AI Deployment Strategist

Join us in building the autopilot for legal services

Today, legal work is done the way it has been done for a century — manually, by humans, in six-minute increments. Every contract drafted from scratch. Every memo researched line by line. Every matter running through layers of review that someone is paying for at hundreds of dollars an hour.

That is about to change. We believe that in five years, more than 80% of legal work will pass through a model before it ever reaches a human. The implication is not faster lawyers — it is a fundamentally different way that legal services get bought and procured.

Our mission is to make high-quality legal work accessible and affordable for everyone. We are going after the services spend, not the software spend — helping law firms restructure their delivery model around AI, and helping in-house teams do the same. One engine of agents and workflows underneath every matter we touch.

We are a lean, in-person based in New York City, backed by leading investors and growing fast. Every role at August is a chance to remake an industry while the window is open.

About the Role

As an AI Deployment Strategist, you will be the person who walks into a law firm and actually changes how it operates. You will embed with clients, earn trust at every level of the organization, identify where AI can replace manual workflows, and own the transformation from discovery through full adoption. This is not a coordination role — you are in the field, running sessions, building solutions, and making things happen.

What you’ll do

• Embed with client organizations and run structured AI discovery across teams and practice groups — mapping workflows, uncovering pain points, and identifying where time is being wasted.

• Conduct one-on-one sessions with lawyers, paralegals, and legal ops staff to find out what they wish AI could do for them — going deeper than demos to surface the real opportunities.

• Run generalist AI training sessions across user groups, showing people what’s possible and helping them rethink how their work gets done.

• Map and automate legal workflows — document review, form filling, intake, drafting, redlining, matter management — and build lightweight proofs-of-concept to demonstrate value quickly.

• Own the go-live for AI solutions within client organizations from kickoff through full adoption, coordinating technical resources on both sides.

• Serve as the primary point of contact for client stakeholders throughout the engagement, running structured check-ins and business reviews.

• Translate what you learn in the field directly into product feedback for August’s engineering team.

What we’re looking for

• Strong product sense — you understand what makes a workflow painful and what would actually fix it, even without deep engineering knowledge.

• Business acumen and interpersonal range — you can earn trust with a managing partner and a legal ops analyst in the same afternoon.

• Natural curiosity — you go deep in conversations, ask unexpected questions, and find the real problem underneath the stated one.

• Comfort with ambiguity — there is no playbook here; you will be helping write it.

• 1–3 years of experience in consulting, legal ops, client success, product, or a client-facing role at a tech company. Background in law or legal services is a plus.

• Familiarity with workflow automation or no-code tools (Zapier, Make, n8n, or similar) is helpful but not required.

• Excitement about working in person at our NYC office with a team that values precision, pace, and constant reinvention.

Benefits

• Medical insurance coverage

• Flexible PTO

• Parental Leave

• Centralized office equipment ordering for all employees

• Equinox or Chelsea Piers gym membership

• In-office perks: lunch, dinner, snacks, drinks, and more

• Budget for intra-office travel

• Team-building events

• Relocation support to NYC (as needed)

Why Join August

• Founding Impact: Shape not just your role but the company.

• Uncapped Upside: Competitive base + commission, early equity ownership.

• Top-tier Team: Work alongside people who move fast, think clearly, and care deeply.

• Category-Defining Work: Help build the first true AI agents for the legal profession.

• Fast Growth: Scale your career as we scale the company.

• In-person in NYC: Collaborative, talent dense and high energy environment

• Global Reach: Our clients span 4 continents and use August in multiple languages and jurisdictions

• Frontier of Applied AI: August has access to proprietary data inaccessible to foundation model providers. We build agents to automate all challenging knowledge work.