AI Literacy Associate Director

Sidley Austin LLP • Chicago, IL

3d • Hybrid

About The Position

AI Literacy Associate Director is responsible for designing, launching, and continuously improving Sidley’s firmwide AI Literacy program for lawyers and business professionals. The role blends responsible AI governance, change management, instructional design and executive communication to scale practical AI proficiency across the Firm. This leader will create audience-specific engagement programs; embed Responsible AI standards in all training; collaborate with OGC and Sidley Compliance on policies and represent Sidley’s program externally with clients and at public forums. The role will collaborate internally with the Data and AI department and operate as a subject matter expert who partners closely with Learning and Development, Knowledge Management, Information Security & Privacy. The ideal candidate demonstrates polished executive presence and can deliver compelling presentations and demos to partners, Firm leadership, and clients.

Requirements

• Bachelor’s degree in liberal arts field, technology field or other related field; or equivalent work experience.
• A minimum of 7 years of relevant professional experience in the legal or professional services industry, including substantial experience working in a law firm, as well as experience applying AI technologies to legal use cases.
• Demonstrated experience creating curricula and teaching technical topics to non-technical audiences.
• Strong facilitation skills and polished executive/client presentation skills.
• Working knowledge of Responsible AI policy and AI governance in professional services.
• Experience collaborating with Legal, Information Security & Privacy, Compliance, Marketing/BD, and IT teams.
• Experience leading change management initiatives, including stakeholder engagement, communication planning, and adoption strategies for technology or innovation programs.
• Strong organizational skills
• Strong attention to detail
• Good judgment
• Strong interpersonal communication skills
• Strong analytical and problem-solving skills
• Able to work harmoniously and effectively with others
• Able to preserve confidentiality and exercise discretion
• Able to work under pressure
• Able to manage multiple projects with competing deadlines and priorities

Nice To Haves

• Advanced degree such as JD or Masters in a related field.
• Hands-on familiarity with AI platforms (e.g., ChatGPT/OpenAI, Anthropic, Microsoft Copilot, Google Gemini) and prompt-engineering and RAG concepts.
• Familiarity with the opportunities and challenges specific to AI in the legal field
• Certifications such as CPTD, Prosci, PMP, or recognized Responsible AI credentials.
• Experience with program measurement and analytics; familiarity with BI tools (Power BI/Tableau) or light scripting (e.g., Python) is a plus.
• Experience applying change management frameworks (ADKAR, Kotter, Lewin) in professional services settings.

Responsibilities

• Develop and drive the AI Literacy vision, roadmap, and operating plan; define learning objectives and proficiency levels by audience (attorneys, staff, leadership, practice groups) in direct support of firm approved AI tools in collaboration with the Knowledge Management and Learning and Development teams.
• Organize, grow and build engagement programs: internal communications, adoption campaigns, practice-tailored playbooks, a network of AI Champions, and a community of practice
• Act as a subject matter experting working with internal teams to drive the design and production of curricula (101 through advanced) utilizing standard firm messaging channels and platforms, including live workshops, e-learning modules, microlearning, simulations, office hours, and a searchable content library.
• In partnership with the Office of General Counsel, define and operationalize Responsible AI at Sidley; codify principles, acceptable-use guidelines, risk controls, data-handling and confidentiality standards; e, InfoSec/Privacy, and Compliance.
• Partner with Learning & Development to deliver content via the Firm’s LMS; track completions, assessments, CLE eligibility, and certification pathways where applicable.
• Coordinate with Product Management and Engineering on AI tool rollouts; help ensure enablement content (prompting standards, configuration tips, use-case guides) is current and consistent with AI Literacy messaging.
• Coordinate with internal teams to develop adoption and impact metrics.
• As needed, partner with Marketing and Communications teams to create client-facing materials and present Sidley’s AI Literacy and Responsible AI approach to clients; partner with Marketing/BD for proposals, thought leadership, and events.
• Deliver polished presentations to partners, committees, leadership, and client audiences.
• Maintain awareness of developments in generative AI, legal technology, and AI governance/regulation; translate changes into timely updates to policies, playbooks, and curricula.
• Participate in authoring practical guidance (prompting standards, model selection, risk triage workflows, data retention) and ensure accessibility for global audiences.
• Other duties as needed.

Benefits

• Our compensation package also includes bonus eligibility and a comprehensive benefits program.
• Benefits information can be found at Sidley.com/Benefits

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 1,001-5,000 employees