Director of Billing

Director of Billing Summary We are a cellular services reseller serving business and consumer customers across the United States. We bill across multiple service lines and need someone who can personally own the billing operation from raw data through final invoice delivery. This is a hands-on operational leadership role. You will work directly in Excel every day, audit your own outputs, manage two billing specialists, and own every invoice that leaves the building. We are looking for someone who combines strong billing knowledge, people leadership, operational discipline, and relentless follow-through. You should be comfortable getting into the details yourself while also holding your team accountable. This role is best suited for someone who enjoys operating directly inside the billing process rather than managing from a distance. Location: Remote Hours: Full time, 9am to 5pm EST (full coverage required) Compensation: Base salary + 5% monthly bonus for billing accuracy, timeliness, and operational consistency What Success Looks Like Your primary measure is simple: invoices are issued accurately and on time according to each client's billing cycle date, accounts are actively managed, and billing issues are driven toward resolution quickly and consistently. Each client is billed monthly on their cycle date. You own that calendar. Follow-up on outstanding invoices, payment reconciliation, billing discrepancies, and unresolved issues must happen consistently on a predictable monthly rhythm. We need someone who does not wait to be reminded. If you are waiting on information from another person and they do not respond, you are expected to follow up, find another way to obtain the information, escalate when appropriate, and keep the issue moving. Consistent performance month after month earns your bonus and builds a long-term role here alongside a stable team. What You'll Own You will own the full billing cycle from raw usage and service data through invoice delivery, with accuracy and timeliness on every run. You will: Build SOPs and documentation for billing processes. Implement controls that catch errors before invoices are sent. Create processes that do not rely on memory or tribal knowledge. Directly manage a team of two billing specialists. Monitor deadlines, workloads, and completion of billing tasks. Step in quickly when deadlines slip, invoices are missed, or work is incomplete. Reconcile invoices against contracts, service records, usage data, and customer accounts. Track outstanding invoices through resolution. Follow up consistently on unresolved billing issues. Address billing discrepancies and customer disputes. Escalate problems when necessary and continue driving them toward resolution. Identify recurring problems and implement safeguards to prevent them from happening again. This is an operational ownership role. You are expected to know what is happening inside the billing operation and take responsibility for getting problems across the finish line. We Need Someone Who Takes Ownership The right person does not wait for someone else to tell them what to do when something goes wrong. If you discover a billing discrepancy, you investigate it. If an invoice is missing, you find out why. If another department has not provided information you need, you follow up. If someone does not respond, you follow up again or find another path. If your team makes a recurring mistake, you address the underlying process rather than simply correcting the individual error. We are looking for someone who is persistent, resourceful, organized, and results-driven without being unnecessarily aggressive or difficult to work with. You should be able to hold people accountable firmly and professionally while maintaining good working relationships and earning the respect of your team. AI and Resourcefulness We expect our team to use modern tools, including AI, to work more efficiently and solve problems. You do not need to be an AI expert, but you should be comfortable using tools such as ChatGPT, Microsoft Copilot, or similar systems to help you: Troubleshoot problems. Research unfamiliar issues. Analyze and organize data. Develop or improve Excel formulas. Identify potential discrepancies. Create and improve SOPs. Draft communications. Find ways to automate repetitive work. Develop potential solutions before escalating an issue. We value people who try to solve problems before asking someone else to solve them for them. AI is a resource. We expect you to use the resources available to you. What We Need From You Experience managing billing, accounts receivable, collections, revenue operations, or similar operational finance functions. Experience building or significantly improving billing controls, workflows, reconciliation processes, or reporting structures. Strong Excel fluency that you can demonstrate live, including: XLOOKUP VLOOKUP INDEX/MATCH SUMIFS Reconciliation across multiple sheets Cleaning and organizing messy raw data Building tracking and audit sheets You should be able to independently build, audit, and troubleshoot billing reports using incomplete or imperfect data. We are specifically looking for someone who: Follows up persistently until issues are resolved. Takes action without waiting for constant direction. Notices discrepancies quickly. Is comfortable addressing missed work and billing errors directly. Can manage small teams firmly and professionally. Builds respect without relying on intimidation. Takes ownership of outcomes rather than simply completing assigned tasks. Is resourceful when encountering problems. Uses available tools, including AI, to improve their ability to solve problems. Thinks in terms of controls, safeguards, accountability, and prevention. Can maintain consistent performance in a recurring monthly billing environment. Communicates clearly with management and other departments. Is looking for a long-term opportunity rather than a short-term position. Nice to Have Telecom or technology billing experience. Experience scaling billing operations. Collections and dispute resolution experience. Experience managing recurring billing environments. Experience managing customer accounts across multiple service lines. Exposure to automated billing systems alongside manual invoice processes. Experience implementing automation or AI-assisted workflows. How We Evaluate Candidates We evaluate applicants based on operational ownership, billing knowledge, attention to detail, Excel fluency, follow-through, communication, people management, resourcefulness, and ability to independently resolve problems. During the hiring process, you may be asked to demonstrate your Excel skills and walk through how you would handle real-world billing scenarios. We are particularly interested in how you think when something goes wrong. We don't just want to know what you did when everything went according to plan. We want to know what you do when someone doesn't respond, data is incomplete, an invoice is wrong, a deadline is approaching, or your team makes a mistake. How to Apply Send a short note answering all questions below. Applications without answers will not be reviewed. 1. List three Excel formulas you use regularly and explain how you have used them in a real work situation. 2. Describe a billing or collections process you improved. What specifically changed after your involvement? 3. Tell us about a time you had to repeatedly follow up on a billing issue, missed invoice, unpaid account, or another important business problem. What actions did you personally take, and how did you eventually get it resolved? 4. Describe a time you had to manage an underperforming employee or teammate. What did you do, and what was the outcome? 5. In your current or previous role, how did you ensure invoices were never missed or sent incorrectly? 6. Tell us about a problem you encountered at work where you did not immediately know how to solve it. How did you figure it out? 7. How have you used AI tools such as ChatGPT, Microsoft Copilot, or similar tools in your work? Give us one specific example. 8. Tell us about a role where you stayed for multiple years. What kept you there, and what are you looking for in your next long-term position?