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WatershedWatershedNew York, NY

Head of Customer Operations

Lead strategy and operations for Watershed's Customer organization (CS, Advisory, Support). Own operating model, forecasting, AI-first workflows, data infrastructure, and team leadership to drive retention, expansion, and operational excellence.

200k – 245k/yr
On-site10+ YOERevenue Operations

About the role

Responsibilities

  • Partner with the Head of Customer and leadership to design the Customer org's operating model: org design, segmentation, engagement models, capacity and headcount planning, targets, P&L, performance frameworks, and incentives.
  • Own retention, expansion, and capacity forecasting end-to-end: methodology, models, and discipline that leadership and the Board trust.
  • Run the Customer operating rhythm: OKRs, business reviews, budgeting, long-range planning, forecast reviews, customer performance reviews, and QBRs.
  • Set the AI and technology strategy for the Customer org. Ship AI-first workflows, tooling, and enablement.
  • Build the data infrastructure that gives leadership real-time visibility into retention, expansion, adoption, service quality, health, and team performance.
  • Drive operational excellence: design, implement, and optimize customer-lifecycle processes and systems (post-sale handoffs, onboarding, expansion motions, renewal cycles, service quality, escalation processes).
  • Own the Customer org's systems strategy: evaluate build vs. buy, integrate CRM, CS platforms, Support tooling, and product data into one operating stack.
  • Build and lead the Customer Operations team: hire, develop, and set the bar for excellence.
  • Drive cross-functional alignment across Customer, Product, Sales, Finance, and Data.

Requirements

  • 10+ years of inside customer-facing GTM experience in high-growth B2B SaaS or AI, including experience leading operations teams responsible for the end-to-end customer journey.
  • 5+ years of direct management experience over teams of 3-6+; experience setting the bar, hiring, and developing operators.
  • Experience driving a technology-first rebuild of a customer operations function at scale.
  • Proven track record operationalizing retention and expansion motions, designing renewal programs, and building customer health systems.
  • Strong point of view on how AI will change Customer organizations; experience with Claude Code, Cursor, Clay, or similar is a plus.
  • Hands-on technical credibility with Salesforce (Flow, data model), SQL, and BI tools like Sigma.

Nice-to-Haves

  • Direct customer-facing leadership accountable for retention and expansion.
  • Experience building customer health scoring that drives strategic engagement.

Skills

SalesforceSQLSigmaCRMCustomer Success OperationsRetention ForecastingExpansion ForecastingOkr ManagementAi Workflow AutomationBI Tools

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