Technology Training Manager Jobs in Chicago, IL (NOW HIRING)

About The Firm

Amundsen Davis, LLC is a full‑service business law firm with 260 attorneys. Headquartered in Chicago, we are one of the fastest‑growing law firms in the Midwest. We understand the entrepreneurial mindset that drives our clients’ business decisions, and we use this insight to respond to their needs creatively, efficiently, and pragmatically. Our firm handles the transactional, labor and employment, and litigation needs of companies across the United States. With deep experience in both litigated and transactional matters, we offer a uniquely well‑rounded partnership for your business. Amundsen Davis has offices in: Chicago, Crystal Lake, St. Charles, and Rockford, IL; Cleveland and Columbus, OH; Milwaukee, Appleton, Brookfield, Green Bay, and Madison, WI; St. Louis, MO; and Indianapolis, IN.

Position Overview

The Technology Training Specialist is responsible for designing, developing, and delivering high quality technology training programs for attorneys, staff, and other end users across multiple firm locations. This role serves as a critical liaison between the IT department and the business, ensuring technology solutions are effectively adopted, supported, and aligned with firm workflows and business objectives.

In addition to instructor led training, the Technology Training Specialist is responsible for developing scalable learning resources including eLearning content, instructional videos, knowledge articles, and self-service learning experiences. The role will help support the continued growth and evolution of the firm's technology training program by leveraging learning technologies, user feedback, and adoption metrics to improve the end user experience.

This position may occasionally require additional hours, including evenings and weekends, to meet training needs or support firm-wide initiatives.

Primary Duties and Responsibilities

• Design and deliver IT training and new hire orientation programs for attorneys and
• Develop and maintain self-paced learning content, instructional videos, digital learning resources, and eLearning modules that support technology adoption and ongoing user education.
• Serve as a Learning Management System (LMS) administrator, managing course creation, learner enrollment, learning paths, reporting, and platform optimization.
• Develop learning pathways and training programs that provide users with accessible, on demand learning opportunities.
• Measure training effectiveness through learner feedback, participation metrics, adoption trends, and Service Desk data (Fresh Service Application).
• Conduct group and one-on-one training sessions, both in-person and remotely via webinars or video conferencing.
• Respond to ad hoc training requests and tailor sessions to specific user needs.
• Provide user feedback to IT teams on technology solutions and assist in refining tools and processes.
• Collaborate with Infrastructure and Applications teams to ensure training aligns with current systems and updates.
• Partner with IT and firm leadership to identify training priorities, promote strategic initiatives, and modernize training delivery through digital learning experiences and knowledge management resources.
• Support firmwide technology rollouts and enhancements through structured training and user readiness efforts

User Engagement, Adoption, and Continuous Learning

• Establish regular, informal connections with users outside of scheduled training sessions to build rapport and offer ongoing support.
• Host “Drop-in Tech Training Office Hours,” quick Q&A huddles, or drop-in sessions to provide accessible help and foster a culture of continuous learning.
• Share bite-sized content such as quick tips, “Did You Know?” posts, and short videos to keep users engaged and informed.
• Maintain a friendly and welcoming presence, encouraging users to reach out with questions or feedback.
• Review Service Desk requests to identify recurring issues and training gaps, and proactively engage users with targeted education and support.

Cross Functional IT Team Collaboration

• Review Service Desk requests to identify recurring issues and training gaps, and proactively engage users with targeted education and support.
• Provide application-specific support and “how-to” assistance, documenting resolutions in the incident management system.
• Escalate complex support issues to appropriate internal teams.
• Collaborate with the IT Service Desk to share knowledge and improve first-level support
• Participate in change management and continuous service improvement initiatives.
• Contribute to the development of support plans and training documentation
• Ability to support users with varying levels of technical proficiency.
• Proactively collaborate and share knowledge and learnings from user feedback with the broader IT team.

Education and Experience

• Bachelor’s degree in Computer Science, MIS, or a related field, or equivalent work
• 3+ years of experience as an IT Trainer, preferably in a legal or professional services environment.
• Experience delivering training in classroom, one-on-one and remote settings.
• Experience implementing, administering, or optimizing Learning Management Systems (LMS) and eLearning platforms preferred.
• Experience creating interactive eLearning content using instructional design methodologies and authoring tools preferred.

Knowledge, Skills, and Abilities

• Proven experience in developing and delivering training in classroom, one-on-one, and remote settings.
• Knowledge of adult learning principles, instructional design methodologies, and blended learning strategies.
• Proficiency in core legal and productivity applications including:
  • iManage MS Office 365
  • Windows 11
  • Elite 3E Finance
  • Emburse Expenses
  • Kofax PDF
• Advanced knowledge of document management, template tools, PDF handling, and TOA/TOC generation.
• Familiarity with Learning Management Systems and eLearning tools.
• Experience with UKG Pro Learning is preferred.
• Strong written and verbal communication skills.
• Excellent presentation and organizational abilities.
• Ability to work independently and collaboratively.
• Ability to adapt and progress in a demanding environment.

Work Environment

• Hybrid position: Combination of remote and in-office work.
• Ability to work on site during standard business hours min of 3 days per week.
• Frequent use of computers, phones, and office equipment.
• Occasional travel to firm offices.
• Ability to lift and carry up to 20 lbs for equipment setup when necessary

What We Offer

• Starting Compensation Range $70,000 - $85,000 a year
• Benefits, following 30 days of employment
• Full-time, non-exempt position
• Hybrid work schedule (3 days in office, 2 days at home)
• Professional growth
• Supportive, team-focused environment

As an Equal Opportunity Employer, we support and encourage workforce diversity and do not discriminate based on race, color, religion, gender, national origin, sexual orientation, gender identity or expression, ancestry, citizenship, creed, marital status, veteran status, age, family caregiving responsibilities, genetic profile or predisposition, pregnancy, or disability in any aspect of employment.