Head of Customer Success

About ContextQA

ContextQA is an AI-native software quality platform that helps engineering and QA teams ship faster with fewer bugs. By combining intelligent test generation, autonomous execution, and continuous quality insights, ContextQA removes the bottlenecks that slow down release cycles, so engineering leaders can focus on building, not firefighting.

The Opportunity

We are hiring our first US-based Head of Customer Success to own the post-sale relationship and make sure customers get real, measurable value from ContextQA, fast.

This is a foundational hire. Customer success at ContextQA runs through the founder and product team today. You will be the first dedicated US CS hire, which means you are not stepping into a playbook. You are building it. You will own onboarding, adoption, retention, and expansion, and define how ContextQA delivers customer outcomes as we scale.

This is a technical, hands-on role. Depending on the account, it carries elements of forward-deployed engineering. You may sit close to implementation, work directly in the product alongside the customer, and own technical adoption, not just relationship management.

You will work directly with the VP of Sales, AEs, the Solutions Engineering team, founder, and product engineering.

What You'll Own
The post-sale relationship for enterprise customers, from kickoff through onboarding, adoption, renewal, and expansion.
Structured onboarding. Define success criteria with the customer, build the adoption plan, drive time-to-value against clear milestones.
Hands-on, forward-deployed work in the product alongside customers on technical adoption and implementation where the account needs it.
Product adoption. Track usage against customer goals, identify where teams stall, intervene before adoption stalls.
Renewals and churn protection. Monitor account health, surface risk early, lead renewals from a position of demonstrated value.
Expansion. Partner with AEs on the path from core platform into AI agent testing and broader use across the customer's organization.
Voice of the customer internally. Capture patterns, feature gaps, and field feedback for product.
The reusable infrastructure of customer success: onboarding playbooks, success plan templates, health-scoring, QBR formats, adoption frameworks.

Required

10+ years in customer success, account management, technical account management, or post-sale roles in enterprise B2B SaaS, ideally in a technical product such as QA, test automation, DevOps, or developer tools.
Experience owning Fortune 500 and large-enterprise accounts, managing multiple stakeholders, executive relationships, and complex renewal and expansion cycles.
Track record owning onboarding, adoption, retention, and expansion, including renewal and net revenue retention.
Comfort working hands-on with a technical product and with technical buyers (QA leaders, engineering managers, DevOps teams), translating capability into business outcomes.
Working understanding of AI agentic testing, QA automation, AI/ML concepts, and the questions enterprises face moving agents into production.
Strong instincts for account health, able to spot churn risk and expansion signal early and act on both.
Excellent written communication: onboarding plans, QBRs, renewal recaps, follow-ups that keep accounts moving.
Self-directed and comfortable in an early-stage environment. You can build the CS function alongside us.
Bachelor's degree or equivalent professional experience.

Nice to Have

Background in QA, software engineering, SDET, or DevOps before moving into customer success.
Forward-deployed engineering experience at a seed, Series A, or high-growth startup.
Hands-on familiarity with AI agents, MCP workflows, or AI evaluation frameworks.
Experience with enterprise application environments: Salesforce, Workday, SAP, Oracle, ServiceNow.
Experience building CS playbooks, health-scoring, and onboarding frameworks from scratch.

Why Join ContextQA

First US CS hire. You define the function and report directly to the VP of Sales.
A category with genuine momentum: AI-native QA is changing how engineering teams ship software.
Competitive compensation with performance variable, meaningful early-stage equity (huge upside potential), and full benefits.
Flexible, remote-first culture with the autonomy to build the function your way.
Opportunity to grow into a CS leadership role as the function scales.