AI Attorney Associate Principal

The AI Attorney Associate Principal serves as a senior legal subject matter expert on the Firm's AI Engineering team, bringing deep legal-practice expertise to the development and adoption of AI-powered legal products. Reporting to the Senior Director of AI Engineering, this role partners with Product Design & UX, Engineering, Knowledge Management, and other stakeholders to translate lawyer workflows and quality expectations into product requirements, lead legal-quality evaluation, and help ensure AI products meet the Firm's standards for quality and professional responsibility. The AI Attorney Associate Principal also serves as a key advocate for the Firm's AI products, cultivating lawyer engagement and advising on developments in generative AI and legal technology.

Duties and Responsibilities:

• Serve as a senior legal subject matter expert for the AI Engineering team, applying practitioner insight into legal workflows, work product standards, and client expectations throughout product development.
• Shape product requirements and priorities in partnership with AI Engineering leadership and Product Design & UX, translating lawyer workflows, pain points, and quality expectations into requirements, user stories, acceptance criteria, and product improvements.
• Lead discovery with lawyers and practice groups to understand workflows and identify and prioritize high-value opportunities for AI-enabled legal work, including drafting, contract review and analysis, due diligence, research, summarization, and knowledge retrieval.
• Partner with Product Design & UX and Engineering to improve product experiences, applying a practitioner's perspective to interfaces, prompts, agentic workflows, and outputs to meet lawyers' expectations for accuracy, citation, format, tone, and usability.
• Lead legal-quality evaluation of AI products, developing evaluation rubrics, gold-standard datasets, and test cases; coordinating expert review of AI outputs; and identifying improvements to prompts, retrieval, grounding, and model configuration.
• Partner with Knowledge Management and practice groups to incorporate Firm expertise into AI products, including relevant precedents, playbooks, clause libraries, templates, and other legal content used to ground and evaluate AI solutions.
• Serve as a key advocate for the Firm's AI products, demonstrating use cases to lawyers and Firm leadership, cultivating champions and early adopters across practices and offices, incorporating user feedback into product priorities, and supporting pilots, training, and product adoption.
• Embed responsible AI considerations into product development, partnering with the Office of General Counsel, Risk, Information Security, and Privacy to translate professional responsibility obligations, client requirements, and applicable AI regulations into practical product guardrails and controls.
• Evaluate legal AI vendors, models, and emerging capabilities, contributing legal and product expertise to build-versus-buy decisions, vendor due diligence, and assessments of new technologies and market developments.
• Advance legal AI product practices and team capabilities by improving processes and standards for defining, evaluating, and launching legal AI products; communicating product direction, outcomes, risks, and tradeoffs to senior stakeholders; and providing guidance, coaching, and subject matter expertise to other professionals.

Education and/or Experience:

Required:

• Juris Doctor (J.D.) from an ABA-accredited law school and admission in good standing in at least one U.S. jurisdiction.
• A minimum of 8 years of legal experience, including substantive practice at a large law firm and/or in the legal department of a major financial institution, technology company, or other complex enterprise.
• A minimum of 2 years of experience focused on generative AI or legal technology, including advising on, designing, evaluating, or deploying AI-enabled solutions.
• Deep understanding of law firm workflows, legal work product, and lawyers' expectations for quality, precision, and risk management.
• Demonstrated experience working cross-functionally with product, engineering, and business stakeholders across the product development lifecycle.
• Hands-on proficiency with generative AI tools and demonstrated ability to evaluate AI output quality, limitations, and failure modes.
• Working knowledge of AI governance, professional responsibility, confidentiality, and data privacy considerations applicable to AI use in legal practice.
• Demonstrated ability to communicate complex legal, technical, and regulatory concepts to lawyers, executives, and non-technical audiences and influence senior stakeholders.
• Ability to lead complex, cross-functional initiatives with a high degree of independence, navigate ambiguity, balance competing priorities, and exercise sound judgment.

Preferred:

• Transactional legal practice experience, such as finance, capital markets, commercial and technology transactions, or mergers and acquisitions.
• Experience developing standardized legal templates, playbooks, clause libraries, or similar knowledge resources.
• Familiarity with large language model concepts and technologies, including retrieval-augmented generation (RAG), embeddings, agents, evaluation frameworks, and AI- or code-based prototyping tools.
• Experience with Agile product delivery practices and tools.
• Knowledge of applicable AI regulatory, governance, and legal ethics frameworks.
• Experience presenting or publishing on legal AI, legal technology, or related topics.
• Relevant AI governance or privacy certification.

Other Skills and Abilities:

The following will also be required of the successful candidate:

• Strong organizational skills.
• Strong attention to detail.
• Good judgment.
• Strong interpersonal communication skills.
• Ability to manage multiple projects with competing deadlines and priorities.
• Ability to work effectively under pressure.
• Strong analytical skills and a proactive approach to problem-solving.
• Able to work harmoniously and effectively with others.
• Able to preserve confidentiality and exercise discretion in all interactions.

The target salary range for this role is:

$202,000 - $287,000 if located in Illinois.

Salaries vary by location and are based on numerous factors, including, but not limited to, the relevant market, skills, experience, and education of the selected candidate. Our compensation package also includes bonus eligibility and a comprehensive benefits program. Benefits information can be found at Sidley.com/Benefits.

To perform this job successfully, an individual must be able to perform the Duties and Responsibilities above satisfactorily and meet the requirements. The requirements listed above are representative of the minimum knowledge, skill, and/or ability required. Reasonable accommodations will be made to enable individuals with disabilities to perform the essential functions of the job. If you need such an accommodation, please email sidleytalentacquisition@sidley.com (current employees should contact Human Resources).

Sidley Austin LLP is an Equal Opportunity Employer.

Sidley is an elite global law firm with a known reputation of deploying innovative strategies to achieve powerful results.

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Business professionals are essential to the firm’s ability to deliver the highest quality legal services to our clients. We are always looking for talented, motivated individuals who thrive in a performance-driven culture to join our team.

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More About Sidley

Sidley employs approximately 2,300 lawyers working with our clients in complex transactional, restructuring, crisis management, investigation, regulatory, and litigation matters.

Our 160 years of perspective and reach are truly global, supported by 21 offices strategically situated in key commercial, regulatory, and financial centers across the world. Our lawyers and business professionals, fluent in more than 75 languages, possess the cultural awareness and cross-border legal acumen needed to bring clarity to a dynamic business landscape.