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.

-End of Document-

Who We Are

Checksum.ai is a high-growth, startup revolutionizing software testing with AI-powered, self-healing QA automation. We are backed by start up studio super{set} whose co-founders have over $1B in exits including Microsoft and Salesforce. 

We are a leading AI solution for software quality.  Checksum is growing fast, well funded and seeing massive demand for our solutions.  We are experiencing dramatic revenue growth.  This is an opportunity to join at the ground floor and scale up with us.

Checksum’s AI agents solve a critical problem for engineering teams who need to test their code fast and release high quality products.  AI coding tools have increased engineering output 50X, but quality has not kept up.  We fix that problem.

Checksum’s unique AI Agents deliver autonomous and continuous testing to engineering teams who need to build quality into their processes. No other testing tool or homegrown AI effort has the capabilities of our purpose-built testing models.

This is a hybrid role based out of our San Francisco Office 4x a week

What You’ll Do

• Drive positive outcomes for our top customers. Work internally and externally to do what it takes to make them successful​
• Own onboarding, work with Customer Engineering team on implementation, and drive adoption
• ​Ensure renewals, healthy accounts, prevent churn & reduce risk, help uncover expansion opportunities
• Build and maintain strong stakeholder relationships, leading QBRs, periodic update calls and support
• Be the voice of your book of business by synthesizing customer feedback and partnering closely with Product and Engineering to translate insights into actionable roadmap priorities
• Build playbooks for adoption and customer lifecycle based on experience

Who You Are

• Technically savvy, have the technical depth to communicate easily with Customer Engineering and understanding of the Checksum product
• Be a people person, have the ability to build strong relationships with your team and customer stakeholders
• Strong communicator, listens, empathetic, has business acumen, can interact with senior execs comfortably​
• Metrics driven, organized, good project skills, multi-tasking​
• Basic sales skills, can relay business value and present decks, product or other information​

What We Offer

• Competitive OTE: Equity + Benefits
• Be a key player in an early-stage startup with significant upside.
• Strong inbound pipeline – You won’t be starting from scratch.
• Catered lunch 5 days a week in our San Francisco office (hybrid flexibility available).
• A fast-moving, collaborative team that values execution over ego.
• Monthly Happy Hours 

About Checksum

We are a leading AI solution for software quality.  Checksum is growing fast, well funded and seeing huge demand for our solutions.  This is an opportunity to join at the ground floor and scale up with us.

Checksum’s AI agents solve a critical problem for engineering teams who need to test their code fast and release high quality products.  AI coding tools have increased engineering output 50X, but quality has not kept up.  We fix that problem.

Checksum’s unique AI Agents deliver autonomous and continuous testing to engineering teams who need to build quality into their processes. No other testing tool or homegrown AI effort has the capabilities of our purpose-built testing models.

Why Join Checksum?

✅ Explosive Growth – 10x ARR in the past year, selling into a booming market and sell into a greenfield territory.

✅ Cutting-Edge AI – Work with leading engineering teams adopting AI/ML-driven DevOps solutions.

✅ High Impact – Work directly with our co-founder and leadership to shape GTM strategy.

✅ Well-Funded & Backed by Experts – Supported by Super{Set}, a top-tier startup studio with multiple successful exits.

This is a hybrid position based in our San Francisco office 3x a week.

What You’ll Do

• Drive new revenue by actively prospecting, securing meetings, and closing business with key decision-makers across a green field territory of mid-market and enterprise accounts.
• Build and expand awareness of Checksum within target accounts and territories, identifying high-value opportunities for engagement and growth.
• Navigate complex, multi-stakeholder sales cycles, understanding customer budgets, procurement paths, and decision-making dynamics.
• Demonstrate a strong understanding of customer requirements related to AI development and quality assurance, and how the Checksum platform addresses those needs.
• Identify compelling pain points and use cases driving prospects to take action, and articulate the case for choosing Checksum
• Consistently achieve pipeline and revenue targets set by the company.
• Operate autonomously with focus, ownership, and strong execution discipline.
• Collaborate as a high-impact team player, contributing beyond your core responsibilities to support overall company success.
• Work 3 days per week in our San Francisco office to learn and grow as a team, unless visiting customers.

Who You Are

• Minimum 5+ years of outside sales experience to mid-market or enterprise accounts
• Proven success generating outbound leads and closing sales
• Experience selling developer tools, QA tools or related engineering solutions
• Experience selling to Heads of Engineering, developers, QA teams and C-level executives within engineering organizations 
• Ability to articulate and sell business value 
• Significant experience at a fast-paced startup and ability to work well in changing environments
• Experience identifying high-value customers and verticals to pursue
• Proven negotiation and closing skills
• Proficient in cloud and on-premise enterprise technology solutions

What We Offer

• Competitive OTE: $250k-$300K.
• Equity – Be a key player in an early-stage startup with significant upside.
• Catered lunch 5 days a week in our San Francisco office (hybrid flexibility available).
• A fast-moving, collaborative team that values execution over ego.
• Monthly happy hour and other team bonding opportunities. 

🚀 Join us in shaping the future of AI-powered software testing! If you're a top-performing AE ready to sell an innovative product, work closely with founders, and help build a world-class sales organization, we want to hear from you.

Apply today!

The estimated OTE $225K-$275K, with uncapped commission. This does not include the value of benefits or a potential equity grant. A wide range of factors are considered in making compensation decisions, including but not limited to skill sets, market conditions, experience and training, licensure and certifications, and business and organizational needs.