Director of AI Engagements

Role Description

We're 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.
• You'll 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 client's 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 focus on hard, novel problems where standard platforms fall short.
• The work is ambiguous, the solutions aren't obvious, and that's the point.

What You'll Do:

• Own the strategy for your engagements. Shape what success looks like with the client's leadership, define the roadmap, and make the prioritization calls.
• Lead at the executive level. Be the trusted partner to GCs, COOs, and heads of legal operations.
• Stay hands-on with the work. Configure systems, structure knowledge sources, write and refine prompts, design test cases, and validate outputs against real data.
• Set direction for delivery. Define how an engagement is scoped, staffed, and sequenced.
• Design the operating model, not just the workflow. Figure out how AI changes the way a legal team operates.
• Drive architecture and integration decisions. Partner with engineers on how AI fits into client tech stacks.
• Help build Harbor Labs itself. This is a ground-floor leadership opportunity.

Qualifications

• You operate like an owner. You've run engagements, programs, or a function end-to-end and been accountable for the result.
• You lead from the front, hands on the work.
• You've delivered real change in how teams work.
• You're deeply fluent in AI, but not captured by hype.
• You hold current model-provider credentials.
• You're technical-adjacent and unafraid of it.
• You command a room at any level.
• You're relentlessly practical.
• You're comfortable with ambiguity.

Requirements

• 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.

Benefits

• We're a small, senior team working on hard problems with clients who are serious about deploying AI in production.
• The work is hands-on, the ownership is real, and the leadership you exercise here will directly shape what this team becomes.
• This is early. You'll have meaningful input into the strategy, the team, and what Harbor Labs grows into.

How to Apply

Send us a note about why this role interests you and an engagement or initiative you led that you're 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.