Head of Forward Deployed Engineering

Checksum is building AI that learns how software actually behaves and keeps it working. The Head of Forward Deployed Engineering will lead a team that works directly with customers to implement and scale Checksum’s AI, ensuring successful deployments that drive customer value and product insights.

Responsibilities:

• Lead end-to-end customer implementations: discovery, integration, deployment, and scale
• Build and operationalize AI-driven testing pipelines inside real production environments
• Reduce time from onboarding - value through strong scoping and execution discipline
• Own Proof of Concept and Proof of Value work with clear success criteria and outcomes
• Turn successful deployments into long-term adoption and expansion; you directly drive revenue and delivery
• Define clear success criteria, timelines, and measurable outcomes for every engagement
• Take on the most complex or high-stakes deployments yourself
• Build and lead a high-performing FDE team
• Hire engineers who can operate across product, customer, and systems
• Coach the team on how to navigate ambiguity, customer dynamics, and technical depth
• Set the quality bar for what gets shipped in customer environments
• Translate customer implementations into product insights and identify repeatable patterns across deployments
• Partner closely with the Co-Founder and engineering to turn patterns into product capabilities
• Help define where the line sits between custom work and core platform
• Work across customer stakeholders (engineering, QA, product, leadership) to align on outcomes, trade-offs, and timelines
• Partner closely with sales, product, and engineering to navigate ambiguity and drive decisions in high-stakes situations
• Handle real-world friction: conflicting priorities, unclear requirements, and evolving scopes
• Establish disciplined approaches to scoping, delivery, and tracking outcomes across engagements
• Define how Forward Deployed Engineering operates at Checksum
• Establish standards for implementation, code quality, and testing reliability
• Document what works, what fails, and what scales
• Create repeatable approaches that reduce reinvention across customers
• Ensure projects are predictable, not just successful
• Write, review, and debug code in JavaScript and TypeScript
• Build and evolve end-to-end test automation systems (Playwright or similar)
• Solve edge cases in CI/CD pipelines, environments, and test reliability