Training Support Specialist - Information Technology - Dallas

Winstead is a leading Texas-based law firm with national practices serving clients across the country. We focus on exceeding our clients’ expectations by providing innovative solutions to their business and legal opportunities and challenges. We work as a trusted counsel to public and private companies, governments, individuals, universities, and public institutions.

Our business, transactions, and litigation practices serve key industries, including real estate, financial services, investment management and private funds, higher education and P3, airlines, healthcare and life sciences, sports business, and wealth management.

Position Summary

The Trainer is responsible for delivering and measuring high-quality technology training to firm staff and attorneys. This role focuses on hands-on instruction, developing clear and effective training materials, and supporting firm-wide technology adoption. The Trainer will conduct live training sessions, webinars, and new hire onboarding, while increasing the adoption of firm technology and processes, improving onboarding speed to competency, measuring training effectiveness, and recommending improvements.

Additionally, the Trainer will partner with attorneys on special projects, providing direct support for attorney-led initiatives and contributing to project outcomes. They will also serve as the team’s technology horizon-scanner—proactively researching emerging legal technology trends, anticipating what’s coming, and developing forward-looking training materials that prepare the firm before new tools and processes arrive.

This position will create and maintain written and video documentation to support ongoing learning and works closely with the Training Coordinator and other trainers to ensure consistent, engaging, and practical training experiences that align with firm needs.

Key Responsibilities

Training Delivery

• Conduct virtual and in-person training sessions for staff, attorneys, and new hires.
• Facilitate live webinars and workshops focused on firm technology and workflows.
• Provide one-on-one or small-group training as needed to reinforce learning.
• Adjust training delivery style and pace to meet the needs of different learner audiences.

Content Development and Documentation

• Create and maintain training documentation, including user guides, quick-reference materials, and job aids.
• Develop and update instructional videos and recorded training sessions.
• Ensure training materials are accurate, current, and aligned with firm standards and technology changes.
• Collaborate with subject matter experts to translate technical concepts into user-friendly content.

Technology Innovation and Forward Planning

• Proactively monitor emerging legal technology trends, tools, and industry developments.
• Anticipate upcoming technology changes affecting the firm and develop preparatory training content in advance.
• Research and evaluate new platforms, AI tools, and workflow innovations relevant to legal practice.
• Translate technology forecasts into actionable training roadmaps, keeping the firm ahead of the curve.
• Present findings and recommendations to firm leadership on technology-driven training opportunities.

Attorney and Special Projects Support

• Collaborate directly with attorneys on special projects requiring technology guidance, research, or training support.
• Assist attorneys in identifying and leveraging technology tools to improve workflow efficiency and case management.
• Develop customized training or reference materials tailored to specific practice group or project needs.
• Serve as a trusted resource for attorneys exploring new technology applications within their practice.
• Coordinate with firm leadership and practice group heads to align training priorities with active initiatives.

Learning Management System (LMS) Support

• Track training attendance and completion within the LMS.
• Upload, update, and maintain training courses and materials in the LMS.
• Assist with reporting on training participation and completion as needed.

Collaboration and Support

• Work collaboratively with other trainers to maintain consistent training quality and messaging.
• Participate in planning discussions for new software rollouts and technology changes.
• Provide feedback on training effectiveness and suggest improvements to content or delivery methods.
• Support firm initiatives by adapting training materials to evolving business and technology needs.

Qualifications

• 2–4+ years of experience in a training, instructional, or education-focused role, preferably within a legal or professional services environment.
• Demonstrated experience delivering virtual and live training sessions.
• Strong written communication skills with experience creating training documentation and instructional materials.
• Comfortable creating and presenting training to a wide range of technical skill levels.
• Strong organizational skills and ability to manage multiple training assignments simultaneously.
• High level of technical aptitude with the ability to quickly learn new applications and systems.
• Creative thinker with the ability to anticipate organizational needs and develop proactive solutions.
• Excellent interpersonal skills and a collaborative, service-oriented approach.

Preferred Skills

• Experience with legal technology platforms (e.g., document management systems, Microsoft 365, legal applications).
• Understanding of adult learning principles and effective training techniques.
• Experience creating or editing training videos (e.g., Filmora, Adobe Captivate, or similar tools).
• Familiarity with LMS platforms and basic training metrics.
• Experience working alongside attorneys or within a legal team on project-based work.
• Demonstrated ability to research and evaluate emerging technology tools and translate findings into training strategy.
• Familiarity with AI-powered legal tools and the evolving legal technology landscape.

Work Environment

This position operates in a professional office environment and may require occasional flexible hours and travel to accommodate training schedules and firm needs.

Winstead is an Equal Opportunity Employer. Employment decisions are made without regard to protected characteristics under applicable federal, state, or local law. The firm is committed to recruiting, hiring, developing, and retaining talented attorneys and professional staff in an inclusive and supportive workplace.