Head of US Onboarding Operations

Bay Area, CA · US - CA - San Francisco City - Remote · USD 207,400-311,200 · 12+ years experience · Remote · Posted Oct 6, 2026

At a glance

Square is seeking a senior operations leader to oversee US seller onboarding operations across both first-party and vendor-supported delivery models.
The role involves translating global onboarding strategy into US operating plans, managing multiple teams, and driving improvements in seller activation, time-to-value, and service quality.

Own US onboarding execution from post-sale handoff through go-live across 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.
Drive accountability for US market performance while implementing global onboarding standards.
Improve key metrics including activation, time-to-value, CSAT, SLA adherence, utilization, and cost-to-serve.
Lead process redesign, tooling improvements, automation, and playbook development for US onboarding workflows.
Utilize AI to enhance seller outcomes and improve internal workflows.
Partner with Sales, Product, Finance, and regional GTM teams to improve onboarding outcomes.
Manage multiple teams, managers, or workstreams within US onboarding operations.
Coach and develop operational leaders to raise the bar for judgment, execution, and seller empathy.

12+ years of progressive operations leadership experience 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.
Clear communication, strong judgment, and the ability to gain alignment in sensitive or complex situations.
Experience improving workflows and customer outcomes using AI.