Technical Deployment Lead – Forward Deployed Engineering

Jobtailor; Dublin; On-site; EUR 120,000 - 180,000; Full time

Job summary

Jobtailor is seeking a Senior Technical Delivery Leader to own the delivery plan for multiple AI-enabled customer engagements. Translate business objectives into roadmaps with milestones, dependencies, and acceptance criteria, and run day-to-day engineering execution across OpenAI FDE and client teams.

You will embed with customers to land production deployments, drive adoption, map workflows, and ensure fast, aligned decision making.

Qualifications

• 7+ years of customer-facing technical delivery leadership.
• Track record of leading large, complex customer engagements with AI at scale.
• Excel in high ambiguity environments and simplify complex problems.
• Able to map customer workflows, architectures, constraints and shipables.
• Recognise broader trends and translate needs into reusable solutions.
• Strong technical fluency and ability to discuss architectures and trade-offs.
• Experience shipping AI/LLM systems and production pitfalls awareness.
• Translator with executive presence who communicates complex trade-offs clearly.
• Onsite with customers to accelerate delivery (25-50%).
• Expertise in at least one major sector (healthcare, energy, financial services, semiconductors, IT).

Responsibilities

• Own the technical delivery plan for multiple interdependent workstreams with milestones and acceptance criteria.
• Run day-to-day engineering execution and coordinate across OpenAI FDE and customer teams.
• Embed with customer teams to land deployments and drive adoption through onboarding and change management.
• Partner with Product and Research to land platform components in time for deployment goals.
• Codify patterns and evals; extract reusable signals to improve products and models.
• Own value cases and ROI; set KPIs and report progress to exec sponsors.

Skills

Technical Delivery Leadership

AI/LLM Systems Experience

Customer Engagement Management

Strategic Thinking

Pattern-Matching

Change Management

Executive Presence

Job description

Responsibilities

• Own the technical delivery plan for multiple interdependent workstreams. Translate business objectives into a roadmap with milestones, dependencies, and acceptance criteria.
• Run day‑to‑day engineering execution. Track and drive delivery across OpenAI FDE and customer teams. Keep progress unblocked and sequenced. Make real‑time trade‑offs on scope and priority to protect the critical path.
• Embed with customer teams to land production deployments and drive adoption. Map workflows, shape tools/integrations, and translate requirements into a delivery plan. Lead onboarding, adoption, and change management.
• Partner with Product and Research so platform components and research workstreams land in time to support deployment goals.
• Codify solution patterns and evals. Extract reusable patterns and package field signals to improve product and models.
• Own value cases and ROI. Set impact hypotheses, baselines, and KPIs; run pre‑/post‑deployment measurement and report to exec sponsors.

Requirements

• 7+ years of customer‑facing technical delivery leadership.
• Track record of successfully leading large, complex, high‑stakes customer engagements where customer outcomes depended on tight coordination and fast decision making, ideally involving AI.
• Excel in high ambiguity environments. Know how to simplify complex and dynamic work.
• Move fluidly between system‑level understanding and execution‑level detail; can dive into customer workflows/data, map constraints, sketch architectures and move ambiguous problems to shipped systems.
• Think strategically and pattern‑match. Able to step back from execution detail, recognize broader trends across deployments, and connect customer needs to scalable, reusable solutions.
• Have strong technical fluency and sharp sequencing instincts. Confident discussing technical details, pressure‑testing architectures, and making trade‑offs.
• Have shipped AI/LLM systems. You understand solution patterns, integration basics, and production pitfalls.
• You’re a translator with executive presence. You make complex technical trade‑offs legible to business leaders and convert strategy into day‑to‑day technical execution.
• Enjoy being onsite with customers to accelerate delivery (often 25‑50%, sometimes higher).
• Have expertise in at least one major sector (e.g., healthcare, energy, financial services, semiconductors, IT) to elevate solution framing and credibility.

Core Competencies

Demonstrates expertise in technical delivery leadership, particularly in customer‑facing roles, with a strong focus on AI/LLM systems. Capable of translating complex technical requirements into actionable plans while ensuring alignment with business objectives and customer needs.

Highest‑signal resume keywords

• Technical Delivery Leadership
• AI/LLM Systems Experience
• Customer Engagement Management
• Strategic Thinking and Pattern‑Matching
• Change Management and Adoption

ATS Optimization Keywords

Hard Skills

• Technical Fluency
• Solution Patterns
• Integration Basics
• KPI Development
• Workflow MappingArchitecture Sketching
• Execution‑Level Detail
• Trade‑Off Analysis
• Pre/Post‑Deployment Measurement
• Customer Workflow Analysis

Soft Skills

• Executive Presence
• Simplifying Complex Problems
• Fast Decision Making
• Adaptability in Ambiguity
• Communication Skills

Industry Keywords

• Healthcare
• Energy
• Financial Services
• Semiconductors
• IT