Position: Senior IT Training & Support Specialist
FLSA Status: Exempt
Reports to: Director of Information Technology
Education: Bachelor’s degree preferred
Experience: 6+ years of IT support and training experience in a corporate, professional services, or law firm environment
Salary: $90,000 – $110,000
Overview
A respected law firm in Chicago is seeking a Senior Training & Support Specialist to drive technology adoption and provide high-level user support across the firm. This role is responsible for designing and delivering impactful technical training programs while also providing hands-on desktop support to ensure attorneys and staff can effectively utilize the firm’s technology resources.
The ideal candidate brings a user-focused mindset, strong communication skills, and the ability to build trust across all levels of the organization. This individual will play a key role in improving productivity through training, troubleshooting, and ongoing support.
Key Responsibilities
• Design and deliver engaging, high-quality training programs to help users maximize technology tools and systems• Develop and maintain training materials for new applications, system upgrades, policies, and best practices
• Conduct onboarding training for new hires and provide ongoing one-on-one and group coaching
• Deliver in-person and virtual training sessions using video conferencing and collaboration tools
• Provide enterprise-level desktop support to attorneys, staff, and business professionals
• Diagnose, troubleshoot, and resolve hardware and software issues in a timely manner
• Configure, deploy, and support user devices including laptops, desktops, and mobile devices
• Track, document, and manage support requests through resolution, escalating issues as needed
• Assess user needs and technical proficiency to quickly identify and resolve issues
• Coordinate and schedule training initiatives across departments and promote technology best practices
• Contribute to internal knowledge bases and documentation resources
Qualifications
• 3+ years of experience training and supporting users within a law firm environment• Proven ability to educate and engage adult learners with varying levels of technical proficiency
• Strong hands-on experience with Windows 11 (or later), iOS, Android, and Microsoft Office (Word, Excel, PowerPoint, Outlook)
• Experience working with learning management systems to assign training and track participation
• Ability to create training content across multiple formats, including video, online, and interactive materials
• Excellent communication, presentation, and problem-solving skills
• Strong organizational skills with the ability to manage multiple priorities and support requests simultaneously
Preferred Experience
• Experience supporting and training on legal applications such as iManage, Westlaw, or similar platforms• Familiarity with Microsoft 365 and Teams administration, as well as audio-visual and video conferencing systems
• Experience with Active Directory, Group Policy, and PowerShell scripting
• Exposure to generative AI tools such as Copilot, CoCounsel, Claude, or Gemini
Why Scout Partners
Scout Partners delivers a highly personalized, relationship-driven approach to recruiting. We focus on aligning top talent with organizations where they can make an immediate and lasting impact. Our process is thoughtful, transparent, and built on long-term partnerships—ensuring the right fit for both our clients and candidates.