Remote (North/Central/South America) | Full-time contractor | $2,200–$2,500 USD/month | Mon–Fri, 9am–5pm Pacific
The role
This is a billing job where you actually own something. You run our entire client billing cycle, and when you're not doing billing, you work directly with our VP of Operations.
Here's why it matters. Our clients are property managers, and the invoice we send them every month is the most regular contact they have with us. If it's accurate and on time, they trust us. If it's not, they don't. That's your responsibility.
And our billing is not simple. We charge per listing. Listings get added and removed constantly, and rates vary depending on the software each listing runs on, so invoice amounts change every single month. Someone has to watch every account, catch every change, set up the new rates, and get every invoice right. That someone is you. If you want billing where the numbers stay the same, this is the wrong job. If you like being the person who keeps a moving system accurate, keep reading.
Who we are
HostGenius is a community for property managers. Property management companies across Canada and the US join us to grow their businesses. We're a lean team and we move quickly.
What we care about
You'll be handling client money and an executive's priorities. We can teach you our systems. We can't teach character. So here's what we actually care about:
- Own the outcome. If you sent it, you checked it. If something breaks, you flag it and fix it. No "I thought someone else had that."
- Candid and transparent. Bad news travels fast here. If a number is wrong or a deadline is slipping, you say so before anyone has to ask.
- Always improving. The process should get better every month, and you're the one who makes it better.
If that sounds obvious to you, good. It isn't obvious to most people.
What you'll do
The short version: you own billing and AR. Everyone we're supposed to bill gets billed, and the money comes in on time. Here's what that looks like:
Billing (about 70% of your week):
- Run the monthly billing cycle for all clients in our internal billing system. Generate, check, and send every invoice on schedule.
- Set up new clients in the billing system: accounts, listings, and rates, correct from day one.
- Monitor every account for listing and rate changes, and update billing so invoices match reality every month.
- Make sure everyone we're supposed to bill gets billed. Nothing missed, nothing double-charged.
- Track payments and follow up on unpaid balances until they're paid.
- Answer client billing questions within one business day.
- Hand finished invoices to our bookkeeper for entry into QuickBooks.
- Reconcile the billing system against payments received at month end.
Once you've got the core down:
- Commission-based client billing (our edge cases).
- Damage waiver billing for revenue partners.
- Billing audits across our internal system and the software platforms we use.
Supporting the VP of Operations (about 30%):
- Chase down answers from clients, vendors, and teammates. Track follow-ups. Keep projects moving.
- Handle prep work: meeting notes, data pulls, research, first drafts of reports and SOPs.
- Use AI tools (ChatGPT, Claude) for drafting, summarizing, research, and data cleanup. This is a day-one expectation, not something we'll teach you.
To be clear about that 30%: this is not an inbox-and-errands assistant job. It's project work for the person who runs our operations. And billing always comes first. Those deadlines don't move.
Who this is for
- You want to own an area, not assist with one. You'd rather be accountable for a result than wait to be told what to do.
- You have 2+ years in billing, AR, or bookkeeping where you ran a recurring cycle yourself. Invoicing runs, client statements, month-end. Not just data entry inside someone else's process.
- You're comfortable with spreadsheets and basic math. Formulas, percentages, checking totals. Nothing fancy.
- You learn new software quickly. We'll train you on our billing system. QuickBooks or Xero experience helps but isn't required.
- You're already competent with AI tools like ChatGPT or Claude. You use them in your real work and can show us exactly how. If you'd need training on this, don't apply.
- You like variety. Invoices in the morning, a research task in the afternoon, nothing dropped.
- Your written and spoken English is strong. You'll write to clients and executives every day. Spanish is a plus.
- A $12 discrepancy bothers you until you find it.
- You can work 9am–5pm Pacific, Monday to Friday, with reliable internet.
Pay and setup
- $2,200–$2,500 USD per month, based on experience. Independent contractor, paid in USD.
- Fully remote. Long-term role with room to grow.
How to apply
Read this section carefully. Incomplete applications are not reviewed, and neither are applications that ignore the instructions.
- The basics. How many years you've spent running a recurring billing or invoicing cycle. The billing or accounting software you've used and for how long. Your monthly rate expectation in USD. Confirmation you can work 9am–5pm Pacific, Monday to Friday.
- Your track record. In 150 words or less: the billing cycle you personally ran. How many clients or invoices per month, on what software, what your exact role was, and one billing error you caught before it went out. Start your answer with the word BALANCED.
- One email. A client's invoice is 30 days overdue and they haven't replied to your first reminder. Write the follow-up email exactly as you'd send it. 150 words maximum.
- One AI example. Describe a real task you completed with an AI tool in the last month. Include the task, the tool, the exact prompt or approach you used, and what you did versus what the AI did. 150 words maximum.
- A Loom video, camera on. 60–90 seconds covering three things: who you are, the most complex billing process you've personally run — with the numbers (clients, invoices per month, dollar volume) — and why you want this role.
Everything you tell us here gets checked against your references later in the process.
We reply to every complete application. From there: a 15-minute screening call, a test project, reference calls, and a final interview. About two weeks total.