Sr Director, Content Design Platforms + Systems

PayPal • San Jose, CA

4d • $218,000 - $323,950 • Hybrid

About The Position

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: As Senior Director, Content Design Platforms + Systems, you’ll lead a dual mission: 1. Elevate craft and quality immediately across our consumer and merchant experiences. 2. Build the next-generation Content Design Platform — the systems, frameworks, and intelligent tools that shape how PayPal communicates across products, surfaces, and agents. Job Description: Essential Responsibilities: Develop and articulate a clear, compelling vision and strategy in alignment with the content design strategy and operations that inspires others Oversee and direct the development of content design that enhances the user experience 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 and plans for content and design processes using domain knowledge and extensive expertise Provide guidance to critical cross-functional and cross-organizational teams focused on product transformation across PayPal Identify and resolve strategic problems or issues by developing new or innovative content design solutions Expected Qualifications: 12+ years relevant experience and a Bachelor’s degree OR Any equivalent combination of education and experience. Additional Responsibilities & Preferred Qualifications: PayPal is re-architecting how people experience money, commerce, and trust — and design sits at the center of that reinvention. We’re now evolving our content design discipline for the AI-native era. As Senior Director, Content Design Platforms + Systems, you’ll lead a dual mission: 1. Elevate craft and quality immediately across our consumer and merchant experiences. 2. Build the next-generation Content Design Platform — the systems, frameworks, and intelligent tools that shape how PayPal communicates across products, surfaces, and agents. You’ll report directly to the VP Platforms + Tools and partner closely with Design Systems, Research, and AI Foundations teams to define the language layer of our Design OS. This isn’t a copy or UX-writing leadership role. It’s a systems and transformation charter — defining how language, tone, and meaning function as part of intelligent products. What You’ll Lead Design the System Architect and scale the Content Design Platform — frameworks for tone, semantics, clarity, and trust integrated into our Design System and AI workflows. Define metrics for clarity, comprehension, and readability that become part of our Experience Quality Score. Partner with Design Systems and AI Foundations to create AI-assisted authoring and tone-evaluation capabilities. Elevate Craft Reset the content bar across all BUs: clarity, hierarchy, and human tone that embody PayPal’s new product language. Establish a company-wide clarity rubric and launch a cadence of content craft reviews, audits, and critiques. Mentor and calibrate content designers, creating a unified discipline identity and community of practice. Lead Transformation Rebuild the discipline’s reputation from tactical service to strategic design function. Drive the integration of content design into early product shaping, not just late-stage copy. Partner with design, product, and engineering leaders to embed clarity and meaning in every surface. What You’ll Bring 15+ years leading content design, UX writing, or language systems in product-led tech companies; 5+ years managing managers or large cross-disciplinary teams. Deep fluency in systems thinking — designing frameworks that scale, not just guidelines. Demonstrated experience working with or integrating AI-assisted design, LLMs, or data-informed authoring. Proven record of raising craft bar and discipline maturity in low-maturity environments. Ability to translate complex financial or technical concepts into clear, human language. Strong leadership presence: can influence executives and inspire practitioners alike. Equal comfort in a design critique, a system architecture review, or a CEO staff meeting. Why This Role This is a rare opportunity to define a discipline, not inherit one. You’ll help write the playbook for how language, design, and intelligence converge in digital experiences — and you’ll do it at a global scale. At PayPal, clarity is a competitive advantage. You’ll lead the team that builds it into the product — permanently. In the First 12 Months Deliver immediate uplift in craft and tone across flagship PayPal and Venmo experiences. Stand up the first version of the Content Design Platform inside our Design OS. Establish clarity and comprehension metrics integrated into our Design Impact Framework. Define the next generation of AI-assisted authoring and tone evaluation tools with our AI Foundations team. Build a high-performing team and guild culture that designers and writers aspire to join. Join Us We’re not just improving copy. We’re designing how PayPal — and AI — speak to the world.

Requirements

• 12+ years relevant experience and a Bachelor’s degree OR Any equivalent combination of education and experience.
• 15+ years leading content design, UX writing, or language systems in product-led tech companies; 5+ years managing managers or large cross-disciplinary teams.
• Deep fluency in systems thinking — designing frameworks that scale, not just guidelines.
• Demonstrated experience working with or integrating AI-assisted design, LLMs, or data-informed authoring.
• Proven record of raising craft bar and discipline maturity in low-maturity environments.
• Ability to translate complex financial or technical concepts into clear, human language.
• Strong leadership presence: can influence executives and inspire practitioners alike.
• Equal comfort in a design critique, a system architecture review, or a CEO staff meeting.

Responsibilities

• Develop and articulate a clear, compelling vision and strategy in alignment with the content design strategy and operations that inspires others
• Oversee and direct the development of content design that enhances the user experience 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 and plans for content and design processes using domain knowledge and extensive expertise
• Provide guidance to critical cross-functional and cross-organizational teams focused on product transformation across PayPal
• Identify and resolve strategic problems or issues by developing new or innovative content design solutions
• Architect and scale the Content Design Platform — frameworks for tone, semantics, clarity, and trust integrated into our Design System and AI workflows.
• Define metrics for clarity, comprehension, and readability that become part of our Experience Quality Score.
• Partner with Design Systems and AI Foundations to create AI-assisted authoring and tone-evaluation capabilities.
• Reset the content bar across all BUs: clarity, hierarchy, and human tone that embody PayPal’s new product language.
• Establish a company-wide clarity rubric and launch a cadence of content craft reviews, audits, and critiques.
• Mentor and calibrate content designers, creating a unified discipline identity and community of practice.
• Rebuild the discipline’s reputation from tactical service to strategic design function.
• Drive the integration of content design into early product shaping, not just late-stage copy.
• Partner with design, product, and engineering leaders to embed clarity and meaning in every surface.
• Deliver immediate uplift in craft and tone across flagship PayPal and Venmo experiences.
• Stand up the first version of the Content Design Platform inside our Design OS.
• Establish clarity and comprehension metrics integrated into our Design Impact Framework.
• Define the next generation of AI-assisted authoring and tone evaluation tools with our AI Foundations team.
• Build a high-performing team and guild culture that designers and writers aspire to join.

Benefits

• This role is also eligible for a range of benefits which may include, medical, dental, vision, life and disability insurance, parental and family leave, 401(k) savings plan, paid time off, and other benefits.
• We have great benefits including a flexible work environment, employee shares options, health and life insurance and more.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 5,001-10,000 employees