We9re looking for a
Director of AI Engagements to lead our most important client relationships and set the strategy for how we deploy AI in production. This is a senior role for someone who can sit across the table from a GC or COO, shape the direction of an engagement, and then roll up their sleeves and build alongside the team to deliver it.
This is a leadership role, but not a hands-off one. You9ll own the strategy for your engagements and stay close enough to the work to configure systems, pressure-test outputs, and make the calls that determine whether AI actually sticks in a client9s day-to-day.
What Makes This Different: Our edge is combining deep legal domain experience with product sensibility and strong engineering. We understand how legal teams actually work, what change management looks like in risk-averse environments, and how to build software that people will use. We also know the common pitfalls of enterprise software in traditionally low-innovation areas like law, and we9re determined to avoid them.
We focus on hard, novel problems where standard platforms fall short. The work is ambiguous, the solutions aren9t obvious, and that9s the point. As a senior leader here, you set the bar for how we approach those problems and how we show up with clients.
What You9ll Do:- Own the strategy for your engagements. Shape what success looks like with the client9s leadership, define the roadmap, and make the prioritization calls. You9re accountable for the outcome and the relationship, not just the deliverable.
- Lead at the executive level. Be the trusted partner to GCs, COOs, and heads of legal operations. Translate where AI is heading into a concrete plan they can get behind, and bring skeptics along.
- Stay hands-on with the work. Configure systems, structure knowledge sources, write and refine prompts, design test cases, and validate outputs against real data. You lead from inside the work, not above it.
- Set direction for delivery. Define how an engagement is scoped, staffed, and sequenced. Work shoulder-to-shoulder with engineers and delivery leads to turn an ambiguous business problem into a production system.
- Design the operating model, not just the workflow. Figure out how AI changes the way a legal team operates: the processes, the roles, the governance. Redesign how the work gets done, then make the change actually happen.
- Drive architecture and integration decisions. Partner with engineers on how AI fits into client tech stacks: APIs, data flows, security and compliance requirements. Hold the line on what9s production-grade.
- Help build Harbor Labs itself. This is a ground-floor leadership opportunity. You9ll shape how we sell, how we deliver, who we hire, and where we go next.
What We9re Looking For:- You operate like an owner. You9ve run engagements, programs, or a function end-to-end and been accountable for the result. You set direction when there isn9t one and you don9t wait for permission to fix what9s broken.
- You lead from the front, hands on the work. Seniority hasn9t pulled you away from the details. You9re as comfortable in a configuration screen or a prompt as you are in a boardroom, and you believe the two can9t be separated.
- You9ve delivered real change in how teams work. You understand legal operations, professional services, or a comparable environment, and you9ve redesigned how people actually do their jobs, not just shipped a tool.
- You9re deeply fluent in AI, but not captured by hype. You understand how these systems work in production: RAG architectures, agentic workflows, prompt engineering, evaluation methods. You know how to separate signal from noise when every vendor claims to be the next breakthrough.
- You hold current model-provider credentials. Anthropic Academy certifications (AI Fluency: Framework & Foundations, Claude Code, Building with the Claude API, Model Context Protocol) are a strong plus, and current OpenAI Academy coursework counts too. We treat these as a real signal, not a checkbox: they show you9re building with today9s tools, not describing yesterday9s.
- You9re technical-adjacent and unafraid of it. You don9t need to write Python all day, but you can read an API doc, reason about a system architecture, and have a credible conversation with engineers about tradeoffs.
- You command a room at any level. Executive presentations, working sessions with skeptical users, hard conversations about scope and risk. You build trust fast and hold it under pressure.
- You9re relentlessly practical. You care about what works in production and what changes client behavior, not what sounds impressive in a deck.
- You9re comfortable with ambiguity. Harbor Labs is new and the market is evolving. You9ll set the playbook, not follow one.
Nice to Have:- Senior experience in legal operations, legal technology, or a transformation/innovation function
- Track record leading client engagements in consulting or professional services
- Experience at a product company (product, solutions, or delivery leadership)
- Hands-on experience with a broad range of AI development tools and LLM APIs
How to Apply: Send us a note about why this role interests you and an engagement or initiative you led that you9re proud of, ideally one where you set the strategy and stayed close to the work. Examples and references matter more to us than a polished resume.
