Head of Business Operations - Remote

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.

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. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same. 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 work streams, 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.

• 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.

• 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.
• Represent US onboarding operations in cross-functional forums and translate operational data into clear recommendations.
• Manage multiple teams, managers, or work streams within US onboarding operations.
• Build a culture of ownership, continuous improvement, and high-quality service delivery across distributed teams.

• 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.
• Strong analytical and financial acumen, including KPI management, budget inputs, forecasting, and cost-to-serve improvement.
• Experience with vendor-supported operations, field teams, remote onboarding, or blended delivery models preferred.
• Experience improving workflows and customer outcomes using AI.

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…