Head of Forward Deployed Engineering

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

Compe…