Director, AI Engagements

Harbor Labs is a new team within Harbor focused on solving hard AI implementation problems in the legal market. We have strong hypotheses about what works, but we're building this like a startup: learning as we go, adjusting direction based on what the market tells us, and staying flexible about how we operate. 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 also know the common pitfalls of enterprise software in traditionally low-innovation areas like law, and we're determined to avoid them. 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. As a senior leader here, you set the bar for how we approach those problems and how we show up with clients. 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. You're 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 what's production-grade. Help build Harbor Labs itself. This is a ground-floor leadership opportunity. You'll shape how we sell, how we deliver, who we hire, and where we go next. What We're Looking For: You operate like an owner. You've run engagements, programs, or a function end-to-end and been accountable for the result. You set direction when there isn't one and you don't wait for permission to fix what's broken. You lead from the front, hands on the work. Seniority hasn't pulled you away from the details. You're as comfortable in a configuration screen or a prompt as you are in a boardroom, and you believe the two can't be separated. You've delivered real change in how teams work. You understand legal operations, professional services, or a comparable environment, and you've redesigned how people actually do their jobs, not just shipped a tool. You're 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…