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Deployment Strategist - New York

Draftwise· Operations
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Hybrid (New York City, NY)$150k - $190kFull-timePosted 1mo ago

About the role

Deployment Strategist to embed with leading law firms, identify high-value problems, and translate discovery into measurable customer outcomes and reusable product capabilities.

Responsibilities

  • 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.

Qualifications

  • 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.

Skills

Required:Deployment strategyProduct discovery and requirementsAI tools & prototypingStakeholder communication

Benefits

  • 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.
Last updated Sep 23, 2026. Interested? Apply on the company site.
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About Draftwise

Contract and negotiation AI built for lawyers

Draftwise is redefining contract work for lawyers with AI that streamlines drafting, review, and negotiation. Draftwise empowers lawyers with intelligent, data-driven tools that use a firm’s own knowledge base—drawing from past deals, preferred language, and internal guidance to improve the entire contract workflow—from first draft to signed deal.

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