Head of US Onboarding 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 own US seller onboarding operations across first-party and vendor-supported delivery motions. Reporting to the Head of Global Onboarding Operations, this leader will translate global onboarding strategy into US operating plans, manage multiple teams and workstreams, and drive measurable improvements in seller activation, time-to-value, service quality, workforce productivity, and cost-to-serve.

This role requires broad operational expertise, strong cross-functional influence, and the ability to make high-quality decisions in ambiguous situations. The right candidate can operate independently on significant assignments, build scalable operating mechanisms, and manage leaders responsible for day-to-day execution across a large and complex market.

What You Will Own

US Onboarding Operations

• Own US onboarding execution from post-sale handoff through go-live across applicable seller segments, channels, and delivery models.
• Establish operational objectives, work plans, staffing models, and performance requirements for US first-party and vendor-supported teams.
• Manage coverage, scheduling, routing, utilization, quality, escalations, and service-level adherence across US operations.
• Drive accountability for US market performance while implementing global onboarding standards and operating cadences.

Operational Excellence and Performance

• Improve key metrics including activation, time-to-value, CSAT, SLA adherence, utilization, and cost-to-serve.
• Use data, frontline insights, and business reviews to identify risks, root causes, and improvement opportunities.
• Lead process redesign, tooling improvements, automation opportunities, and playbook development for US onboarding workflows.
• Utilize AI to enhance seller outcomes and improve internal workflows

Cross-Functional Leadership

• Partner with Sales, Product, Finance, and regional GTM teams to improve seller onboarding outcomes.
• Influence senior stakeholders on priorities, tradeoffs, resource needs, and operational changes affecting US onboarding.
• Represent US onboarding operations in cross-functional forums and translate operational data into clear recommendations.

Team Leadership

• Manage multiple teams, managers, or workstreams within US onboarding operations.
• Coach and develop operational leaders, raising the bar for judgment, execution, accountability, and seller empathy.
• Build a culture of ownership, continuous improvement, and high-quality service delivery across distributed teams.

What We Are Looking For

• 12+ years of progressive operations leadership experience, ideally in technology, fintech, commerce, SaaS implementation, customer success operations, field operations, or scaled services delivery.
• Experience managing multiple teams or departments with responsibility for staffing, quality, cost, and performance.
• Strong understanding of workforce planning, capacity management, service delivery operations, and performance management.
• Experience leading through subordinate managers and influencing senior cross-functional stakeholders.
• Strong analytical and financial acumen, including KPI management, budget inputs, forecasting, and cost-to-serve improvement.
• Ability to operate independently in ambiguous situations while aligning with senior leadership on objectives and outcomes.
• Experience with vendor-supported operations, field teams, remote onboarding, or blended delivery models preferred.
• Clear communication, strong judgment, and the ability to gain alignment in sensitive or complex situations.
• 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.