[Hiring] Head of Forward Deployed Engineering & Deployment Strategy @Breakmark

Role Description

As Head of FDE & DS, you’ll lead the team that deploys the company’s AI agents inside customers’ operations. The team has two tracks: Forward Deployed Engineers (FDEs), who take on technically complex implementations, and Deployment Strategists (DS), who lead less complex, commercially driven ones. Your mission is to make every deployment technically excellent, repeatable and faster than the last.

You’ll own implementation end to end:

• Which process each deployment targets
• Stakeholder alignment
• The technical bar
• Team assignments and capacity
• Hiring
• The loop that turns field work into product

This is not a project management role. It’s a hands-on technical leadership position reporting to the COO.

Qualifications

• Experience leading forward deployed, solutions or implementation engineering teams in B2B software
• Deep AI and engineering expertise: you’ve shipped LLM or agent systems to production, not just demos
• Hands-on experience with enterprise integrations (ERP, WMS, TMS or similar), working directly with customers’ IT and data teams
• Operational judgment to pick the right processes to automate and align executives and operators around them
• Track record of hiring and coaching customer-facing technical talent
• Curiosity about how supply chain and logistics operations really work (industry experience is a plus, not a requirement)
• Bias to ship, comfort with ambiguity, and a strong ownership mindset with cross-functional collaboration skills

Requirements

• Lead, coach and grow a team of FDEs and Deployment Strategists
• Hire production-grade engineers who work directly with customers, and strategists with strong AI literacy and commercial judgment
• Ramp new hires quickly and keep the team stable
• Review the Statement of Work, client brief and stakeholder map with the Account Executive and deployment owner
• Keep deployments focused on processes that convert, avoiding fragmentation into custom work
• Resolve stakeholder friction and act as the escalation point when a deployment stalls
• Assign one owner (FDE or DS) to every deployment before kickoff, based on technical complexity
• Pair in an FDE or hand over when a strategist-led deployment becomes technically complex
• Protect capacity by ensuring clean handoffs to Customer Success
• Set the technical approach for each 90-day Proof of Concept and its 7-day value sprint
• Unblock hard build problems, from agent design to data and workflow wiring
• Hold the quality bar on discovery, build and testing so agents run on real customer data before the value demo
• Own the expansion scope and business case alongside the Account Executive
• Own the integration plan for client systems
• Hold the go/no-go on data readiness: no build starts until connectivity, credentials and data quality are confirmed
• Run a weekly review of field work so every sprint produces at least one reusable asset
• Partner with Engineering to turn field workarounds into product
• Bring structured, actionable feedback from deployments to Product
• Own team health metrics: time to value, agent outputs, efficiency per deployment owner, reusable assets, expansion workflows per customer, ramp and retention
• Use those metrics to decide where to coach, hire and standardize

Company Description

The company is a fast-growing AI startup that turns fragmented operational and document-based data into a single source of truth, enabling AI agents to run end-to-end workflows for B2B companies. They operate in complex, real-world domains (starting with supply chain and logistics) where systems need to be reliable, scalable and deeply integrated with external partners.