Senior Billing Specialist

JOB DESCRIPTION

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.

Our 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:

• 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.

• You can stay calm, clear, and confident when a client questions whether a $20,000 balance is worth it, and explain the value without becoming defensive or immediately conceding.

• If you have ever been described as \"the person who can get anyone to pay\" and you know the reason is not because 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 own it. Investigate first, fix what’s within your authority, and escalate only what isn’t, with your findings and a recommended resolution attached.

• 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.

JOB RESPONSIBILITIES

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

• Before escalating any billing complaint, open the invoice, time entries, and matter notes and determine what happened. Every escalation email includes what you found and what you recommend.

• “Call your attorney” is never an acceptable first response to a billing question.
• 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.

• Respond to every credit request or billing dispute within one business day, and close the loop with the client in writing once it’s resolved. No client should have to ask twice.

• When attorneys communicate retainer reductions or billing pauses, document the

instruction in Clio at the matter level the same day.

QUALIFICATIONS

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.
• 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 ($55,000- $70,000) commensurate with experience.

TO APPLY:

If you believe it would be a perfect fit for you, you are invited to participate in a brief AI Interview using this link:

To continue the application process, send your resume with a cover letter telling us why you would be our perfect candidate. 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.

Applications that skip over the AI Interview, Cover Letter, or either question will not be reviewed.