Director, Forward Deployed Engineering

About Chalk

Chalk (chalk.ai) is the platform for production AI. Trusted by enterprises including Whatnot, Grindr, Mission Lane, Turo, and Apartment List, Chalk brings together context, runtime, and learning for agents and models. Chalk’s Context Engine delivers live context by querying data across warehouses, databases, streams, and APIs, straight from the source. Chalk’s runtime powers agents and models with infrastructure and governed access to LLMs and tools. Together, these capabilities help teams build AI that understands their business, continuously improves, and runs reliably in production. We've recently raised a $50 million Series A, led by Felicis. Learn more at chalk.ai.

About the role

Forward Deployed Engineering is where Chalk meets its customers. Our FDEs are exceptional software engineers who integrate Chalk’s platform with the best ML and engineering teams in healthcare, finance, and consumer technology — running technical pilots that win deals, onboarding new customers, and engineering feature pipelines that power use cases like fraud prevention, cancer detection, and product recommendation.

Working directly with our founders, you'll lead this team and define its future. You'll own the strategy for how Chalk engages customers technically — from pre-sales pilots through onboarding, support, and expansion — and build the organization, processes, and playbooks that let the function scale with our growth. FDE is one of the most strategically important and fastest-growing functions at Chalk, and this role will shape what it becomes.

We're in the office 5 days a week. When unavoidable conflicts come up, we’re flexible. This is not a hybrid role.

What you will do

• Lead, develop, and retain Chalk's team of Forward Deployed Engineers across New York and San Francisco, and own an aggressive hiring plan as the team scales
• Define the strategy and operating model for the FDE function: engagement models, account coverage, the pre-sales/post-sales balance, and how FDEs drive expansion within accounts
• Own the systems that make the team run — support triage and rotations, escalation paths to Engineering, onboarding playbooks, and the processes for rolling out platform changes to customer environments
• Partner closely with Sales and GTM leadership on technical pilots, evaluations, and the technical strategy behind our most important deals
• Partner with Engineering leadership to channel customer learnings into the product roadmap and to sharpen the internal tooling FDEs rely on
• Stay hands-on: dive into customer architectures, unblock hard technical problems, and set the technical bar for the team
• Serve as an executive-level technical counterpart to customer leadership at our largest accounts
• Define career paths and growth trajectories for FDEs, and champion the function's identity as we grow — deeply technical engineers embedded with customers, not sales engineering

What we're looking for

• 10+ years of engineering experience with 3+ years leading customer-facing engineering teams (forward deployed, solutions architecture, field engineering, or similar)
• Strong hands-on technical skills — proficient in Python and SQL, comfortable going deep on customer architectures and data infrastructure
• Experience across both pre-sales and post-sales complex enterprise motions: technical pilots and evaluations as well as onboarding, support, and account expansion
• Proven ability to hire, develop, and retain exceptional engineers, including senior ICs
• Previous experience at an early-stage, high-growth startup
• Executive-level communicator who can bridge technical, business, and customer contexts
• Experience building the processes and playbooks that let a customer-facing engineering team scale
• Bachelor's degree in Computer Science or equivalent

Bonus points

• Previous experience as a forward deployed engineer or FDE leader at a high-growth startup
• Experience building production ML systems, ML infrastructure, or data platforms
• Experience scaling a customer-facing engineering function from single-digit to multi-team
• Experience working with enterprise customers in regulated industries (fintech, healthcare)