Chief of Staff, SMB & Financial Services Product

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 Chief of Staff for SMB & Financial Services Product is a senior strategic partner to the SVP, driving alignment, execution, and effective decision-making across a complex, product-led organization. Operating at the intersection of product strategy, business operations, and leadership, this role translates executive priorities into focused initiatives, aligned objectives, and measurable outcomes.

Acting as a force multiplier, the Chief of Staff supports executive-level thinking through rigorous analysis, synthesis of complex inputs, and preparation for critical leadership and board-level discussions. The role owns the operating rhythm, enables OKR alignment and follow-through, and strengthens cross-functional partnership—particularly with Go-To-Market and Commercial teams—while keeping the organization focused on customer-driven outcomes.

Job Description:

Essential Responsibilities:

• Establish overall business or technical strategy for the business operations of aligned organization.
• Influence decisions as an advisor or counsel to business leadership.
• Drive strategic objectives and ensure resources are effectively allocated.
• Provide oversight and support for planning and management of financial, budget, and headcount targets.
• Act as a liaison between business leadership, staff, and other key partners.
• Optimize workflows and drive process improvements to enhance organizational performance.
• Drive and monitor Objectives and Key Results (OKRs) to address gaps in business and operations.

Expected Qualifications:

• 10+ years relevant experience and a Bachelor’s degree OR Any equivalent combination of education and experience.

Additional Responsibilities & Preferred Qualifications:

Additional Responsibilities

• Serve as a strategic thought partner to the SVP, SMB & Financial Services Product, supporting enterprise-level decision-making through analysis, insight generation, and scenario development
• Own the Voice of Customer program for the product organization, ensuring customer insights, feedback, and data consistently inform product strategy, prioritization, and decision-making
• Support translation of product and business strategy into actionable initiatives and aligned OKRs, ensuring clarity, focus, and execution across the organization in partnership with PMO and functional leaders
• Own the leadership operating rhythm, including operating reviews, staff meetings, and executive forums that drive focus, accountability, and follow-through
• Lead preparation for executive reviews, and senior leadership forums, including narrative development, materials, and strategic recommendations
• Develop and maintain a deep understanding of the SMB and financial services landscape, including competitive dynamics, industry trends, and emerging risks and opportunities
• Proactively identify strategic blind spots, risks, and trade-offs across the portfolio, surfacing insights and recommendations with a strong bias toward action
• Enable and advance high-impact, cross-functional initiatives that require senior sponsorship, strategic judgment, and influence without direct authority
• Build strong, trust-based partnerships with Go-To-Market and Commercial leaders, ensuring tight alignment between product strategy, customer needs, and market execution
• Act as an extension of the SVP in select forums, representing leadership intent and facilitating alignment across Product, Engineering, Finance, and Commercial partners
• Partner closely with People, Finance, and Workforce Strategy teams on strategic workforce planning and talent priorities, while maintaining a high bar for leadership quality and hiring decisions
• Support senior-level hiring by shaping role definition, assessing talent against strategic needs, and ensuring strong onboarding and integration for new leaders
• Shape and drive leadership communications and change narratives to ensure clarity and consistency during periods of growth or transformation
• Plan and facilitate leadership offsites and strategy sessions that strengthen alignment and advance long-term priorities

Preferred Qualifications

• MBA or advanced degree
• Experience in financial services, payments, fintech, or adjacent regulated industries
• Background in management consulting, corporate strategy, investment banking, or similarly strategy-intensive environments
• Prior experience as a Chief of Staff or senior business operations leader in a product-led organization
• Demonstrated success influencing senior executives and cross-functional leaders without direct authority
• Experience supporting SVP- or C-level leaders in strategy, planning, or transformation roles
• Strong executive communication skills, including development of board-level and senior leadership presentations
• Proficiency with collaboration and planning tools such as Google Workspace, Slack, Confluence, and Jira

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:

San Jose, California | ($159,500.00 - $236,500.00 Annually)

Additional Location(s) | Pay Range:

No other locations are assigned to this requisition currently.Additional compensation for this role may include an annual performance bonus, equity, or other incentive compensation, as applicable. 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. For more information visit https://www.paypalbenefits.com.

PayPal does not charge candidates any fees for courses, applications, resume reviews, interviews, background checks, or onboarding. Any such request is a red flag and likely part of a scam. 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 benefits to help you thrive in every stage of life. We champion your financial, physical, and mental health by offering valuable benefits and resources to help you care for the whole you.

We have great benefits including a flexible work environment, employee shares options, health and life insurance and more. To learn more about our benefits please visit https://www.paypalbenefits.com.

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 paypalglobaltalentacquisition@paypal.com.

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.