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Direcor of Legal AI, Training and Automation
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Confidential
Pittsburgh, PA (In Person)
Full-Time
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Job Description
Law firm in downtown Pittsburgh is seeking a Director of Legal AI, Training and Automation to help advance how our attorneys and professional staff use technology in a high-volume, multi-office litigation and transactional practice. This leadership role will focus on practical AI deployment, workflow improvement, training, and efficient, results-oriented service across the firm. This position will help translate emerging technology into stronger work product, better collaboration, and greater value for our clients. The ideal candidate is a professional with strong law firm operations knowledge, experience supporting legal teams, and a track record of implementing practical AI and workflow solutions in a professional services environment. This person should be able to:
- Understand litigation workflows from intake through trial, including insurance defense and other high-volume practices
- Build practical systems and workflows for multiple practice areas and business uses, not just recommend software
- Train attorneys and staff and work effectively across offices, practice groups, and administrative teams
Responsibilities Include:
Automation and AI Development Design and deploy AI-enabled systems that support the firm's workflows across offices and practice groups.- Identify existing legal and business processes ideal for automation and application of AI tools, focusing on ROI, personnel efficiency, and increased accuracy
- Build AI solutions for attorneys and staff in different practice areas and business departments including those related to reports, memos, motions, discovery, correspondence, trial materials, contracts, and corporate documents
- Create reusable templates, prompts, agents, and workflow tools that can scale across the firm Billing Efficiency and Carrier Compliance Improve revenue capture and reduce write-offs through standardized, AI-assisted billing workflows aligned with carrier and client expectations.
- Standardize billing narratives and workflow support aligned with carrier guidelines and client requirements
- Automate conversion of work activity into billing-ready entries and identify incomplete or non-compliant time entries
- Use AI to generate clear, defensible billing support from emails, meetings, and work product Trial Preparation and Litigation Intelligence Deploy AI tools that improve trial readiness, case analysis, and strategic decision-making.
- Identify inconsistencies, admissions, expert vulnerabilities, and key themes in testimony and case materials
- Generate draft examination outlines, witness preparation materials, chronologies, and mediation support
- Turn transcripts, pleadings, medical records, and case materials into usable summaries, chronologies, timelines, and issue-tagged work product
- Help litigation teams work through large volumes of information more efficiently and consistently Training and Adoption Drive practical AI adoption across the firm through training, support, and measurable workflow improvement.
- Design and deliver AI fluency training to ensure attorneys and staff have foundational knowledge on AI usage, risks, legal ethics, and responsible use
- Design and deliver legal-focused training for Microsoft Copilot, Lexis Protégé, iManage, CaseMap and related workflows
- Train attorneys and staff to turn existing documents and large files into usable drafts, summaries, and analysis
- Provide ongoing support focused on practical user needs and adoption barriers Tool Selection, Integration and Governance Help the firm select, deploy, and govern the right tools without adding unnecessary complexity or risk.
- Evaluate and implement drafting, transcript analysis, medical summarization, and workflow automation tools that fit firm needs
- Leverage existing platforms before recommending new software purchases
- Develop practical guardrails for confidentiality, privilege, data handling, cost-control, and attorney review of AI output
- Advise on AI use and governance policies for attorneys and staff. Required Qualifications
- Experience building or implementing AI tools, automations, or workflow systems in a law firm or professional services environment
- Strong understanding of generative AI, large language models, and workflow design
- Hands-on experience with Microsoft 365 Copilot, Power Automate, Power Apps, workflow automation tools, and prompt development
- Ability to work directly with attorneys, practice leaders, and administrative teams to translate needs into practical solutions Preferred Qualifications
- Experience supporting defense litigation, insurance law, or other high-volume legal practices
- Familiarity with iManage, Lexis Protégé, or similar legal technology platforms
- Experience with API integrations, document automation, knowledge management, or multi-office rollout projects