AI Attorney Associate Principal

IL LLP; Chicago (IL); Hybrid; USD 202,000 - 287,000; Full time

Benefits offered by this job

Bonus eligibility

Benefits program

Job summary

Sidley Austin LLP seeks a senior AI attorney Associate Principal to lead legal-quality for AI engineering products. You will shape requirements with engineering and design teams, guide discovery with practice groups, and ensure outputs meet professional and regulatory standards.

With 8+ years of experience and a JD, you will drive governance, risk management, and adoption, coordinating with knowledge management and practice groups to ground AI solutions in real-world legal workflows.

Qualifications

• J.D. from an ABA-accredited law school and admission in good standing in at least one U.S. jurisdiction.
• Minimum 8 years of legal experience, including large law firm or major enterprise.
• Minimum 2 years focused on generative AI or legal technology, advising on or deploying AI-enabled solutions.
• Deep understanding of law firm workflows, quality expectations, and risk management.
• Experience working cross-functionally with product, engineering, and business stakeholders.
• Hands-on proficiency with generative AI tools and evaluating AI output quality.
• Knowledge of AI governance, confidentiality, and data privacy in legal practice.
• Ability to communicate complex legal/technical concepts to diverse audiences.

Responsibilities

• Serve as a senior legal SME for the AI Engineering team, applying practitioner insight to product development.
• Shape product requirements and prioritize work with AI Engineering leadership and Product Design & UX.
• Lead discovery with lawyers to identify opportunities for AI-enabled work (drafting, reviews, due diligence, research, summarization).
• Collaborate with UX and Engineering to ensure accurate, well-formatted outputs and usable interfaces.
• Lead legal-quality evaluation with rubrics, datasets, and test cases; improve prompts and model configuration.
• Incorporate firm expertise (precedents, templates, clause libraries) into AI products.
• Advocate for AI products, demonstrate use cases, and drive adoption and pilots.
• Embed responsible AI with governance, risk, and privacy considerations in product guardrails.
• Evaluate AI vendors/models and contribute to build-versus-buy decisions.
• Advance product practices through process improvements and knowledge sharing.

Skills

Cross-functional collaboration

Communication to diverse audiences

Organizational skills

Attention to detail

Interpersonal skills

Project management

Discretion/confidentiality

Analytical skills

Education

Juris Doctor (J.D.)

Admitted to at least one U.S. jurisdiction

Tools

Generative AI tools

RAG concepts

Agile delivery practices

Job description

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.

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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 [e-mail] (current employees should contact Human Resources).

Sidley Austin LLP is an Equal Opportunity Employer.