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 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

you're

building with today's tools, not describing

yesterday's.

You're

technical-adjacent

and unafraid of it.

You

don't

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.

You're

relentlessly practical.

You care about what works in production and what changes client behavior, not what sounds impressive in a deck.

You're

comfortable with ambiguity.

Harbor Labs is

new

and the market is evolving.

You'll

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

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