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Please read this job description in its entirety before submitting your application. This position is not a billing specialist in the traditional sense. This role is results-driven and sits at the intersection of financial coaching and client advocacy.
Most billing specialist job posts describe someone who processes invoices, chases payments, and manages a spreadsheet. This is not that role.
At Divorce With A Plan, the Billing Specialist is the person who walks beside the client through the financial side of the hardest experience of their life. You are their guide. You are the one who helps them understand where their money is going, why it matters, and how every dollar they invest connects to the outcome they are trying to reach for themselves and their family. You are part of their walk, connecting their payment to their goals.
Clients are professionals and higher-net-worth individuals going through divorce across the state of Maryland. They are smart, capable people who are making financial decisions under stress they have never experienced before. They did not go to school for this. They have never hired a law firm. They do not know what an evergreen retainer is, what a trust replenishment request means, or why their invoice looks the way it does. And nobody in their life is going to explain it to them with patience, clarity, and genuine care unless you do
That is the job. Not collecting money. Teaching people how to use our service, showing them the value of what their legal team is doing, and making the financial side of their case feel manageable instead of terrifying. When you do that well, collections happen naturally. Clients who feel informed and cared for pay. Clients who feel ambushed and confused do not.
Here is who thrives in this role:
You are someone who genuinely likes people and is energized (not drained) by 20+ phone conversations a day. You remember details about people's lives because you actually care, not because you wrote it in a CRM.
You are the person your friends call when they need someone to listen, and also the person who will tell them the truth when they need to hear it.
You have high empathy, but you are not a pushover. You can hold a warm, caring conversation with a client who is crying on a Tuesday and follow it up with a firm, clear conversation about a past-due balance on a Wednesday, and both conversations feel authentic because they are.
You are organized without being rigid. You can manage 100 to 150 active client relationships simultaneously because you have a system, whether that is a color-coded calendar, a handwritten checklist, or a spreadsheet you built yourself.
You do not wait to be told what needs to happen. You check the attorney's calendar, you see a mediation in two weeks, and you pick up the phone before anyone asks you to.
If you have ever been described as "the person who can get anyone to pay" and you know the reason is not that you are pushy but because people trust you, this is your role
Here is who this role is not for:
This is not a data entry job. If you want to process invoices in the back office and never talk to a client, you will not be happy here.
This is not a role for someone who avoids difficult conversations. You will talk to people about money during the worst period of their lives. Some of those conversations will be uncomfortable.
You need to be able to sit in that discomfort with them and still move the conversation forward.
This is not a role for someone who needs constant direction. You will have structure (daily call blocks, weekly deliverables, escalation protocols), but within that structure, you are expected to think, prioritize, and act. If you see a problem, you fix it or flag it. You do not wait for a meeting.
This is not a collections role where you read from a script and move to the next number. Every call requires context. You will know what is happening on the client's case before you pick up the phone, and you will lead with that knowledge, not with the balance due.
$50,000 - $65,000
Be the Client's Financial Guide from Day One
Within five (5) business days of a new client retaining the firm, deliver a billing tutorial covering retainer structure, evergreen replenishment, invoice format, and what to expect at each stage of their case.
Conduct a live introductory call to walk through the material, answer questions, and establish the relationship before any billing activity begins.
Provide specific dollar ranges for upcoming cost events (hearings: $5,000-$10,000, mediations, trials: $15,000-$30,000) so the client is never surprised.
Introduce yourself as a non-billable point of contact the client can reach at any time for billing questions. You are free. Use that.
Keep Trust Accounts Funded and Clients Informed.
Monitor trust balances daily across 100-150 active client matters.
Call every client before sending a replenishment request. No replenishment email goes out without a phone call attempt.
When requesting additional retainers for upcoming events, reference the specific event by name and the date you first discussed it during the onboarding call. Clients remember when you remember.
