Senior Training and Support Specialist

Esquire Recruiting, LLC
Chicago, IL

Position: Sr. Training & Support Specialist

FLSA Status: Exempt

Reports to: Director of Information Technology

Education: Bachelor’s degree preferred.

Experience: 6+ years of experience in IT support and training in a corporate, professional services, or law firm environment.


Our prestigious and highly regarded law firm client is seeking an IT Training & Support Specialist who will primarily be responsible for designing and delivering effective, high-quality technical training. In addition, this position provides enterprise-level desktop training and support to all members of the organization. The role requires building strong trust with the firm’s IT users through a friendly and positive approach, ensuring solutions to technical problems are provided in a timely and accurate manner.


Job Duties & Responsibilities

  • Deliver comprehensive, effective, and timely training to equip personnel to use firm technology productively and efficiently.
  • Design, develop, and implement training courses and materials for new applications, technologies, policies, and best practices.
  • Provide training for new hires, upgrades, and offer one-on-one or group coaching focused on productivity.
  • Offer enterprise-level assistance and training to attorneys, paralegals, and other professionals, both in person and through video and web conferencing technologies.
  • Diagnose, troubleshoot, and resolve software and hardware issues, and assist users with installing and maintaining applications and programs.
  • Configure and deploy user endpoints, including laptops, desktops, and mobile devices.
  • Track system issues through to resolution, ensure all issues are properly logged, and escalate unresolved issues to the appropriate individuals.
  • Assess user skills, ask targeted questions to quickly identify the root of support problems, and provide prompt and accurate feedback.
  • Coordinate and schedule training for all personnel and promote technology best practices among individuals and practice groups.
  • Contribute to internal knowledge bases and document technical knowledge in the form of notes and manuals.


  • Requirements
  • 3+ years of experience training and supporting users in a law firm environment.
  • Ability to educate and motivate adult learners with varying levels of computer
  • experience and present subject matter clearly.
  • Hands-on experience with business desktop and mobile environments, specifically Microsoft Windows 11 (or above), iOS, Android, and the MS Office Suite (Word, Excel, PowerPoint, Outlook).
  • Familiarity with implementing and using a learning management system to create learning plans, assign classes, and track attendance.
  • Experience creating training materials across various media, including online, video, and interactive formats.
  • Excellent public speaking, personal interaction, problem-solving, and communication skills.
  • Ability to prioritize and manage multiple projects and open help desk issues simultaneously.
  • Preferred Skills
  • Experience training legal-related desktop applications such as iManage, Westlaw, and other legal research platforms.
  • Experience with Microsoft 365/Teams administration, audio-visual, VOIP, and video conferencing systems is a plus.
  • Experience with MS Active Directory, Group Policy, and PowerShell scripting is a plus.
  • Experience with generative AI toolsets such as CoPilot, CoCounsel, Claude, and Gemini.
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