Digital Learning AI Enablement Lead

Sidley Austin LLP (IL LLP); Chicago (IL); Hybrid; USD 107,000 - 137,000; Full time

Benefits offered by this job

Bonus eligibility

Job summary

Sidley Austin LLP in Chicago seeks an AI Enablement Lead to design, build, and maintain AI-assisted workflows for learning and technology adoption across the Firm. You will blend instructional design, adult learning theory, and practical technical skills to improve repeatable processes, document workflows, and support effective use of AI tools.

Responsibilities include partnering with teams, reviewing AI-generated content for quality, creating workshops, and developing reports on adoption and

Qualifications

• Bachelor’s degree or equivalent work experience.
• Minimum of five years of experience in learning and development, instructional design, learning technology, or a related field.
• Minimum of one year of hands-on experience designing, building, testing, documenting, and maintaining AI-assisted workflows intended for use by others.
• In‑depth knowledge of instructional design, adult learning principles, and learning technology.
• Demonstrated experience using generative AI tools, such as ChatGPT, Claude, or Copilot, including prompt design, workflow development, output evaluation, and assessment of appropriate AI use cases.
• Strong data analysis and reporting skills, including advanced proficiency in Microsoft Excel and proficiency with Microsoft Office applications.
• Strong written communication skills, including the ability to develop clear documentation and instructions for end users.

Responsibilities

• Design, build, test, and maintain AI-assisted workflows, tools, and automations that improve the development, delivery, and measurement of learning and technology adoption programs.
• Partner with Digital Learning team members to identify opportunities for AI-enabled process improvement and refine workflows based on business needs.
• Review AI-generated learning content to ensure instructional soundness, accuracy, and alignment with Firm standards.
• Apply instructional design and adult learning principles to AI-assisted solutions and maintain content standards.
• Document AI-assisted workflows, inputs, processes, outputs, limitations, and appropriate use for team adoption.
• Maintain the team’s library of AI-assisted tools and workflows and recommend improvements as technologies evolve.
• Provide guidance, coaching, and workshops on effective use of AI tools and techniques.
• Develop reporting on learning and technology adoption activity to support evaluation and continuous improvement.

Skills

Instructional design

Adult learning principles

Data analysis

Written communication

Education

Bachelor’s degree or equivalent work experience

Tools

Excel

Power Automate

Python

APIs

SCORM

Job description

The Digital Learning AI Enablement Lead designs, builds, and maintains AI-assisted workflows that enhance the development, delivery, and measurement of learning and technology adoption programs across the Firm. As an emerging expert in AI-assisted learning solutions, the Lead combines knowledge of instructional design, adult learning principles, and learning technology with hands‑on technical expertise to improve repeatable processes, develop reliable and documented workflows, and support the effective use of AI tools across the Digital Learning team and broader Learning & Development function.

Duties and Responsibilities

• Design, build, test, and maintain AI-assisted workflows, tools, and automations that improve the development, delivery, and measurement of learning and technology adoption programs.
• Partner with Digital Learning team members to identify appropriate opportunities for AI-enabled process improvement, define requirements, develop solutions, and refine workflows based on business needs and user feedback.
• Review AI-generated learning content, including outlines, scripts, job aids, assessments, and course descriptions, to ensure instructional soundness, accuracy, consistency, and alignment with Firm standards.
• Apply instructional design and adult learning principles to AI-assisted solutions and maintain the content standards, templates, and conventions used to support consistent learning outputs.
• Document AI-assisted workflows, including required inputs, processes, expected outputs, limitations, and appropriate use, enabling team members to use solutions effectively and independently.
• Maintain the team's library of AI-assisted tools and workflows, monitoring utilization and effectiveness and recommending improvements, replacements, or retirement as technologies, source data, and Firm platforms evolve.
• Provide guidance, coaching, troubleshooting, and working sessions to Learning & Development colleagues on the effective and appropriate use of AI tools and techniques.
• Facilitate AI enablement workshops and digital learning programs through classroom and virtual instruction, software demonstrations, workshops, and individual coaching, incorporating feedback to improve effectiveness.
• Develop and maintain reporting on learning and technology adoption activity, including completion, utilization, engagement, and learner feedback, to support evaluation and continuous improvement.
• Collaborate with colleagues across Learning & Development, Data & AI, IT, Knowledge Management, and other functions to support alignment with Firm AI initiatives and contribute to related learning projects as business needs evolve.

Education and/or Experience

• Bachelor’s degree or equivalent work experience.
• Minimum of five years of experience in learning and development, instructional design, learning technology, or a related field.
• Minimum of one year of hands‑on experience designing, building, testing, documenting, and maintaining AI-assisted workflows intended for use by others.
• In‑depth knowledge of instructional design, adult learning principles, and learning technology.
• Demonstrated experience using generative AI tools, such as ChatGPT, Claude, or Copilot, including prompt design, workflow development, output evaluation, and assessment of appropriate AI use cases.
• Strong data analysis and reporting skills, including advanced proficiency in Microsoft Excel and proficiency with Microsoft Office applications.
• Strong written communication skills, including the ability to develop clear documentation and instructions for end users.

Preferred

• Experience administering or reporting from a learning management system; Cornerstone OnDemand preferred.
• Experience with scripting, APIs, structured data, or low‑code automation technologies such as Python, JavaScript, or Power Automate.
• Experience with e‑learning authoring tools and SCORM packaging.
• Experience measuring learning or technology adoption outcomes.
• Experience in a law firm or other professional services environment.

Other Skills and Abilities

• 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

#LI-Hybrid #LI-OE1 Applicants must be authorized to work in the United States without the need for employer sponsorship, now or in the future

The target salary range for this role is: $107,000 - $137,000 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.

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

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.