Senior Training Specialist

Frontline Managed Services; Chicago (IL); On-site; USD 70,000 - 90,000; Full time

Job summary

Frontline Managed Services is looking for a Senior Training Specialist (Accounts Receivable Trainer) in Chicago, Illinois. This role is essential for designing and delivering training programs aimed at enhancing the skills of Accounts Receivable Specialists. Key qualifications include significant experience with legal billing systems such as Aderant and Elite 3E, along with strong training and facilitation skills. Success is measured by new hires being production-ready, improved collections performance, and high-quality training programs that align with business growth.

Qualifications

• 3+ years of experience in law firm billing or collections.
• 2+ years of experience in training, coaching, or facilitation.
• Strong understanding of accounts receivable processes.

Responsibilities

• Design and deliver onboarding and training programs.
• Conduct instructor-led and virtual training sessions.
• Coach employees on professional communication with attorneys.

Skills

Legal billing systems expertise

Training and facilitation

Communication skills

Accounts receivable processes

Advanced Excel proficiency

Education

Bachelor’s degree in Accounting, Finance, or Business

Tools

Aderant

Elite 3E

Job description

Frontline Managed Services® is a leading global outsourcing provider to the legal industry, supporting more than 600 law firms worldwide. Our Managed Financial Operations (MFO) team partners closely with attorneys and clients to improve financial performance through billing, collections, and accounts receivable management.

Position Summary

The Senior Training Specialist (Accounts Receivable Trainer) is responsible for designing and delivering training programs for Accounts Receivable Specialists supporting law firm clients. This role requires strong experience in law firm billing and collections, along with hands‑on expertise using legal billing systems such as Aderant, Elite 3E, or similar platforms.

The trainer will ensure employees are production‑ready, confident in managing attorney portfolios, skilled in collections best practices, and effective in professional communication with attorneys and clients.

Key Responsibilities

Training Delivery and Facilitation

• Design and deliver onboarding and ongoing training programs for Accounts Receivable Specialists
• Conduct instructor‑led and virtual training sessions
• Train teams on collections strategies, portfolio management, and law firm billing processes

Curriculum and Training Materials

• Develop and maintain SOPs, playbooks, job aids, and assessments
• Create training content covering the full accounts receivable lifecycle
• Include aging analysis, cash flow optimization, client terms, and reconciliation practices
• Ensure training programs are consistent, scalable, and up to date

Familiar with Instructional Design Tools

Legal Billing Systems Training

• Train employees on legal billing systems such as Aderant, Elite 3E, and similar platforms
• Teach workflows including aging review, collections tracking, and reporting
• Partner with Operations and IT to stay current on system updates and client configurations
• Incorporate changes into training content and materials

Coaching and Performance Support

• Coach employees on professional communication with attorneys and clients
• Train teams to manage sensitive collections conversations while preserving relationships
• Lead role‑playing exercises and real‑world case studies
• Assess trainee readiness through evaluations and simulations
• Provide ongoing feedback based on quality, productivity, and performance metrics

Collaboration and Continuous Improvement

• Partner with Operations leaders to identify performance gaps
• Implement targeted training solutions to address skill gaps
• Collaborate with Talent Acquisition to support hiring readiness
• Work closely with People & Culture and Learning & Development teams
• Track and report on training effectiveness, ramp time, and performance trends

Qualifications

• Bachelor’s degree in Accounting, Finance, Business, or related field (preferred)
• 3+ years of experience in law firm billing, accounts receivable, or collections (preferred)
• Hands‑on experience with Aderant, Elite 3E, or similar legal billing systems (Strongly preferred)
• 2+ years of experience in training, coaching, or facilitation
• Understanding of accounts receivable processes and law firm billing structures
• Advanced proficiency in Microsoft Excel and reporting tools
• Excellent communication and presentation skills
• Ability to simplify complex concepts for diverse audiences

What Success Looks Like

• New hires are production‑ready within expected timelines
• Improved collections performance and reduced outstanding AR balances
• Consistent, high‑quality training programs that scale with business growth
• Strong professionalism and confidence in attorney and client interactions
• Continuous improvement in quality, productivity, and team performance