Sr Director, Enterprise Systems

PayPal • San Jose, CA

1d • $218,000 - $323,950 • Hybrid

About The Position

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: This job develops and articulates a compelling vision and strategy aligned with PayPal's objectives. They inspire teams to achieve long-term success in enterprise systems, collaborating with executive leadership to influence strategic decision-making. This role oversees the implementation and optimization of large-scale systems, ensuring alignment with business processes to enhance operational efficiency. As the Senior Director of Enterprise Systems, you will lead a large-scale global technology organization delivering critical enterprise platforms across HR, Legal and Employee Experience. You will oversee multiple functional domains spanning HR Systems, Employee Experience Technology and Legal Technology leading a global team across the US and APAC.

Requirements

• 12+ years relevant experience and a Bachelor’s degree OR Any equivalent combination of education and experience
• 15+ years in technology leadership roles, with at least 5 years managing organizations of 100+ people
• Deep expertise in enterprise systems (HR Tech, Legal Tech, FinTech, or Employee Experience platforms)
• Proven track record delivering large-scale transformation programs with direct impact on revenue, expense, and growth
• Experience managing globally distributed teams across multiple time zones and geographies
• Strong background in platform architecture, SaaS technologies, and cloud infrastructure
• Demonstrated ability to influence and negotiate with senior executives and decision-makers
• Visionary leadership: Ability to develop and articulate compelling long-term strategy that inspires teams
• Executive presence: Commands credibility with C-suite stakeholders and external partners
• Talent development: Track record of building high-performing teams and developing future leaders
• Strategic thinking: Translates business strategy into technology execution with PayPal-wide impact
• Change management: Leads organizations through transformation with empathy and clarity
• Organizational design: Optimizes structure, spans, and accountability frameworks
• Strong understanding of modern software engineering practices (Agile, DevOps, CI/CD)
• Knowledge of enterprise architecture patterns, integration technologies, APIs
• Familiarity with AI/ML applications in enterprise technology
• Understanding of security, compliance, and data governance requirements
• Experience with cloud platforms (AWS, GCP, Azure)
• P&L management and budget accountability with direct impact on PayPal's financial metrics
• Vendor negotiation and contract management at enterprise scale
• ROI analysis and business case development
• Understanding of HR, Legal, Finance business processes and their strategic importance to PayPal

Nice To Haves

• Prior experience with Workday, Salesforce, or similar enterprise platforms highly preferred

Responsibilities

• Develops and articulates a clear, compelling enterprise systems vision and strategy in alignment with PayPal-wide strategy and operations that inspires others
• Oversees and directs the creation of enterprise systems strategy across PayPal, with direct impact on PayPal revenue, expense, budget, and growth
• Negotiates with and influences the decision-making of senior internal and external executives and decision-makers
• Inspires group leaders and directors to cultivate a team environment where everyone can perform at their best and receive opportunities for development
• Build and develop talent to meet long-term business objectives and strategy
• Focused on the long-term success and strategy of enterprise systems
• Partner with C-suite executives (CHROs, General Counsel, CFO) to translate business needs into scalable technology solutions while driving platform modernization
• Establish architectural standards, technology roadmaps, and investment priorities aligned with PayPal's long-term objectives, making decisions that may have long-term effects on PayPal's success
• Build trusted partnerships with C-suite executives across HR, Legal, Finance, and Employee Experience organizations
• Lead vendor strategy and negotiations for enterprise platforms (Workday, Salesforce, etc.) at executive level
• Advocate for enterprise systems investments at executive forums and budget planning cycles while representing enterprise technology in cross-functional strategic initiatives
• Work with senior leaders to provide cohesive direction towards PayPal goals, serving as key advisor on complex business situations
• Drive organizational efficiency through span optimization, structural improvements, and clear roles, responsibilities, and decision rights across functional domains
• Foster culture of innovation, accountability, and continuous improvement across US, APAC, and other international operations
• Manage comprehensive talent pipeline and develop methods and techniques for how projects, programs, and people operate, creating lasting organizational capabilities
• Oversee the implementation and optimization of large-scale enterprise systems, ensuring alignment with business processes to enhance operational efficiency
• Ensure reliable operations of mission-critical enterprise systems (99.9%+ uptime) with established SLAs, KPIs, and operational metrics
• Drive incident management, problem resolution, and continuous service improvement while managing capacity planning and resource allocation
• Implement Agile/DevOps practices and engineering best practices across the organization
• Control activities across multiple areas with notable risk and complexity, leading resolution of highly complex or unique business situations
• Lead large-scale transformation programs across HR and Legal platforms with comprehensive program governance and stakeholder communication
• Drive adoption of emerging technologies (AI/ML, automation) to enhance operational efficiency and establish enterprise systems as strategic enabler
• Champion automation, self-service, and developer productivity initiatives while ensuring security, compliance, and data governance standards
• Anticipate factors that could impact strategy and PayPal's position in the marketplace
• Contribute results that lead to development of innovative strategies, services, or products

Benefits

• 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.
• generous paid time off
• healthcare coverage for you and your family
• resources to create financial security and support your mental health

What This Job Offers

• Job Type: Full-time
• Career Level: Executive