design quality.
- Ability to operate in ambiguity, make thoughtful tradeoffs, and combine high craft with commitment to delivery.
- Exceptional storytelling, communication, stakeholder partnership, and executive influence skills.
Nice To Haves
- Experience designing checkout, commerce, payments, transactional flows, or similarly complex digital experiences.
- Ten or more years of design leadership experience.
Responsibilities
- Develop and articulate a clear, compelling vision and strategy aligned with Experience Design strategy and operations.
- Oversee and direct the development of user interface plans with direct impact on PayPal revenue, expense, budget, and growth.
- Negotiate with and influence senior internal and external executives and decision-makers.
- Create operational and strategic objectives that enhance user and customer experiences.
- Guide critical cross-functional and cross-organizational teams focused on experience design across PayPal.
- Identify and resolve strategic user interface and interaction-design challenges with new or innovative solutions.
- Influence and execute the existing three-year strategy and work with cross-functional partners to set design direction for checkout experiences, focusing on flows, handoffs, and orchestration through completion.
- Lead optimization and evolution of existing experiences at scale using experimentation, iteration, customer insight, and design judgment.
- Lead design planning, prioritization, and execution in partnership with Product and Engineering, translating customer, business, and technical needs into design outcomes.
- Strengthen design systems, governance, standards, and review mechanisms to improve consistency, quality, and scalability.
- Strengthen the Checkout design team’s connection to the broader Experience Design organization and raise expectations for craft, quality, and design advocacy.
- Build and develop a high-performing design team that operates effectively in ambiguity, challenges ideas constructively, and ships, learns, and iterates.
- Represent Design with senior stakeholders through storytelling, partnership, and influence to shape priorities and outcomes.
- Engage directly in design work, review designs, and shape frameworks and solutions while scaling work through the team.
Benefits
- Generous paid time off.
- Healthcare coverage for employees and their families.
- Resources to support financial security and mental health.
- Annual performance bonus, equity, or other incentive compensation, as applicable.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
