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Riverside, California, United States
Remote only
Head of Forward Deployed Engineering & Deployment Strategy | AI Startup
đź“Ť Remote / On-site travel
About the company
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.
The role
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, and 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.
What you’ll do
Team leadership & hiring
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
Scoping & stakeholder alignment
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
Assignment & capacity
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
Technical excellence
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
Expansion & integrations
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
Field-to-product loop
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
Team performance
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
What they’re looking for
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
