Head of Forward Deployed Engineering

superset} Hive Community•San Francisco, CA

7h•$170,000 - $225,000•Onsite

About The Position

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

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

Nice To Haves

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

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