Generative Ai Testing Jobs in Chicago, IL (NOW HIRING)

About Kirkland & Ellis
At Kirkland & Ellis, we don't just meet the standard for legal excellence - we set it. Our culture is built on teamwork, ingenuity and an unwavering commitment to continuous growth. We tackle the most sophisticated legal challenges with bold ideas and innovative solutions, powered by the exceptional experience and ambition of our 7,000+ people, including 4,000+ attorneys, across 24 offices worldwide. Our dedicated professionals share our lawyers' commitment to excellence and show up each day to do meaningful work that helps drive global business, investment and innovation forward.
What You'll Do
As an AI Advisor you will embed within practice groups to translate legal tasks and workflows into scoped AI solutions, owning end-to-end workflow development, partnering with engineers, and contributing to a scalable playbook of best practices. In addition to internal firm initiatives, this role may support client-facing matters, partnering with practice teams to deliver AI-enhanced legal services directly to clients. You will also champion responsible AI adoption, designing training that empowers attorneys to use these tools with confidence.
The ideal candidate is equal parts trusted advisor and hands-on builder, someone who thrives on rapid experimentation and translates complex challenges into high-impact solutions.
The AI Advisor sits within the Innovation Program AI Advisory Services team, partnering with directors, engineers, data scientists and project managers to deliver transformative outcomes for practice teams and clients. Reporting through matrixed management to the Associate Director of Innovation Engineering, this role bridges legal expertise and cutting-edge AI capability.
Practice Group Engagement
• Act as a credible, authoritative advisor on AI workflow and integration strategy, guiding attorneys on where and how AI can add value across their practices.
• Embed within litigation and transactional practice groups to document current-state workflows with sufficient specificity to drive enhanced design translating attorney tasks and needs into scoped requirements and flagging opportunities to leverage existing builds or address known failure points.
• Support client engagements by partnering with practice teams to deliver AI-assisted legal services directly to clients, maintaining the quality and professional standards expected in client-facing work.
• Champion responsible AI adoption by ensuring attorneys understand generative AI capabilities, limitations, and firm governance requirements.
• Coordinate tasks, timelines, and stakeholders for AI workflow development initiatives.
Workflow Development & Testing
• Own end-to-end AI legal workflow development-decomposing complex legal tasks, designing and testing prompts, aligning outputs to firm standards, and iterating rapidly across platforms.
• Design and execute testing protocols, including prompt engineering, output benchmarking, and iterative attorney-driven refinement, while maintaining structured decision logs that capture each workflow's task requirements, prompt logic, validation criteria, failure modes, and platform constraints with sufficient specificity to reconstruct workflows on future infrastructure.
• Partner with engineers as workflows mature, bridging attorney domain knowledge and technical execution while building deeper technical fluency through exposure to pipeline design and failure analysis.
Playbook & Training
• Contribute to a scalable AI workflow playbook codifying best practices, templates, decision trees, and implementation guides.
• Provide informed recommendations on AI tools, capabilities, and roadmaps grounded in direct legal practice experience. Proactively share learnings and emerging patterns across the team.
• Collaborative across training and development teams to design and deliver attorney training programs-including demonstrations, user guides, and feedback mechanisms-for effective AI tool use and workflow adoption.
• Track and report project status, adoption metrics, and outcomes to Innovation leadership.
• Stay current on AI developments, regulatory changes, and industry best practices.
What You'll Bring
Required
• A J.D. from an accredited law school is strongly preferred; however, candidates who do not hold a law degree but possess five or more years of demonstrated experience leading innovation initiatives, driving technology adoption, or overseeing AI implementation at a large law firm or legal technology company will also be given strong consideration.
• Comfort operating in a billable, client-service environment, with an understanding of the pace, quality expectations, and confidentiality requirements associated with delivering work product directly to clients.
• Strong aptitude for process improvement and legal technology, including generative AI/large language models with sufficient understanding of where AI succeeds and fails to engage both legal teams and engineers.
• Direct experience with legal AI platforms (Harvey, Legora, CoCounsel, Lexis+ AI, or comparable), including hands-on building and iterating on prompts and workflows with accountability for output quality.
• Ability to collaborate with attorneys and leadership at all levels, establishing credibility with senior stakeholders and influencing decisions in fast-moving, ambiguous environments with firsthand understanding of attorney pressures, pace and quality expectations.
• Strong writing, project management, and organizational skills with sound judgment - able to manage multiple concurrent initiatives, lead and document design calls, translate technical concepts for varied audiences, and independently advance priorities.
• Collaborative and adaptable team player who tackles challenges with initiative, creativity, and accountability, bringing a client-focused, solutions-oriented mindset.
Preferred
• J.D. from an accredited law school.
• Three (3) years of experience as an attorney at an AMLAW 50 firm or comparable legal environment.
• Experience training legal teams on new tools, including developing educational materials or governance policies.
• Knowledge of data security, information governance, and compliance best practices for AI and legal technology.
Compensation
The base salary range below represents the low and high end of the salary range for this position in each of the below locations. This range may differ based on your geographic location and cost of living considerations. At Kirkland & Ellis, we consider compensation more than just a base salary. We offer an exceptional range of flexible benefits including comprehensive healthcare, paid time off, and retirement. We also offer personal support and tailored learning and development opportunities all designed to help you realize your full potential both in life and at work.
Compensation Range:
Chicago: $153,000 - $191,000
New York: $153,000 - $211,000
Los Angeles: $153,000 - $211,000
Washington D.C.: $153,000 - $211,000
Bay Area: $153,000 - $220,000
How to Apply
Thank you for your interest in Kirkland & Ellis LLP. To complete an application and submit your resume, please click "Apply Now."
Don't meet every job requirement? That's okay! If you're excited about this role but your experience doesn't perfectly fit every qualification, we encourage you to apply anyway. You may be just the right person for this role or others at Kirkland.
Equal Employment Opportunity
All employment decisions, including the recruiting, hiring, placement, training availability, promotion, compensation, evaluation, disciplinary actions, and termination of employment (if necessary) are made without regard to the employee's race, color, creed, religion, sex, pregnancy or childbirth, personal appearance, family responsibilities, sexual orientation or preference, gender identity, political affiliation, source of income, place of residence, national or ethnic origin, ancestry, age, marital status, military veteran status, unfavorable discharge from military service, physical or mental disability, or on any other basis prohibited by applicable law. #LI-Hybrid #LI-AR1