Head of Seller Onboarding External Workforce Operations

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

About the Role

Square is looking for a senior operations leader to define and manage the global external workforce and partner strategy for seller onboarding. Reporting to the Head of Global Onboarding Operations, this leader will own the operating model for third-party service providers, vendors, and BPO partners, ensuring that external delivery capacity improves seller outcomes while scaling efficiently and responsibly.

This role sits at the intersection of operations, workforce strategy, vendor governance, finance, procurement, legal, and regional execution. The right candidate can evaluate complex build-vs-buy tradeoffs, establish global partner standards, influence senior stakeholders, and create governance mechanisms that improve quality, cost, consistency, and scalability across markets.

What You Will Own

External Workforce Strategy

• Develop and maintain the global strategy for vendors, third-party service providers, and BPO partners supporting seller onboarding.
• Partner with regional operations leaders to determine the right labor mix by market, seller segment, service tier, and business need.
• Lead build-vs-buy analyses and recommend when work should be handled by first-party teams, vendors, BPO, partners, or self-serve models.
• Create scalable frameworks for external workforce footprint, capacity, quality, cost, and market coverage.

Partner Governance and Performance

• Establish global SLA frameworks, scorecards, quality standards, business review cadences, and escalation mechanisms for external partners.
• Hold vendors and BPO partners accountable for operational performance, seller experience, compliance with standards, and continuous improvement.
• Partner with Procurement, Legal, Finance, and regional teams on contracts, renewals, pricing structures, and commercial terms.

BPO and Vendor Operating Model

• Oversee the operating model for BPO and vendor-supported onboarding work, including role clarity, performance expectations, enablement, quality assurance, and escalation paths.
• Ensure partner operations are integrated with Square’s broader onboarding workflows, data, tooling, and seller experience standards.
• Identify opportunities to improve partner productivity, reduce cost-to-serve, and increase consistency across geographies.

Cross-Functional Leadership

• Influence senior leaders across Sales, Finance, Procurement, Legal, and regional teams.
• Translate external workforce performance and market needs into strategic recommendations for investment, partner selection, and operating model changes.
• Navigate sensitive partner and stakeholder situations while maintaining strong internal and external relationships.

Team Leadership

• Manage partner operations managers, BPO leaders, vendor managers, or related teams as the organization evolves.
• Develop leaders and build a culture of accountability, commercial rigor, operational discipline, and seller-focused execution.

What We Are Looking For

• 12+ years of progressive operations, vendor management, partner operations, BPO, procurement-adjacent, or workforce strategy experience.
• Deep experience managing third-party providers, BPOs, vendors, or outsourced service delivery at scale.
• Strong understanding of SLAs, partner governance, quality assurance, operational scorecards, and business review mechanisms.
• Experience making build-vs-buy recommendations and managing tradeoffs across quality, cost, speed, scalability, and risk.
• Strong financial and analytical acumen, including cost modeling, vendor spend management, ROI analysis, and capacity planning.
• Ability to influence senior stakeholders across several functional areas and gain alignment in complex or sensitive situations.
• Experience in fintech, commerce, SaaS implementation, customer operations, field services, or scaled services delivery preferred.
• Clear communication, strong judgment, and comfort operating independently on significant strategic assignments.
• Experience improving workflows and customer outcomes using AI

Why This Role Matters

Seller onboarding is one of the most important moments in the Square journey. The speed, quality, and consistency of a seller’s first experience directly shape activation, retention, satisfaction, and long-term value. This role helps ensure Square can scale onboarding globally while improving seller outcomes and operating efficiency.

We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we're doing to build a workplace that is fair and square? Check out our I+D page.