Technical Trainer - Legal - Remote Boston, DC or Chicago

Title: Senior Technical Trainer - Legal/Law firm

Location: Washington, DC, Chicago, IL or Boston, MA (Remote – must reside near one of the offices (Chicago, DC or Boston) - In the office 10 Days a year. If you don't live in one of the three cities than this will not be an option.

Travel: ~10 days per year (primarily Washington, DC)

Salary: Base ~$110,000 + bonus (some flexibility based on experience)

Benefits: Health, Medical, Dental, Vision, 401(k), PTO, and additional firm benefits

Role Overview

We are seeking a Senior Technical Trainer to support attorneys and staff through high-impact technology training across a global professional services environment. This role is primarily remote, with a strong preference for candidates located near Washington, DC or another major firm office.

This position is high priority due to an upcoming retirement and will play a critical role in new-hire onboarding, continuing education, and technology adoption across the firm.

The ideal candidate has deep experience delivering technical training, preferably in a law firm or legal services environment, with heavy exposure to Microsoft 365 and Adobe-based workflows.

Key Responsibilities

• Deliver technology training to new hires and existing employees, including application usage, remote access tools, and communication systems
• Design, develop, and maintain training curricula, documentation, reference guides, and learning paths
• Facilitate training through instructor-led sessions, one-on-one coaching, webinars, micro-learning videos, and eLearning modules
• Assess current and future training needs; recommend priorities and improvements to training programs
• Evaluate effectiveness of training delivery and content; maintain records and reporting
• Create and maintain user documentation, FAQs, and online learning materials within the LMS
• Develop eLearning content using tools such as Articulate, Camtasia, Vyond, Movavi, or similar
• Support firm-wide technology initiatives by testing and recommending new tools and platforms
• Coordinate training schedules, registration, and materials across multiple offices
• Provide limited technical support and documentation in accordance with service level expectations
• Partner closely with IT leadership and stakeholders to align training with business needs

Required Qualifications

• 5+ years of technical training experience in a professional services or law firm environment
• Demonstrated experience training Microsoft Office / M365 and legal technology tools
• Strong instructional design, facilitation, and presentation skills
• Ability to translate complex technical concepts into clear, practical instruction
• Experience creating written curricula, user documentation, and eLearning content
• Comfortable presenting to both small and large groups, including senior professionals
• Strong client-service mindset with excellent written and verbal communication skills
• Willingness to travel occasionally to support in-person training sessions

Preferred Experience

• Prior law firm experience strongly preferred
• Familiarity with legal applications such as:
• Document Management Systems (iManage, Net Documents, or similar)
• Time entry and workflow tools
• Redlining and document comparison tools
• Experience supporting Adobe-heavy user environments

Education

• Bachelor’s degree in Computer Science, Information Systems, or a related field preferred
• Equivalent training and experience will be considered