Director, Technical Programs

PayPal • San Jose, CA

1d • $178,500 - $291,500 • 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: The Principal Design Program Manager for Branded Checkout leads end-to-end program execution across PayPal's most complex, highly matrixed checkout experiences. This role requires exceptional ability to connect strategy to execution across Consumer, Merchant, Platform, and Partner organizations—navigating ambiguity and aligning stakeholders across Product, Engineering, Design, Marketing, Legal, Risk, and Compliance. You'll drive clarity in an environment where no single team owns the entire experience.

Requirements

• 10+ years relevant experience and a Bachelor’s degree OR Any equivalent combination of education and experience.
• Proven ability to manage large, complex engineering programs.

Nice To Haves

• 10+ years of program management experience in product/design organizations, with at least 5 years leading programs in highly matrixed, multi-stakeholder environments
• Proven track record managing end-to-end programs across distributed teams with no direct reporting relationships, demonstrating influence without authority
• Experience with payment systems, checkout flows, or similarly complex regulated product experiences involving multiple technical platforms and business constraints
• Demonstrated ability to operate at executive level—translating technical/design complexity into business impact and building credibility with VP+ stakeholders across functions
• Deep expertise in managing dependencies across 10+ teams simultaneously, anticipating integration challenges, and creating governance structures that drive accountability without bureaucracy
• Experience establishing program frameworks, rituals, and operating models from scratch in ambiguous environments

Responsibilities

• Develop and implement the strategic vision for engineering operational programs.
• Oversee the planning and execution of engineering programs.
• Ensure alignment of engineering programs with business goals.
• Manage and mentor program managers and engineering teams.
• Monitor program performance and drive continuous improvement.
• Communicate program status and strategic initiatives to executive leadership.
• Manage program budgets and financials.

Benefits

• 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.
• 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.
• 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.

What This Job Offers

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