Specialist, Learning & Development

About The Role

The Specialist, Learning & Development is responsible for developing and delivering transcription training for Digital Reporters. The primary focus is helping trainees build proficiency in transcription, with the scope potentially expanding to include other Digital Reporter training and development needs. This is a hands-on role requiring subject-matter expertise, teaching, organization, accountability, and encouragement. The role is fully remote.

Key Responsibilities

• Deliver structured transcription training for Digital Reporters through instructor-led and other appropriate methods.
• Apply practical digital reporting and transcription experience to help trainees understand technical requirements and real-world application.
• Coach and support trainees, providing clear feedback and reinforcing expectations for quality and performance.
• Hold trainees accountable for meeting training requirements while encouraging persistence and continued development.
• Assess trainee performance and identify knowledge or skill gaps.
• Develop, organize, maintain, and improve transcription training materials, exercises, reference guides, and other learning resources.
• Review existing training content for opportunities to improve organization, clarity, consistency, and effectiveness.
• Create new training materials as business needs, technology, workflows, and Digital Reporter responsibilities evolve.
• 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 Esquire's operating procedures.
• Support additional Digital Reporter training initiatives.
• Participate in training-related projects, process improvements, and other assigned initiatives.
• Travel to Esquire locations as needed to support training and operational needs.

Requirements & Tech Stack

• Demonstrated experience as a Digital Reporter, court reporter, transcriptionist, or in a closely related role.
• Strong knowledge of transcription processes, terminology, quality expectations, and best practices.
• Demonstrated ability to teach, mentor, coach, or support the development of others.
• Strong written and verbal communication skills.
• Ability to evaluate work, provide constructive feedback, and clearly explain technical concepts.
• Strong attention to detail and commitment to accuracy.
• Ability to organize complex information and turn it into clear, usable training materials.
• Comfort working with technology and learning new tools and systems.
• Willingness to use and explore AI-enabled tools and technologies as they apply to transcription and training workflows.
• Ability to work independently while collaborating effectively with National Operations, leadership, and other stakeholders.
• Strong sense of accountability and follow-through.

Preferred Qualifications

• 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.

We Offer a Comprehensive Benefits Package Including

• Insurance: Medical, dental, vision, short- and long-term disability insurance, basic life insurance, and supplemental insurance for employees and their dependents.
• Retirement: Eligibility to enroll in the company’s 401(k) plan with match contribution.
• Paid Time Off: Two weeks of vacation leave per year (80 hours annually).
• Holidays: 10 paid holidays per year and 2 paid floating holidays per year.
• Sick Leave: 5 paid sick days per year.
• Tuition Reimbursement: Financial assistance to support career development.