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Digital Reporter Transcription Trainer

Remote
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Train, coach, and develop Digital Reporters in transcription skills and best practices. Deliver structured training, evaluate performance, and create effective learning materials. Requires demonstrated experience as a Digital Reporter or transcriptionist with strong teaching and communication abilities.

Key Highlights
Fully remote position with comprehensive benefits including 401(k) match and tuition reimbursement
Direct impact on Digital Reporter workforce quality and readiness through hands-on training and coaching
Opportunity to incorporate AI and technology into training and transcription workflows
Non-traditional L&D background welcome; subject-matter expertise in digital reporting is primary requirement
Key Responsibilities
Deliver structured transcription training for Digital Reporters through instructor-led and other appropriate training methods
Coach and support trainees throughout a rigorous training program, providing clear feedback and reinforcing quality expectations
Hold trainees accountable for meeting training requirements while encouraging persistence and continued development
Assess trainee performance and identify knowledge or skill gaps requiring additional coaching or instruction
Develop, organize, maintain, and improve transcription training materials, exercises, reference guides, and other learning resources
Review existing training content and identify opportunities to improve organization, clarity, consistency, and effectiveness
Document departmental procedures, training standards, and processes in Confluence and other appropriate systems
Partner with National Operations and Digital Reporter leadership to ensure training aligns with operational expectations and quality standards
Serve as a subject-matter expert on Digital Reporter transcription processes and related procedures
Identify opportunities to incorporate technology and artificial intelligence into training and transcription workflows
Stay current on changes affecting digital reporting, transcription practices, technology, and company operating procedures
Travel to Esquire locations as needed to support training and operational needs
Technical Skills Required
Transcription Digital Reporting Training and Instruction
Benefits & Perks
Medical, dental, and vision insurance
Short- and long-term disability insurance
Basic life insurance and supplemental insurance
401(k) plan with company match
80 hours annual vacation leave
10 paid holidays plus 2 floating holidays
5 paid sick days per year
Tuition reimbursement
Nice to Have
CET (Certified Electronic Transcriber) certification
Experience training, mentoring, coaching, or onboarding Digital Reporters or transcription professionals
Experience developing training materials, procedures, job aids, or other instructional content
Experience documenting policies and procedures in Confluence or a similar knowledge-management platform
Experience working with a Learning Management System (LMS)
Experience using AI tools within transcription, reporting, training, or related workflows
Experience in a legal services, court reporting, deposition, or related environment

Job Description

Are you an experienced Digital Reporter or transcription professional who enjoys teaching others? and help develop the next generation of digital reporting professionals. In this role, you will use your knowledge of digital reporting and transcription to train, coach, and hold learners accountable as they build the skills needed to produce accurate, high-quality transcripts.This role is ideal for someone who understands the realities of digital reporting and transcription and has a passion for helping others learn. You don't have to come from a traditional Learning & Development background. Why Choose Esquire?
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