Overview
An organization is seeking an experienced commercial or transactional lawyer to serve as a part-time domain expert for an AI-powered legal work surface designed for a large global investment organization. This product aims to assist in-house lawyers in managing legal work across matters, emails, documents, playbooks, prior transactions, external counsel outputs, and internal systems.
Responsibilities
- Guide product and engineering teams by explaining real legal workflows, including how legal requests arrive, matter organization, document review, escalation processes, and decision rationale preservation.
- Provide practical legal and product guidance on commercial agreements, matter workflows, risk assessment, negotiation strategy, and legal operations.
- Review and evaluate product concepts and workflows to ensure alignment with actual legal practices, identifying missing steps, edge cases, or unrealistic assumptions.
- Explain legal judgment behind contract clauses, including acceptance, rejection, redlining, context requirements, or escalation.
- Assess AI-generated outputs such as summaries, issue identification, clause classifications, redline recommendations, obligation extraction, and precedent retrieval for accuracy and legal reasoning.
- Develop evaluation rubrics and benchmarks defining high-quality outputs and create representative examples for AI training and testing.
- Generate high-quality ground-truth data by reviewing agreements, labeling legally relevant information, documenting supporting evidence, and providing concise written reasoning.
- Advise on modeling institutional legal knowledge, including playbooks, prior positions, counterparty history, precedent, approvals, and negotiation rationale.
- Provide direct, specific feedback on product accuracy, completeness, confidence levels, and trustworthiness from a lawyer's perspective.
- Occasionally support customer discovery by participating in working sessions or customer conversations to clarify requirements or validate workflows.
Requirements
- Must be based in the United States.
- 5+ years of legal experience preferred, with significant hands-on experience reviewing, drafting, and negotiating commercial or transactional agreements. Candidates with fewer years but relevant experience may be considered.
- Experience as an in-house lawyer, senior associate, legal consultant, or transactional counsel supporting complex organizations or sophisticated commercial clients.
- Strong familiarity with commercial agreements such as NDAs, services agreements, procurement/vendor agreements, technology agreements, licensing agreements, transaction documents, or other negotiated contracts.
- Ability to independently review agreements, identify material issues, evaluate practical risk, and explain reasoning behind recommended positions.
- Experience using playbooks, precedent, prior agreements, negotiation history, or organizational risk tolerance in advising contract positions.
- Strong written communication skills for producing structured explanations and written evaluations.
- Ability to clearly explain legal concepts to non-lawyers including engineers, product managers, and designers.
- Comfort working with incomplete information and distinguishing between conclusions supported by documents, those requiring additional context, matters for escalation, and those unsuitable for AI determination.
- Practical, opinionated perspective on what makes legal technology useful or unhelpful in real legal work.
- Qualification or admission as a lawyer in a U.S. jurisdiction.
Preferred Experience
Candidates with experience in one or more of the following areas may be especially well suited:
- In-house commercial legal work.
- Private equity, investment, M&A, funds, credit, real assets, or other transactional practices.
- Cross-border transactions or international commercial agreements.
- Working with investment organizations, financial institutions, sovereign entities, or complex multinational businesses.
- Managing external counsel or reviewing external counsel advice and issue lists.
- Developing contract playbooks, clause libraries, fallback positions, or approval frameworks.
- Legal operations, contract lifecycle management, matter management, or knowledge management.
- Post-signing obligations, closing checklists, amendments, consents, governance, or asset-management legal work.
Deep experience in every area is not required; strong commercial legal judgment and the ability to clearly explain that judgment are the primary focus.
Nice to Have
- Experience with legal AI, contract review software, CLM systems, knowledge-management tools, or AI-assisted drafting products.
- Prior collaboration with product, engineering, data science, or innovation teams.
- Experience creating legal training materials, review rubrics, model answers, or quality-control processes.
- Prior data annotation, evaluation, benchmarking, or expert-review work.
- Familiarity with tools such as iManage, DealCloud, Legora, Spellbook, Ironclad, or similar legal and transaction-management systems.
Ideal Candidate Attributes
- Enjoys explaining how experienced lawyers reach decisions, including judgment calls rarely captured in formal policies.
- Can translate complex legal reasoning into clear, structured guidance.
- Comfortable challenging assumptions and providing candid feedback.
- Able to distinguish between legally correct analysis and analysis useful in time-sensitive commercial workflows.
- Values provenance and can reference clauses, documents, playbook positions, precedent, or factual context supporting conclusions.
- Comfortable working with shared documents, asynchronous communication tools, and structured annotation or review interfaces.
- Interested in shaping AI tools that support lawyers without replacing lawyer-controlled judgment.
Confidentiality
This engagement involves exposure to sensitive commercial agreements and internal product information. A signed Non-Disclosure Agreement (NDA) will be required before work begins.
Compensation and Logistics
- Part-time contract engagement for U.S.-based candidates only.
- Approximately 5–10 hours per week.
- Initial engagement of 3–4 months with the possibility to extend.
- Flexible scheduling to accommodate existing legal roles or practices.
- Remote-friendly collaboration through shared documents, asynchronous communication, and recurring working sessions with product and engineering teams.
- Competitive hourly compensation commensurate with experience and expertise.
- NDA required prior to starting work.
Location