Director of Forward Deployed Engineering

Chalk; New York (NY); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Health insurance

401(k)

Paid time off

Lunch provided

Commuter benefits

Job summary

Chalk seeks a senior leader to head Forward Deployed Engineering in New York and San Francisco, owning the strategy for customer engagement—from pilots to onboarding and expansion—and building a scalable organization.

You will hire, mentor, and define career paths for FDEs, drive pilots through onboarding and expansion, and ensure rigorous technical standards across customer engagements.

Qualifications

• 10+ years of engineering experience with 3+ years leading customer-facing teams.
• Bachelor's degree in Computer Science or equivalent.
• Proven ability to hire, develop, and retain engineers.
• Experience building production ML systems or data platforms.
• Executive-level communicator bridging tech, business, and customers.

Responsibilities

• Lead and scale a team of Forward Deployed Engineers across NY and SF.
• Own the FDE strategy, engagement models, and account coverage.
• Partner with Sales, GTM, and Engineering to drive pilots, evaluations, and product roadmaps.
• Define career paths and champion the FDE identity.
• Manage onboarding playbooks, escalation paths, and platform rollouts.

Skills

Python

SQL

Leadership

Customer-facing

Strategic thinking

Education

Bachelor's degree in Computer Science or equivalent

Tools

ML Systems

Data Pipelines

Job description

• 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
• 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

Benefits

• Full medical, dental, and vision insurance
• Flexible Spending Account (FSA) and Health Savings Account (HSA)
• Expert healthcare guidance and live one-on-one support
• 401(k) retirement savings
• Generous holiday schedule
• Generous PTO annually
• Daily lunch and dinner on us
• Flex commuter benefits
• Grab a ride home on us

Experience across both pre-sales and post-sales complex enterprise motions: technical pilots and evaluations as well as onboarding, support, and account expansionProven ability to hire, develop, and retain exceptional engineers, including senior ICsExperience building the processes and playbooks that let a customer-facing engineering team scaleStrong hands-on technical skills - proficient in Python and SQL, comfortable going deep on customer architectures and data infrastructureBachelor's degree in Computer Science or equivalentExecutive-level communicator who can bridge technical, business, and customer contextsPrevious experience at an early-stage, high-growth startup10+ years of engineering experience with 3+ years leading customer-facing engineering teams (forward deployed, solutions architecture, field engineering, or similar)Experience building production ML systems, ML infrastructure, or data platformsPrevious experience as a forward deployed engineer or FDE leader at a high-growth startupExperience scaling a customer-facing engineering function from single-digit to multi-teamExperience working with enterprise customers in regulated industries (fintech, healthcare)