AI Transformation & Learning Associate Director

Sidley Austin•Chicago, IL

1d•$185,000 - $225,000•Hybrid

About The Position

The AI Transformation & Learning Associate Director is responsible for building and scaling Sidley’s firmwide AI enablement strategy — equipping lawyers and business professionals to confidently and responsibly use AI in their daily work. This role sits at the center of the Firm’s AI transformation, shaping how AI is adopted across practices, influencing leadership, and positioning Sidley as a market leader in responsible AI. The role blends responsible AI governance, change management, instructional design, and executive communication to drive practical AI proficiency across the Firm. This leader will design and lead a best-in-class AI enablement program; create audience-specific engagement programs; embed Responsible AI standards in all training; and represent Sidley externally with clients and at industry forums. The role partners with senior stakeholders across Legal, Compliance, and Technology, and collaborates with Learning and Development, Knowledge Management, and 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 a liberal arts, technology, or related field; or equivalent work experience.
A minimum of 7 years of relevant professional experience.
Demonstrated experience creating curricula and teaching technical topics to non-technical audiences.
Strong facilitation skills and polished executive/client presentation skills.
Hands-on expertise with AI platforms (e.g., OpenAI, Anthropic) and prompt-engineering and RAG concepts.
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
Applicants must be authorized to work in the United States without the need for employer sponsorship, now or in the future

Nice To Haves

Experience with program measurement and analytics; familiarity with BI tools (Power BI/Tableau) or light scripting (e.g., Python) is a plus.

Responsibilities

Develop and drive the AI enablement 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 expert 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.
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 enablement 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 enablement 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 and 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.