Legal Technology/AI Specialist
Winston Staffing
3+ years of experience implementing AI or legal-technology solutions in a law firm, corporate setting. Demonstrated hands-on experience with large language model tools (e.g., ChatGPT Enterprise, Microsoft Copilot, Claude, Harvey, CoCounsel
• Design, build, and maintain AI-assisted workflows for recurring transactional tasks
• Develop, test, and version-control a firm prompt library and reusable templates
• Integrate AI tools with existing practice systems (document management, DMS/iManage or equivalent,
• Train attorneys, paralegals, and staff — across both practice groups
• Create internal documentation, quick-reference guides, and recorded trainings; run office hours and onboarding for new hires.
• Act as first-line resource for attorneys experimenting with AI on a matter, including advising on when a use case is appropriate to attempt versus better left to traditional methods.
AI Governance, Ethics & Risk
• Confidentiality and privilege: ensure AI tools and workflows are configured and used in a manner
consistent with client confidentiality obligations, joint-defense/common-interest considerations,
• Evaluate legal-AI vendors and platforms (e.g., contract analysis, litigation support, legal research,
Maintain relationships with existing AI/legal-tech vendors and negotiate scope of pilots with Firm
procurement.
Systems Administration
• Administer Active Directory / Azure AD (or equivalent) user accounts, groups, and permissions; manage
Microsoft 365 tenant administration (Exchange Online, Teams, SharePoint, OneDrive, Intune device
management).
• Manage the Firm's Citrix environment (published apps/desktops, session hosts) to support secure remote
• Administer VMware virtualized server infrastructure (ESXi/vCenter), including provisioning, monitoring,
• Use Microsoft Endpoint Configuration Manager (SCCM) for OS imaging, application deployment,
• Apply security patches and software updates across endpoints and core servers on a regular cadence;
IT Security & Compliance
• Working knowledge of Microsoft 365 administration (Exchange Online, Teams, SharePoint/OneDrive)
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