[Hiring] Legal Billing Assistant @Divorce with a Plan

Role Description

Divorce With A Plan is a Maryland family law firm committed to guiding clients through complex legal matters with clarity and professionalism. We are seeking a detail-oriented and client-focused Legal Billing Assistant to support our billing and collections operations. This role is integral to the firm's financial health and directly impacts the client experience. The ideal candidate brings hands-on experience in legal billing, particularly in family law, and is comfortable managing trust accounts, communicating with clients about balances, and partnering with attorneys to ensure accurate, timely billing.

Key Responsibilities

• Trust & Retainer Management
  • Monitor client trust balances daily and flag accounts that fall below the minimum retainer threshold.
  • Send timely replenishment requests to clients and follow up to ensure funds are received before work continues.
  • Apply trust funds correctly in Clio and ensure IOLTA compliance at all times.
  • Maintain accurate records of all trust transactions and payment activity.
• Billing & Invoicing
  • Review and audit attorney and paralegal time entries for accuracy, clarity, and completeness before billing.
  • Generate pre-bills, final invoices, and monthly review letters in Clio.
  • Ensure all billing descriptions clearly communicate the value of work performed to the client.
  • Manage work-in-progress (WIP) and coordinate with attorneys on billing cycles.
  • Run billing reports and provide regular summaries to the Controller and Office Manager.
• Collections & AR Management
  • Follow up on past-due balances in a professional and non-confrontational manner.
  • Set up and monitor client payment plans; escalate accounts that are not progressing.
  • Partner with attorneys on client calls when billing-related issues require legal explanation.
  • Initiate disengagement processes when appropriate and directed.
  • Maintain accurate accounts receivable records and prepare write-off requests for management approval.
• Client Communication
  • Handle a minimum of 10 client calls daily (collections + billing inquiries + new client billing setup).
  • Communicate clearly regarding balances, statements, and payment options.
  • Respond promptly and professionally, de-escalating concerns when needed.
  • Ensure alignment with the legal team on all billing communications.
• System & Process Support
  • Maintain and update client billing records in Clio.
  • Assist in identifying and implementing process improvements to billing workflows.
  • Support onboarding of new clients by setting up billing profiles and retainer agreements in the system.

Qualifications

• Minimum 2 years of legal billing experience, preferably in family law or a similarly complex practice area.
• Strong understanding of IOLTA trust accounting rules and compliance requirements.
• Experience with Clio or comparable legal practice management software.
• Proficiency in managing WIP, invoicing, trust fund applications, and billing reports.
• Excellent attention to detail with a strong track record of accuracy in billing and financial records.
• Professional written and verbal communication skills, especially in client-facing situations.
• Ability to handle sensitive billing conversations with discretion and composure.
• Highly organized with the ability to manage multiple matters and deadlines simultaneously.

Preferred

• Bilingual in English and Spanish — strongly preferred to support our diverse client base.
• Experience with collections and payment plan management in a legal setting.
• Familiarity with Maryland family law billing practices, retainer structures, and court fee schedules.
• Comfort working in a remote environment and collaborating with attorneys and staff across time zones.