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-

About Us:

super{set} is dedicated to founding, funding, and building data and AI-native startups. Led by  a team of serial AI founders with multiple exits, super{set} operates within a people-first culture, bringing hands-on support to its portfolio companies from ideation through exit..

We don’t just critique - we roll up our sleeves and partner with product-centric co-founders who bring grit, humility, and clock-speed. Together at the whiteboard,  we craft category-defining startups. Every company starts in-house, fully seed-funded by super{set}, before we invite outside investors at Series A.

This is a hybrid role, based in our SF office 4x a week.

ROLE
The Sr. Recruiter at super{set} is both strategist and doer - shaping our talent brand,  leading high-value searches (from co-founders to specialized engineers), and helping portfolio founders make their most critical hires.

In this hands-on role, you’ll work closely with super{set}’s partners and portfolio co-founders to anticipate business needs, build targeted pipelines, and drive end-to-end recruiting strategies. You’ll manage searches from sourcing to close across technical and business functions, and guide key stakeholders through the process. We hope you’re eager to experiment with creative approaches to attract rare talent.

RESPONSIBILITIES

• Design super{set}-side and company-specific recruiting strategy for attracting exceptional talent
• Run full-cycle talent searches for super{set} portfolio across engineering, product and GTM
• Source and engage high-caliber talent using targeted outreach, referrals, and market mapping
• Drive tight hiring processes, ensuring strong calibration, fast feedback loops, and decisive outcomes to raise the hiring bar
• Track pipeline health and recruiting metrics; optimize for speed, quality, and close rate
• Independently test and own talent positioning and messaging, iterating rapidly based on response
• Ensure that we are constantly aware of and responsive to talent market shifts in compensation, availability, and competitor movement

WHAT YOU’LL BRING

• 5–8 years experience, ideally as the first recruiting lead at an early-stage startup
• Proven ability to run highly specialized, search-oriented recruiting efforts for hard-to-find, high-value roles, from early tenure engineering roles to senior CXO level hires
• Strong talent network and credibility within the engineering, product and GTM community
• Excellent communication skills and ability to influence people at all levels in the organization
• A “doer” mentality with the ability to translate vision into action, and a strong growth mindset

CREDENTIALS

• High-energy, proactive, and thrives on hustle
• Confident, credible, able to hold their own in conversations with highly technical or entrepreneurial talent
• Naturally extroverted and eager to build new connections, including in unconventional spaces and with harder-to-reach technical talent
• Structured, data-driven, and creative problem solver
• Comfortable with ambiguity, fast learner, prefers experimentation over stringent playbooks
• Collaborative, ability to influence stakeholders across all organizational levels and challenge constructively

WHAT WE OFFER

• A rare opportunity to shape 10+ startups from inception, in parallel
• Central role working directly with entire super{set} team and portfolio leadership
• Gain inside access to company formation, and build a career path toward founding, VC, or scaling leadership
• Competitive compensation package, including salary and meaningful equity

The Role

Kana is an agentic AI platform for marketers. We help enterprise brands find better audiences, optimize campaigns, and stay visible in an AI-driven world — using synthetic data enrichment, AI-powered analytics, and answer engine optimization.

We’re building a team of AI Solutions Builders — people who work directly with enterprise customers and use AI coding agents to build the applications that solve their problems. This role leads that team of AI Solutions Engineers, setting standards and taking on the most complex builds. This team is a key input into our product strategy as the patterns you identify and the systems you design will directly shape Kana’s core platform.

This is a player-coach position. You’ll define the playbook for how we build software with AI, set the quality bar for what ships, and manage a growing team of builders. But you’ll also be hands-on — taking customer engagements yourself, building applications with AI tools, and staying deep in the work. If you’re looking for a role where you manage from a distance, this isn’t it.

We want someone with a product management background in adtech or martech who understands how consumer-facing brands think about audiences, campaigns, and growth. You’ve been technical your whole career — not necessarily an engineer, but someone who reads code, understands systems, and has strong opinions about how things should be built.

You’ll report directly to the co-founder/CTO.

Hybrid - 4 days/week

What You’ll Own

Customer Delivery

• Deliver high-quality marketing applications that customers rely on in production. Lead enterprise engagements end-to-end: discovery, requirements, build, and delivery of marketing applications on Kana’s platform.
  • Reduce time from discovery to live deployment through disciplined scoping and AI-assisted workflows.
  • Identify repeatable patterns across customer builds and partner with engineering to turn them into scalable features.
• Take on the most complex or high-stakes customer builds yourself. Set the standard for what good looks like.
• Ensure every application your team ships meets enterprise quality standards — performance, reliability, UX.

Team

• Hire, develop, and manage a team of AI Solutions Builders (starting small, growing with as the company grows).
• Coach the team on how to get the best output from AI coding agents, how to review generated code, and how to work with enterprise customers.
• Create the feedback loops between your team and the platform engineering team so tool improvements compound.

Product Strategy for the Solutions Practice

• You will synthesize insights from customer builds and work closely with the CTO and platform team to determine which capabilities should become first-class products.
• Define the product strategy for the solutions practice: what types of applications we build, how we scope engagements, and where we draw the line between custom builds and platform capabilities.
• Identify patterns across customer engagements that should become repeatable products or templates.
• Shape the roadmap for our AI-assisted development tooling based on what you see working (and failing) in the field.

The Playbook

• Define and evolve the playbook for AI-assisted application development: which tools to use, how to structure prompts, code review standards, quality benchmarks for AI-generated output, how to handle edge cases.
• Document what works, what doesn’t, and which approaches produce the best outcomes for different types of applications.
• Stay on top of the rapidly evolving AI tooling landscape and integrate new capabilities as they emerge where they materially improve speed or reliability.

What Success Looks Like

This is a new team, so we’re not handing you a rigid scorecard. But in 6–9 months, we’d expect to see a small high-performing team in place and consistently shipping customer applications. A documented playbook that’s being used actively, tested and refined through real engagements, and early signs of repeatable patterns: the kinds of applications and approaches that work well enough to become starting points rather than blank slates. The clearest signal of success is that customers are getting better applications, faster, and your team is getting measurably better at building them.

What We’re Looking For

Must Have

• Product management or customer facing product engineering background in adtech or martech. You understand how consumer brands think about audience targeting, campaign optimization, and growth — because you’ve built products in that world.
• Technical depth. You can read Python, React, and SQL. You understand API design, data modeling, and system architecture. You’re the PM who engineers actually want to work with because you speak their language.
• Hands-on experience building real applications using AI coding tools (Claude Code, Cursor, Copilot, or similar). You’ve built real things with them and have strong opinions about how to get the best results. You understand both their leverage and their limitations.
• Experience leading small teams in a startup or high-growth environment. You know how to hire well, set a high bar, and develop people — without layers of process.
• Enterprise customer-facing experience. You’re comfortable in a room with a CMO and equally comfortable debugging a failing build.
• A bias toward doing the work yourself, not delegating it. You want to build, not just manage.

Nice to Have

• Experience building or scaling a solutions engineering, professional services, or technical consulting practice.
• Familiarity with synthetic data, audience enrichment, or data clean rooms.
• Background in programmatic advertising, DMP/CDP platforms, or marketing analytics.
• You’ve defined the process and methodology for a team that didn’t exist before you joined.

How to Apply

Show us how you think about building with AI. A project you’ve shipped, a framework you’ve developed for your team, a writeup of your approach — anything that shows you’re already doing this work and thinking about how to make others better at it.

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.