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