About the role
NeedAWebNow is a sole proprietorship that bills monthly retainers from $297, one-time projects from $1,200, hosting plans, and a catalogue of individual services — plus affiliate and white-label partner commissions going the other way. That is a lot of small transactions for one person to also be the lead strategist on. As Bookkeeper and Billing Administrator you take the books off the founder’s desk and keep them in a state an accountant can close without a week of archaeology.
What you’ll do
- Keep the books current: categorise income and expenses, reconcile bank and Stripe activity, and chase down the transactions that do not match anything.
- Run client billing — issue invoices from the dashboard, apply the agreed discounts and credits, and follow up on what is past due, politely and on a schedule.
- Track recurring revenue properly: which retainers and hosting plans renewed, which failed, which were cancelled, and what that does to the month.
- Process affiliate and partner commission payouts against what actually converted, not against what was claimed.
- Produce a monthly close the founder can read in ten minutes: revenue, costs, receivables, and anything that looks wrong.
What we’re looking for
- Two or more years of real bookkeeping for small businesses, with references. US small-business bookkeeping specifically — this is a Florida sole proprietorship, not a corporate finance department.
- Fluency in at least one standard bookkeeping package and comfort reconciling against Stripe and bank exports.
- Discretion. You will see every client’s pricing, including the discounts that were given and the ones that were not.
- The nerve to tell the owner when a number is wrong, including when the number is his.
Schedule
Contract, part-time — roughly 8–15 hours a week, heavier at month-end. Hybrid: mostly remote, with on-site time at our Orlando office at Pipeline Workspaces, 20 North Orange Avenue, when paperwork needs to be handled in person. This is a contractor engagement, not an employee position.
About this posting
This is an open, evergreen posting. We keep it up whether or not there is a seat free this month, because the alternative — starting a search the week we need somebody — is how agencies end up hiring whoever is available instead of whoever is right. There is no deadline on it and no urgency to manufacture. If you are good at this, apply, and we will talk; if the fit is there and the work is not yet, we will tell you that honestly and keep your application on file.
Every application comes to us through this page. We do not post on Indeed or any other job board, and nobody at NeedAWebNow will ever ask you to pay for anything as part of applying.