Flag any matter below the trust threshold to the assigned attorney the same day. Not at the next billing cycle. The same day.
Collect with Context, Not Pressure.
Maintain accounts receivable below 2% of total billings.
Execute 12-15 outbound calls per day during the morning AR block, with every call documented in Clio.
Lead every collections conversation with a brief case update: what was accomplished, what is upcoming, how the work moves the client closer to their goal. Then address the balance.
When a client says they cannot pay, walk through every available option: credit cards, personal loans, family support, employer assistance, legal fee financing programs. Explore before you accept.
Send payment links same-day following any replenishment commitment.
Track and Escalate Billing Complaints
Log every billing complaint in the tracker with a documented timestamp and route it to the responsible attorney via email. No verbal-only escalations. Email creates the paper trail.
Produce a weekly deliverable every Friday: complaints resolved this week and complaints still awaiting attorney response.
Escalate any complaint involving bar grievance language, fraud allegations, or legal action threats to firm leadership the same day, regardless of dollar amount.
Coordinate with Attorneys Proactively.
Check attorney calendars for upcoming hearings, mediations, and trials. Initiate additional retainer requests before anyone asks you to.
Confirm all credits, write-offs, and billing holds in writing before any related bill is finalized.
If a credit exists and you are not sure it has been applied, hold the bill.
When attorneys communicate retainer reductions or billing pauses, document the instruction in Clio at the matter level the same day.
Required
2+ years in billing, collections, or accounts receivable in a professional services environment. Law firm experience strongly preferred.
High comfort with outbound phone calls and client-facing conversations. This role requires 20+ calls per day. If you do not like being on the phone, this is not the right fit.
Proficiency with practice management software (Clio Manage preferred, or demonstrated ability to learn within 30 days).
Ability to read and interpret legal invoices, time entries, trust account statements, and engagement agreements.
Strong written communication for documented escalations, client correspondence, and weekly deliverables.
Proficiency with Google Workspace (Gmail, Sheets, Calendar, Drive).
Demonstrated ability to manage 100+ active relationships simultaneously without dropping threads.
Preferred
Experience in a family law firm or litigation-focused practice.
Familiarity with Maryland Rules of Professional Conduct as they relate to billing. Training provided, but baseline awareness accelerates onboarding.
Experience with evergreen retainer models and trust accounting.
Prior use of LawPay, Dialpad, or Clio Grow.
Bilingual (English/Spanish) is a plus.
BENEFITS/WHY WORK HERE
Fully remote position. We serve clients across the entire state of Maryland. You work from wherever you work best.
Direct, measurable impact on firm revenue and client satisfaction. Your work is visible, valued, and tied to outcomes you can point to.
Structured daily workflow with defined call blocks so you always know what your day looks like.
Training on Maryland Rules of Professional Conduct as they apply to billing, giving you compliance knowledge that transfers to any law firm career.
A firm that builds systems, not workarounds. You will have scripts, checklists, escalation protocols, and technology supporting you from day one.
Competitive salary ($50,000- $65,000) commensurate with experience.
TO APPLY:
After reading the full job description, if you believe it would be a perfect fit for you, you are invited to participate in a brief AI Interview using this link: https://portal.divorcewithaplan.com/interview/legal-billing-assistant
We also ask that you send us your resume with a cover letter telling us why you would be our perfect candidate. Please tell us about:
A client relationship you built that directly led to a payment you might not have collected otherwise. What did you do differently than just asking for money?
How do you stay organized when managing 100+ accounts at the same time?
Walk us through your system.
Thank you!
Divorce With A Plan Hiring Team
Divorce With A Plan is a growing Maryland family law firm focused on helping clients navigate divorce and child custody matters with clarity, compassion, and confidence.
We serve professionals and families facing complex family law matters and believe that excellent legal representation requires more than knowing the law. It requires preparation, organization, strategic thinking, responsiveness, and a commitment to the client experience.
When you know your options, you reclaim your power.