Billing Operations Lead (Project Lifecycle Tracking Accounting/Reconciliation/Bookkeeping)

-- About the Business --

Our business coordinates service requests for commercial clients, connecting them with qualified vendors for maintenance, repair, cleaning, and other trade-related work.

After the work is completed, our department organizes the vendors’ reports, reviews the details for accuracy, and prepares clear client-ready reports and invoices. Our goal is to make sure every job is tracked properly from request through completion, documentation, billing, and payment.

-- The Opportunity --

Our department is growing fast, and we're looking for a Billing Operations Lead to work directly with leadership — overseeing, running, and improving our billing system.

Big picture: While the foundational systems are already built, we're continuing to upgrade and refine the system right under our feet. Because we are managing a high volume of moving parts while also improving the larger workflow, we need a steady, organized anchor - you - who can help keep operations moving with accuracy, consistency, and care.

You will track incoming jobs through their full lifecycle (from AP to AR), delegate clear step-by-step tasks by updating SOPs and using ClickUp for project management, escalate harder questions to management, and overall keep the machine running smoothly with reminders, follow-ups, and creative solutions to any and every challenge.

The person who thrives here takes pride in maintaining an accurate, complete, clean, well-run system, enjoys creating order out of chaos, loves seeing a project through from beginning to end, and holds themselves to a high personal standard.

As the business scales, there is real opportunity to grow with it and shape your own role.

-- Job Description --

We're looking for a sharp, detail-oriented professional to run our company billing lifecycle — and to care about it like it's their own.

This is not a role where you'll be handed a finished manual. Our systems are live and still evolving, and they'll keep changing as we grow.

We need a self-starting problem-solver who can keep daily progress steady while adapting smoothly to new steps and new tools — someone who reads an unclear situation, uses good judgment, and figures out the next right move — someone who operates independently but also knows when to reach out for guidance and clarity.

You will not be expected to fix everything alone. You will have leadership support, existing tools, and assistant help, but we are looking for someone who can steadily take ownership of the process.


-- This Role Is PERFECT For You If: --

* You have an analytical mind and love putting together puzzles and creating order out of chaos
* You have high personal standards
* You take deep pride in a clean, accurate, complete, well-running system
* You love the whole picture. There's a real satisfaction for you in tracking a job from a simple request all the way to a finalized, paid invoice — and you don't fully relax until the loop is closed.
* You take pride in your work — and being part of a team. You want to see the system run beautifully regardless of credit. You are a natural two-way leader, meaning you can give direction to assistants, while hearing their input, and bring solutions and suggestions to leadership, while taking direction from them as well.
* You start your own engine. You don't need a manager checking in on every step. You look at what needs doing, and you go. But you also know when to slow down and ask for guidance and clarity, with your own suggestions at hand.
* You're calm in ambiguity. When something isn't mapped out, you don't freeze — you use logic, context, and judgment to find the next best step, then flag it so we can document it.
* You're built for consistency. You've got the focus and stamina to hold a high standard day after day, not just in bursts.
* You enjoy being part of a growing business where the role and responsibility can expand over time.
* You have a natural curiosity about how field-service work gets done and either know or can quickly pick up the vocabulary of mechanical, electrical, repair, or cleaning work, enough to catch a billing error before it reaches a client.

-- Please Do NOT Apply If: --

- You need a finished manual or daily supervision to know what to do next.
- You'd rather move fast and cut corners than protect accuracy and data integrity.
- Routine bores you and you prefer to work in sprints.
- It stresses you out when systems and workflows are being actively built, changed and improved around you.

-- Compensation & Logistics --

$1,200 USD/month to start, full-time. *If you're the right fit, I'm genuinely open to hearing what feels right, good, and fair to you. I believe in open communication and all parties feeling comfortable bringing up their preferences and expectations.*

A 90-day review with real room to grow — in both pay and responsibility — as you take on more ownership.

A discretionary year-end bonus. I prefer steady, dependable pay over short-term incentives, so you can focus on doing great work.

Independent contractor role (no benefits).

Mostly independent schedule. I'm in the US Eastern time zone. A couple of hours of overlap (your evening) is helpful while you're getting up to speed and for occasional real-time questions — but it's a preference, not a hard requirement.

-- To Apply --

Please send me a short, genuine message answering these:

1. Tell me about a time you stepped into a role where the existing processes were unorganized or nonexistent. What was the high-level goal you were given, how did you figure out the underlying issues on your own, and what system did you build to keep things running smoothly every day?

2. What's your experience with billing, invoicing, job or work-order tracking, or coordinating other people's work?

3. How do you keep your own work accurate and moving when there are a lot of tasks and details to track at once?

4. What was your reason for leaving your most recent position? Are you currently employed and, if so, why are you looking to work with us?


Please also include:

1. Your resume, with the file named: LastName_FirstName - BillingLead.pdf

2. A url link to your result of this 10-15 minute work-personality assessment: ---------- (you *do not* need to provide your email / details when it suggests) and begin your subject for this whole message / application with the two top letters in order of highest percentage first (e.g., DC), followed by your info in this format: [ - Billing Operations - LastName_FirstName].

3. Your availability/hours (preferred and any flexibility you have) and when you would be available to start.

4. Any tools you've used — Google Sheets, Excel, ClickUp, CRMs, invoicing or job-tracking systems.

5. Anything else you'd like me to know and consider.

Shortlisted candidates will be invited to a short paid trial task.