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 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

• 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.

What Success Looks Like

Success in this role means Digital Reporters are better prepared, more confident, and consistently meeting the transcription standards required by Esquire.

You'll know you're succeeding when you:

• Deliver effective transcription training that prepares Digital Reporters for their roles.
• Help trainees understand expectations and develop the skills necessary to succeed.
• Identify performance gaps early and provide effective coaching and intervention.
• Maintain accurate, organized, and easy-to-use training materials.
• Improve and expand training resources as the Digital Reporter program evolves.
• Help establish consistent training processes and documented procedures.
• Partner effectively with National Operations and leadership.
• Embrace technology and AI as tools that can improve training and transcription workflows.
• Balance high standards and accountability with encouragement and persistence.
• Contribute to improved quality, readiness, and performance across the Digital Reporter team.

Work Environment

This role is fully remote. The position requires professionalism, confidentiality, organization, and the ability to manage multiple project priorities in a fast-paced setting.

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: Employees receive two weeks of vacation leave per year, or 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 your career development

The Ideal Candidate

You don't necessarily need to be a career L&D professional to be successful in this role.

You might be a great fit if you're an experienced Digital Reporter or transcription professional who people naturally turn to when they need help. You know the work, you understand what good looks like, you can explain it to others, and you have the patience and persistence to help someone get there.

If you're a strong communicator, organized, comfortable with technology, willing to embrace AI, and excited about developing others, we'd like to hear from you.

Equal Opportunity & Accommodations:

Esquire Deposition Solutions provides equal employment opportunities to all applicants and employees without regard to race, color, religion, creed, gender, gender identity or expression, age, national origin or ancestry, citizenship, disability, sexual orientation, marital status, pregnancy, veteran status, membership in the uniformed services, genetic information, or any other basis protected by applicable law.

Qualified applicants with criminal histories will be considered consistent with applicable laws, including the California Fair Chance Act and similar laws in other jurisdictions.

If you are a qualified individual with a disability or a disabled veteran and require support throughout the application or recruitment process, you have the right to request reasonable accommodation. Submit your request to talent.acquisition@esquiresolutions.com.