Chicago - AI Adoption Specialist

About Us

At Winston Taylor, we set the standard, together.
Winston Taylor is a transatlantic law firm built for the businesses, people, and markets driving capital and innovation. Here, you're in the room. In the action. Sleeves rolled up. You'll work with leading clients. Disruptors. Fast-growth companies. And help them to stay one step ahead of the moment and make critical decisions that shape their future. We're present in the U.S., U.K., Europe, Latin America, and the Middle East, combining the scale and speed that clients demand. You'll be trusted with real responsibility from the outset and build experience through hands-on work. We take your progression personally. We provide the platform. You shape the work around your goals and aspirations. Step into the moments that matter. Join Winston Taylor.

Position summary

The AI Adoption Specialist supports attorneys and business professionals safely and effectively leveraging generative AI and other emerging technologies to improve quality, efficiency, and client outcomes. Working under the guidance of program leaders, this role collaborates with practice groups and business teams to learn workflows, help identify practical use cases, and assist with day-to-day enablement-training support, draft playbooks, communications, and hands-on user assistance-so users can integrate approved tools into their work. This role reports directly to the Director of Legal Technology & Innovation.This role helps reinforce responsible AI practices by promoting appropriate data handling, confidentiality, and human oversight; supporting governance and risk-aligned adoption efforts; and contributing to impact tracking and continuous improvement.

Position responsibilities

• Support GenAI adoption efforts: Execute adoption plans and own day-to-day enablement activities that help drive safe, effective adoption of approved generative AI tools and related workflows-during implementation and at scale-including user guidance on appropriate use, human review, and value measurement.
• Collaborate with practice groups and cross-functional teams: Engage with practice groups to understand matter and business workflows, help identify GenAI opportunities and adoption barriers, and assist with tailoring enablement approaches that align with risk, confidentiality, and client requirements.
• Engage stakeholders and users: B uild and maintain relationships with stakeholders to set expectations, explain GenAI capabilities and limitations, and encourage responsible adoption. Assist with documenting and sharing vetted use cases (and anti-patterns) that demonstrate value while protecting client confidentiality and firm data.
• Support and conduct workshops to enable AI-enabled work: Assist with developing and facilitating workshops that build practical skills (e.g., prompt techniques, iterating safely, verifying outputs, citing sources where appropriate) and confidence to integrate GenAI into drafting, research, analysis, and knowledge work with appropriate attorney oversight.
• Help develop and maintain responsible AI enablement materials: Develop and update resources-guides, playbooks, training assets, FAQs, and best practices-that help users get started and mature over time, including guardrails for confidentiality, data classification, attribution, and human-in-the-loop review.
• Communication and change management: Develop and deliver targeted communications that explain benefits, constraints, and approved ways of using GenAI tools. Assist with identifying and enabling champions to share safe success stories, reinforce standards, and accelerate adoption through peer learning.
• User onboarding: Implement role-based onboarding pathways that help individuals and teams begin using approved GenAI tools safely, including just-in-time training, recommended starter use-cases, and reminders on confidentiality, verification, and escalation routes for questions or issues.
• User training: Facilitate and deliver structured adoption programs that encourage consistent use of legal technology and generative AI, with emphasis on prompt discipline, output validation, bias/hallucination awareness, and quality control.
• Adoption and value metrics: Track and summarize adoption, user engagement, and feedback to support program reporting and continuous improvement. Assist with monitoring usage (e.g., access frequency, feature utilization) and outcomes (e.g., time saved, quality improvements, client impact), and escalate potential risk signals (e.g., misuse patterns) to appropriate stakeholders.
• Stay informed of product developments: Stay current on enhancements to firm-approved GenAI and legal technology solutions and help update guidance and training materials as new features are introduced.
• Improve AI-enabled user experiences. Provide actionable feedback, adoption barriers, and risk learnings with Information Services teams (e.g., Practice Innovation, Knowledge, Risk, Security, and IT) to support enhancements and help improve usability, value realization, and compliance with firm standards.

Experience, skills, and qualifications

• Bachelor's degree required, JD a plus.
• 3+ years of experience in legal technology adoption, change management, digital transformation or technology enablement, including supporting end users with digital tools (preferably AI-driven) in a governed environment required.
• Must live within a commutable distance to the applicable firm office with the ability to come into the office 3-4 days per week.
• The ideal candidate brings strong legal-technology interest, a learning mindset, and clear communication skills, with a passion for helping others adopt new capabilities while protecting the firm and its clients.
• Experience in legal practice, legal operations, and/or legal service delivery preferred; familiarity with responsible AI concepts (privacy, confidentiality, model limitations, and human oversight) strongly preferred.
• Working knowledge of legal technology, collaboration tools, and generative AI capabilities and limitations in professional services (or demonstrated ability to learn quickly).
• Proficiency in creating clear guidance, communications, presentations, and playbooks that translate GenAI concepts into practical, role-based ways of working.
• Excellent communication and interpersonal skills with an ability to engage and inspire users across all levels of the firm to adopt GenAI responsibly.
• Ability to support change and adoption activities that drive measurable value while reinforcing governance, confidentiality, and quality standards.
• An attorney-centric approach focused on understanding user needs, pain points, and motivations to ensure GenAI-enabled workflows are relevant, intuitive, and impactful.
• Analytical skills to interpret adoption metrics and user feedback, evaluate outcomes and risks (e.g., quality, accuracy, and misuse patterns), and translate insights into actionable improvement strategies.
• Problem-solving skills to address adoption challenges, improve prompts/workflows, and mitigate responsible-AI and confidentiality risks in partnership with stakeholders.
• Ability to work collaboratively with cross-functional teams (e.g., Practice Innovation, Knowledge, Risk, Security, and IT) to deliver governed GenAI solutions and enablement.
• Strong organizational skills, including coordinating multiple enablement tasks and stakeholder inputs while maintaining attention to detail.

BENEFITS

Winston offers comprehensive benefits that provide a full spectrum of coverage and support for our full-time employees and their families. Additional information about benefits and rewards can be found here.

SALARY

Illinois applicants only: The target annual salary range for this role is currently $113,000-$147,000 based on a regular, full-time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.

New York applicants only: The target annual salary range for this role is currently $125,000-$160,000 based on a regular, full-time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus. Washington, DC applicants only: The target annual salary range for this role is currently $120,000-$155,000 based on a regular, full-time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.

We are an equal opportunity employer and welcome applicants from all backgrounds and experiences. #LI-DC2