Head of Forward Deployed Engineering

Checksum AI - San Francisco (In-Office)

checksum.ai

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.

• 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

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

• 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 turn into shipped outcomes
• A bias toward doing the work yourself, not delegating it

• Strong understanding of system architecture, APIs, and modern dev workflows
• Experience building or scaling test automation frameworks
• Comfort debugging real-world production issues under pressure

• 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 / forward deployed / customer engineering function

What you build, how you deploy, and what you learn in the field will directly determine:

• how fast we grow
• how strong the product becomes
• how much customers trust what we’ve built

• A defining role at an AI-first company at an inflection point
• Direct partnership with founders and core product decisions
• High ownership, minimal layers
• Competitive compensation and benefits
• Daily team lunches in-office