AI & Systems Administration Specialist/LAW
Winston Staffing
Job Description
Identifying high-value use cases, building AI-assisted workflows and prompt libraries, training attorneys and staff, and managing AI tool selection, administer core Firm systems: Active Directory/Microsoft 365 administration, patching, backups, and basic security operations. This is a hands-on, builder role — not a strategy-only position — -facing AI innovation and back-office systems-- MUST HAVE LAW firm experience
\n \n1. AI Tool & Workflow Development
\n• Design, build, and maintain AI-assisted workflows for recurring transactional tasks (e.g., first-pass lease and PSA review, loan document comparison, title/survey exception summarization, closing checklist generation, diligence memo drafting).
\n• Design, build, and maintain AI-assisted workflows for litigation tasks (e.g., deposition and document review support, chronology and timeline building, legal research synthesis, motion and brief drafting
\nassistance, e-discovery workflows).
\n• Develop, test, and version-control a firm prompt library and reusable templates, tailored to NY real estate and litigation practice, that produce reliable, attorney-usable output.
\n• Integrate AI tools with existing practice systems (document management, DMS/iManage or equivalent, billing/time entry, contract lifecycle tools) where appropriate.
\n2. AI Enablement & Training
\n• Train attorneys, paralegals, and staff — across both practice groups — on effective prompt construction, tool capabilities and limits, and practical use cases specific to their work.
\n• 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.
\n3. AI Governance, Ethics & Risk
\n• 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, and protection of privileged and work-product material (no client data enters non-vetted/consumer-grade tools).
\n• Professional responsibility: stay current on evolving guidance applicable to AI use by NY attorneys -.
\n• Accuracy controls: implement verification protocols to guard against hallucinated citations, misstated facts,
\nor unsupported numerical outputs before any AI-assisted work product reaches a client or a filing.
\n• Data governance: work with IT/security to vet new AI tools for data handling, retention, training-oncustomer-data practices, and vendor contract terms (including indemnification and IP ownership of outputs).
\n4. AI Tool & Vendor Evaluation
\n• Evaluate legal-AI vendors and platforms (e.g., contract analysis, litigation support, legal research, drafting assistants) via pilots and structured comparison against cost, accuracy, security posture, and integration effort.
\n• Maintain relationships with existing AI/legal-tech vendors and negotiate scope of pilots with Firm procurement.
\n5. AI Measurement & Reporting.
\n6. Systems Administration
\n• Administer Active Directory / Azure AD (or equivalent) user accounts, groups, and permissions; manage
\nMicrosoft 365 tenant administration (Exchange Online, Teams, SharePoint, OneDrive, Intune device
\nmanagement).
\n• Manage the Firm's Citrix environment (published apps/desktops, session hosts) to support secure remote and hybrid access to firm systems.
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