Head of Forward Deployed Engineering

Checksum AI - San Francisco (In-Office)

checksum.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.

What You’ll Own

Customer Delivery

• 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
  
  

Your accountability: customers getting real, durable value from the product

The Forward Deployed Engineering Function

• 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
  
  

Product Feedback Loop

• 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
  
  

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

Technical Depth

• 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
  
  

Nice to Have

• 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
  
  

Why This Role Matters

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
  
  

What You Get

• 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
  
  

Compensation

Competitive salary ($170K – $225K) plus generous founding stage equity. We’ll find the right package for the right person.

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