AI Legal Engineer

Holland & Knight; Chicago (IL); On-site; USD 150,000 - 224,000; Full time

Benefits offered by this job

Bonus opportunities

Comprehensive benefits

Paid holidays

Job summary

Holland & Knight is seeking an AI Legal Engineer to design, build, and operationalize AI-enabled workflows for the firm’s practice groups. You will partner with attorneys and knowledge management to translate needs into reliable tools that solve real legal problems.

You will work with the AI Product and Adoption teams to develop retrieval pipelines, documentation, and governance, while delivering training, playbooks, and ongoing support to ensure adoption and responsible use of AI across the

Qualifications

• Juris Doctor (JD) or equivalent legal background with 3–6+ years experience
• Experience designing or implementing AI/workflow solutions in a legal or professional services context
• Experience delivering training or onboarding to attorney/client-facing audiences

Responsibilities

• Design, build, test, and deploy AI legal workflows using firm-approved tools
• Identify high-value use cases with attorneys and map workflows
• Develop retrieval pipelines and document templates for reusable components
• Create evaluation frameworks to measure workflow quality, accuracy, and reliability
• Deliver trainings and enablement sessions to drive adoption
• Maintain playbooks and governance aligned with risk controls
• Track adoption and impact of deployed workflows

Skills

Prompt engineering

RAG pipelines

Workflow design

Stakeholder management

Training delivery

Education

Juris Doctor (JD) or equivalent

Tools

Harvey

Legora

Copilot

Job description

We are a Firm where people truly believe in what they do and strive to achieve the highest standards of performance and success.

This position can be based in our global operations centre in Tampa, FL, or at one of the Firm's offices: Atlanta, Austin, Birmingham, Boston, Century City, Charlotte, Chattanooga, Chicago, Dallas, Denver, Fort Lauderdale, Houston, Jacksonville, Los Angeles, Miami, Nashville, NewportBeach, NewYork, Orlando, Philadelphia, Portland, Richmond, SanFrancisco, Seattle, Tallahassee, Tysons, or Washington, D.C.

General Description

The AI Legal Engineer is responsible for partnering with subject matter experts to design, build, and operationalize AI-enabled workflows that solve concrete problems for the Firm's practice groups, and for equipping attorneys to build, refine, and govern their own workflows over time. This role pairs hands‑on workflow or skill development including prompt design, retrieval pipelines, document templates, evaluations, and guardrails with practice-group-facing training, enablement, and change management. The AI Legal Engineer will serve as a primary, trusted resource for our practice groups, supporting the successful rollout and sustained adoption of AI solutions and driving meaningful, long-term behavior change.

The AI Legal Engineer works closely with the AI Product team, AI Adoption team, the broader Knowledge & Innovation team, IT, the Innovation Practice Group, and Professional Development to translate attorney needs into reliable, repeatable AI solutions that deliver measurable value in daily legal work.

Key Responsibilities and Essential Job Functions

• Design, build, test, and deploy AI legal workflows and skills across firm-approved AI tools, supporting use cases such as contract review, due diligence, drafting, research, and summarization.
• Partner directly with attorneys and knowledge management professionals to identify high-value use cases, map workflows, and translate practice needs into structured AI solutions.
• Develop and maintain retrieval pipelines, document templates, and reusable workflow components with clear, attorney-ready documentation.
• Build and execute evaluation frameworks to measure workflow quality, accuracy, and reliability; monitor performance and iterate based on feedback and outcomes.
• Serve as a go-to resource for enablement and change management for developed workflows, partnering with the AI Adoption team to drive usage, deliver training sessions and workshops, 1:1 coaching, and develop practical playbooks and materials that support sustained adoption.
• Develop and scale best-practice standards, use‑case libraries, and playbooks that empower attorneys to responsibly and independently leverage AI tools while maintaining quality and risk controls.
• Embed human‑review checkpoints and audit mechanisms aligned with Firm governance, confidentiality, and professional responsibility requirements.
• Collaborate closely with cross‑functional stakeholders including the AI Product team, AI Adoption team, Knowledge & Innovation team, IT, Innovation Practice Group, and Professional Development to ensure aligned delivery and support.
• Track adoption, usage, and impact metrics for deployed workflows and recommend refinements or expansion opportunities.
• Manage ongoing maintenance of production workflows, including updates to prompts, retrieval sources, and guardrails in response to model and platform changes, user feedback, or evolving practice needs.
• Represent the AI Products & Adoption team in internal meetings, committees, and practice group sessions.
• Expected to maintain a regular and predictable work schedule and full attention to and engagement in work activities on behalf of the firm during business hours unless otherwise approved or required by applicable law.
• Special projects and duties as assigned.

