Head of Forward Deployed Engineering

About the Company

Checksum is building AI that learns how software actually behaves and keeps it working. The hardest part is making that intelligence real inside messy, high-stakes production systems.

Responsibilities

• Lead end-to-end customer implementations including discovery, integration, and deployment
• Build and operationalize AI-driven testing pipelines inside production environments
• Build and lead a high-performing Forward Deployed Engineering team
• Translate customer implementations into product insights and repeatable patterns
• Partner with Co-Founders and engineering to turn field patterns into product capabilities
• Establish disciplined approaches to scoping, delivery, and tracking outcomes
• Write, review, and debug code in JavaScript and TypeScript
• Build and evolve end-to-end test automation systems

Requirements

• 8+ years building and shipping production software
• 4+ years leading engineers in fast-moving environments
• Strong coding ability in JavaScript and TypeScript
• Deep experience with CI/CD and test automation (unit, integration, E2E)
• Experience working directly with customers in technical contexts
• Ability to manage complex projects and drive execution against success metrics
• Strong understanding of system architecture, APIs, and modern dev workflows

Preferred Qualifications

• Experience with Playwright or modern E2E tooling
• Background in QA automation or quality engineering
• Experience in AI-first or agent-driven systems
• Experience building or scaling a solutions or forward deployed engineering function