Head of Forward Deployed Engineering

ai The Role 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. You will lead Forward Deployed Engineering: a team that works directly with customers, builds inside their environments, and turns Checksum’s AI into something that delivers real, measurable outcomes.

This is a player-coach role. You will define how we deploy, implement, and scale our product in the field. You will set the bar for what “good” looks like.

You will take on the hardest implementations yourself. And the patterns you discover will shape the product. If you’re looking to manage from a distance, this is not the role for you.

Requirements

, and evolving scopes The Playbook 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 Staying Close to the Work 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 What Success Looks Like In the first 6-9 months: Customers are live faster and expanding usage A small, strong FDE team is in place and shipping consistently A clear, evolving playbook exists and is actively used Repeatable implementation patterns begin to emerge Product improves directly because of field insights Success Signal: better outcomes, delivered faster, with less reinvention each time What You Bring Must Have 8+ years building and shipping production software 4+ years leading engineers in fast-moving environments Strong coding ability in JavaScript / TypeScript Deep experience with CI/CD and test automation (unit - integration - E2E) Experience working directly with customers in technical contexts Strong ability to manage complex projects and drive execution against defined success metrics Ability to move from ambiguity to scoped solutions that work and