Chief of Staff, SMB & Financial Services Product

PayPal • San Jose, CA

23h • Hybrid

About The Position

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.

Requirements

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

Nice To Haves

• 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

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.
• 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

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 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: Mid Level