Deployment Strategist - New York

About Draftwise

Draftwise is a contract drafting, review, and negotiation AI powered by your legal knowledge. We turn a firm's guidance, precedent, and language into a legal ontology, ground our models in it, and run complex drafting, review, and search workflows directly within Microsoft Word and in the browser.

We serve top law firms and legal departments globally, including over half the Vault 10, dozens of Am Law 100 firms, and Fortune 500 organizations. We are headquartered in NYC with offices in London and West Palm Beach, are Y Combinator alumni, and raised a $20M Series A from Index Ventures.

About this role

We are looking for a Deployment Strategist to embed with leading law firms, discover where Draftwise can create transformational value, and turn that discovery into outcomes for customers and repeatable product capabilities.

This is a forward-deployed role. The center of gravity is product discovery in the field: learning how lawyers actually work, identifying the highest-value problems, and understanding the documents, data, systems, and organizational constraints behind them. You will be accountable for driving transformational outcomes for the customer. Those outcomes must be demonstrable and measurable.

You will move comfortably between conversations with managing partners and C-level executives, working sessions with associates and knowledge teams, and technical discussions with customer IT and Draftwise engineers. You will distill what you learn into clear product requirements, scope them with Product, Engineering, and ML, track them through delivery, and validate the result with users.

Every engagement should create leverage beyond a single customer. You will distinguish one-off requests from recurring needs and help turn validated patterns into reusable product capabilities, evaluations, configurations, and playbooks.

What you'll do

• Embed with customers, often onsite, to observe how partners, associates, knowledge professionals, innovation teams, and IT teams work, and uncover high-value problems they may not yet be able to articulate.

• Define the customer outcome before prescribing a solution, then map the workflows, decisions, documents, data, systems, organizational constraints, and incentives that shape where and how Draftwise can create the greatest value.

• Work directly with customer documents, data, systems, and Draftwise tools to test feasibility and determine where AI can create transformational value.

• Distill user and customer needs into clear product requirements; scope them with Product, Engineering, and ML; make trade-offs; track the work; and drive it through delivery.

• Build and configure prototypes, demos, data transformations, lightweight automations, and evaluations; put them in front of real users early and iterate from evidence.

• Identify which needs are customer-specific and which reveal repeatable patterns; help turn validated patterns into reusable platform capabilities, configurations, evaluations, and playbooks.

• Present findings, requirements, trade-offs, and outcomes credibly to managing partners, customer IT, frontline users, and Draftwise teams, using field evidence to shape what we build next.

What you'll bring

• 3+ years of experience in deployment strategy, forward-deployed work, product discovery, solutions engineering or consulting, or another customer-facing technical role where you owned outcomes in complex environments.

• A track record of taking ambiguous, high-stakes customer problems from discovery, to clear product requirements, to shipped solutions that produced material customer outcomes.

• Strong analytical judgment and the instinct to get beneath stated requirements and understand the workflow, the data, the organizational dynamics, the real constraints, and where value is ultimately created.

• Strong technical fluency and hands-on experience with modern AI tools. You can query data, work with APIs and data models, stand up a prototype or automation, use AI coding tools as a force multiplier, and critically evaluate their outputs and limitations.

• Exceptional written, verbal, and presentation skills, with the range to work credibly with executives, lawyers, technical teams, and frontline users.

• The delivery discipline to scope ambiguous work, make trade-offs, manage dependencies, track progress, and keep a cross-functional team oriented around the customer outcome.

• High ownership, low ego, sound judgment, and willingness to travel and spend meaningful time onsite with customers.

Helpful, but not required

• Familiarity with legal workflows, law-firm knowledge systems, document management systems, or other complex professional-services environments.

• Experience practicing law or working in legal innovation, knowledge management, legal operations, or legal technology.

What we value

• Clear communication and thoughtful, direct feedback.

• Autonomy, ownership, and consistently high-quality execution.

• Curiosity about how people, data, and systems work in the real world.

• Comfort with changing objectives and imperfect information.

• A collaborative approach that builds trust across customers and internal teams.

What we offer

• Meaningful equity, giving you a stake in Draftwise's growth.

• Competitive salary.

• Private medical care.

• A work-from-home stipend for necessary equipment and accessories.

• Unlimited PTO and sick leave.

• The opportunity to shape how a fast-growing company deploys AI in the legal industry.