Required Skills

• Demonstrated ability to design and build AI-enabled workflows in legal or professional‑services settings, including prompt engineering, retrieval‑augmented generation (RAG) concepts, and evaluation of model outputs.
• Working understanding of legal practice and attorney workflows, with the judgment to identify where AI is, and is not, appropriate.
• Strong interpersonal skills with experience building trusted relationships with attorneys, including partners and senior stakeholders.
• Clear, confident communicator able to teach AI concepts and workflow-building skills to non-technical legal audiences in practical terms.
• Comfort iterating in ambiguity: scoping a use case, building a prototype, gathering feedback, and refining toward a production-ready workflow.
• Strong attention to quality, accuracy, and risk; instinct to build in human‑review and verification steps for legal output.
• Consistently reliable, responsive, and solutions oriented.
• Working knowledge of the legal AI vendor landscape (e.g., Harvey, Legora, Microsoft Copilot, and similar) and familiarity with the components of modern AI workflow builders.
• Proficient in Microsoft Office Suite, or Microsoft 365.

Required Qualifications & Education

• Juris Doctor (JD) or equivalent legal background (e.g., practicing attorney, knowledge lawyer, paralegal with substantive practice experience) 3–6+ years of experience in legal, legal technology, knowledge management, practice innovation, or a comparable professional‑services environment.
• Demonstrated experience designing or implementing AI, automation, or workflow solutions in a legal or professional‑services context.
• Experience delivering training, enablement, or onboarding programs to attorney or client‑facing audiences.

Preferred Qualifications & Education

• Prior experience at an AmLaw firm, in‑house legal department, or legal technology company (e.g., Harvey, Legora, or similar).
• Hands‑on experience with workflow builders, prompt libraries, RAG pipelines, and AI evaluation methods.
• Familiarity with AI governance frameworks and emerging AI regulation relevant to legal practice.
• Light coding fluency (e.g., Python, SQL, or scripting) a plus but not required.

Physical Requirements

Ability to sit or stand for extended periods of time. Moderate or advanced keyboard usage. This position may be filled in multiple locations.

Salary and Benefits

In accordance with applicable Pay Transparency Laws, the pay range(s) for this position are listed below. These ranges may not be applicable to other locations. An individual's actual compensation will depend on the individual's qualifications and experience. In addition to the base compensation, Holland & Knight provides bonus opportunities and an exceptional benefits package.

• California, District of Columbia, Massachusetts: $163,000.00 - $245,000.00 per year
• Illinois, Washington, Tysons: $150,000.00 - $224,000.00 per year
• Colorado, Richmond: $136,000.00 - $204,000.00 per year

Benefits

• comprehensive medical (PPO and HDHPs)
• dental and vision plans including coverage for domestic partners
• life and AD&D insurance
• short and long term disability insurance
• tax-advantaged accounts for health care expenses, including FSAs and HSAs
• FSAs for dependent care
• health advocacy services
• behavioral health and counseling resources for all family members
• 401(k)
• profit sharing
• backup dependent care
• senior care planning support
• resources for individuals with development disabilities and their caregivers
• and paid holidays and other paid time off, including paid leave for new parents

Holland & Knight is an Equal Opportunity Employer and does not discriminate on the basis of race, color, religion, sex (including pregnancy, childbirth or related conditions, transgender status, and sexual orientation), national origin, age, disability, genetic information, veteran status or any other factor prohibited by law.

Applicants who are interested in applying for a position and require an accommodation during the process should contact [e-mail].

Personal Information collected from applicants will be used for the purpose of processing the application throughout any recruitment or employment process, as well as inclusion in a personnel file. Categories of data collected may include name, address, phone numbers, email, Social Security Number, and signature. Holland & Knight may collect further information if you consent to a background check. This includes criminal background, employment, and certifications. Please visit Legal Information Portal for Holland & Knight LLP’s privacy policies.

Holland & Knight is proud of having built one of the largest, most respected law firms in the world today. Holland & Knight has been advising clients for more than 130 years and has approximately 2,200 lawyers across the U.S. and in five international offices. Holland & Knight services clients globally. Known for our extraordinary legal service to clients, our culture of excellence, and our commitment to the communities in which we work, we are a firm of people who truly believe in what we do. We invite you to experience what Holland & Knight has to offer. It takes more than lawyers to build a great law firm and, as a result, the firm employs more than 1,700 business professionals. Business professionals play a pivotal role in the firm by planning and implementing strategic initiatives to enhance the firm’s capabilities and drive growth. The firm employs business professionals in many different areas, including technology innovation, pricing, business development, finance, talent acquisition, marketing, information governance, cybersecurity, information technology, talent development, compliance, office administration, communications, and project management, just to name a few. Additionally, the firm employs many paralegals and practice assistants who directly support our lawyers and clients. Together, these roles form the infrastructure that allows our lawyers to focus on providing exceptional client service.