Product Manager

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 seeking a Product Manager to own product areas end to end while working closely with our customers.

You will discover where Draftwise can create transformational value, translate customer and user needs into clear product requirements, and drive scoped work through launch and measurable outcomes. We pride ourselves on a product approach built around close iteration with the people who use what we build. You will spend significant time with customers, working in their documents and their systems, running sessions with their teams, and putting rough versions in front of real users while there is still time to change them.

The hardest problems we solve may start with one customer. Your job is to distinguish one-off requests from recurring needs, make the case for what belongs in the platform, and ensure each solution creates leverage beyond the initial customer. You will move comfortably between individual users, cross-functional product teams, managing partners, C-level executives, and heads of innovation.

Key Responsibilities

• Discover the highest-value customer problems

  • Spend meaningful time with law firm partners, associates, knowledge teams, practice technology leads, and customer IT to understand how work actually happens, not just how it is described.

  • 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 and data, and build prototypes, demos, transformations, and evaluations to test assumptions with real users before committing to a direction.

  • Apply strong AI product judgment: know when AI is the right tool, understand relevant model capabilities and failure modes, and define the evaluations and human controls required for a trustworthy product.

• Turn discovery into shipped product and customer outcomes

  • Distill customer and user needs into clear product requirements, scope them with Engineering, ML, and Design, and own the prioritization and trade-off decisions.

  • Own one or more product areas from problem definition and roadmap development through delivery, launch, and measurable customer outcomes.

  • Help incorporate Draftwise's new legal ontology offering into the core product, defining how it strengthens existing workflows and creates new customer value as part of a coherent product experience.

  • Define success measures up front, track progress through delivery, and stay accountable when results fall short.

  • Align Engineering, ML, Design, Customer Success, Marketing, and Sales around the product direction and what is required to make it successful.

  • Partner closely with Sales, Customer Success, and Implementation to understand what drives adoption, expansion, and retention, and incorporate those signals into product strategy and prioritization.

  • Build for the realities of enterprise software, including security, permissions, integrations, governance, administration, and multi-stakeholder rollout, while maintaining a coherent and scalable product.

• Create leverage across customers

  • Distinguish customer-specific requests from recurring needs and make the evidence-based case for what belongs in the core platform.

  • Work with Engineering to turn validated patterns into reusable product capabilities, configurations, evaluations, and playbooks.

  • Use field evidence across customers to shape forward-looking product strategy, and communicate decisions, trade-offs, and outcomes clearly to users, executives, and internal teams.

About you

We're looking for teammates who possess:

• 6+ years in product management, forward-deployed engineering, deployment strategy, or a comparable customer-facing technical role, including experience building enterprise software for complex, multi-stakeholder organizations. You have taken ambiguous problems from discovery to shipped solutions and material customer outcomes, owned those outcomes beyond launch, and can support them with adoption data, business metrics, or clear user evidence.

• Strong analytical judgment and the instinct to get beneath surface-level requirements, understand the workflow and organizational context, interrogate the underlying data, and turn open-ended problems into something buildable.

• Strong technical fluency and AI product judgment. You can stand up a working prototype, query a dataset, work with APIs and data models, or automate your own workflow without waiting on an engineer. You understand the capabilities and limitations of modern AI systems, know when AI is the right tool, define appropriate evaluations and human controls, make principled trade-offs among quality, latency, cost, and trust, and critically evaluate outputs when something looks wrong.

• Strong product judgment and communication. You form evidence-based opinions, make clear prioritization and trade-off decisions, explain why a product or design choice fits its users and constraints, align cross-functional teams, and engage credibly with senior customer stakeholders.

• High ownership, low ego, and comfort working independently in an unstructured environment, with a preference for being close to users over managing process or people.

• Willingness to travel and work onsite with customers regularly.

• Interest in legal technology. Experience practicing law is helpful but not required.

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.