Specialist, Learning & Development

Are you an experienced Digital Reporter or transcription professional who enjoys teaching others?

Join Esquire as a Digital Reporter Transcription Trainer 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. We are looking for a strong digital reporting or transcription professional who can teach, communicate clearly, create effective training materials, and help trainees persist through a rigorous training program.

Why Choose Esquire?

Esquire is a leader in legal support services, known for our innovation, professionalism, accountability, and commitment to getting it right. Our Digital Reporters play an important role in delivering accurate, reliable services to our clients.

As a Digital Reporter Transcription Trainer, you will have a direct impact on the quality and readiness of our Digital Reporter workforce. You'll work closely with National Operations and other partners to ensure trainees receive the knowledge, practice, feedback, and support they need to succeed.

About the Role The Specialist, Learning & Development is responsible for developing and delivering transcription training for Digital Reporters. The primary focus of the role is helping trainees build proficiency in transcription, while the scope may expand to include other Digital Reporter training and development needs.

You will facilitate training, coach learners through challenging material, evaluate performance, identify opportunities for improvement, and maintain organized training resources. You'll also help strengthen and document training processes, procedures, and standards as Esquire continues to evolve its Digital Reporter program.

This is a hands-on role for someone who can balance subject-matter expertise, teaching, organization, accountability, and encouragement.

Key Responsibilities Deliver structured transcription training for Digital Reporters through instructor-led and other appropriate training methods.

Apply practical digital reporting and transcription experience to help trainees understand both the technical requirements and real-world application of the work.

Coach and support trainees throughout a rigorous training program, 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 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.

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 where appropriate.

Stay current on changes affecting digital reporting, transcription practices, technology, and Esquire's operating procedures.

Support additional Digital Reporter training initiatives as the needs of the business evolve.

Participate in training-related projects, process improvements, and other initiatives as assigned.

Travel to Esquire locations as needed to support training and operational needs.

What You'll Need Required 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…