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Head of Customer Success

🌐 Remote💼 Full-time🗓 2026-09-24

Core

Own the post-sale relationship for enterprise customers, driving onboarding, adoption, retention, and expansion to ensure measurable value from ContextQA's AI-native QA platform.

Role type

Head of Customer Success (Foundational, building the function from scratch)

Builds

Customer success infrastructure including playbooks, success plans, health-scoring, and QBR formats.

Domain

B2B SaaS, AI-native software quality, test automation, DevOps

Deliverable

production ML models | product features | dashboards & analysis | client delivery

Required skills

Enterprise B2B SaaS customer success leadership, Fortune 500 account management, onboarding and adoption strategy, churn risk identification, renewal and expansion execution, technical product adoption, stakeholder management, written communication, early-stage environment adaptability

Preferred skills

QA/DevOps background, forward-deployed engineering experience, AI agent testing familiarity, enterprise application environment experience

Technologies

Salesforce, Workday, SAP, Oracle, ServiceNow, AI agents, MCP workflows, AI evaluation frameworks

Responsibilities

Define and execute structured onboarding plans with success criteria, track usage and intervene to prevent adoption stalls, monitor account health and lead renewals, partner with AEs on expansion into AI agent testing, capture customer feedback for product, build reusable CS infrastructure

Seniority

Senior, hands-on IC (Foundational hire)

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