AI Attorney Associate Principal

Sidley Austin•Chicago, IL

1d•$202,000 - $287,000•Hybrid

About The Position

The AI Attorney Associate Principal serves as a senior legal subject matter expert on the Firm's AI Engineering team, bringing legal-practice expertise to the development and adoption of AI-powered legal products. Reporting to the Senior Director of AI Engineering, the 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 quality and professional responsibility standards. The role also advocates for the Firm's AI products, cultivates lawyer engagement, and advises on developments in generative AI and legal technology. The position leads discovery with lawyers and practice groups; shapes product priorities and experiences; develops evaluation rubrics, datasets, and test cases; and incorporates Firm expertise into AI products. It supports product adoption through demonstrations, pilots, training, and feedback, and embeds responsible AI considerations in partnership with legal, risk, security, and privacy stakeholders. The role also evaluates vendors and emerging technologies, advances product practices, communicates with senior stakeholders, and provides guidance and coaching to other professionals.

Requirements

Juris Doctor (J.D.) from an ABA-accredited law school and admission in good standing in at least one U.S. jurisdiction.
At least 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.
At least 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.
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 independently, navigate ambiguity, balance competing priorities, and exercise sound judgment.
Strong organizational skills and attention to detail.
Good judgment and strong interpersonal communication skills.
Ability to manage multiple projects with competing deadlines and priorities and work effectively under pressure.
Strong analytical skills and a proactive approach to problem-solving.
Ability to work harmoniously and effectively with others.
Ability to preserve confidentiality and exercise discretion in all interactions.

Nice To Haves

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.

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 with AI Engineering leadership and Product Design & UX, translating lawyer workflows, pain points, and quality expectations into requirements, user stories, acceptance criteria, and improvements.
Lead discovery with lawyers and practice groups to understand workflows and identify and prioritize 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, including interfaces, prompts, agentic workflows, and outputs, to meet lawyers' expectations for accuracy, citation, format, tone, and usability.
Lead legal-quality evaluation of AI products by 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, including precedents, playbooks, clause libraries, templates, and other legal content, into AI products.
Advocate for the Firm's AI products by demonstrating use cases, cultivating champions and early adopters, incorporating user feedback into product priorities, and supporting pilots, training, and 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 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 technology and market assessments.
Advance legal AI product practices and team capabilities by improving processes and standards for defining, evaluating, and launching products; communicating direction, outcomes, risks, and tradeoffs to senior stakeholders; and providing guidance, coaching, and subject matter expertise.