Accounting & Invoicing Specialist (Remote Contractor)

Company: Nest Marketing (DTC email & SMS retention marketing agency)
Type: Remote contractor Reports to: Founder / Operations

We're hiring an Accounting & Invoicing Specialist to own our monthly client invoicing and day to day financial record keeping. You'll turn the end of month numbers into accurate, on time invoices across our payment platforms, keep our books clean and reconciled, and support the team's payroll. This is a detail heavy, process driven role where accuracy and reliability matter more than speed.

What you'll do

• Draft monthly client invoices in Stripe and Square using the exact amounts from the end of month report

Route each invoice to the correct platform and currency: Stripe for USD clients, Square for CAD clients, converting USD to CAD accurately where needed

• Clear old or outstanding drafts before creating the new month's invoices
• Cross reference every invoice against the client tracker, only billing clients with valid invoice dates for the current cycle
• Hold all invoices on draft until they're reviewed and approved, then send once confirmed
• Reconcile transactions against bank statements so every description and amount is recorded correctly
• Identify and correctly handle voided transactions so they're excluded from totals and reporting stays accurate
• Maintain organized, up to date financial records and expense tracking
• Support team payroll through WISE, including setup for new hires
• Flag discrepancies, missing amounts, or anything unclear before invoices go out
• Give clear status updates and notify the team promptly once each batch of drafts is ready for review

Tools you'll use

• Stripe and Square for invoicing and payments
• WISE for payroll and international transfers
• Google Sheets and Google Docs for trackers and reports
• Slack for team communication

What we're looking for

• 2+ years in bookkeeping, accounting, accounts receivable/payable, or invoicing
• Hands on experience with Stripe and Square, or the ability to get up to speed quickly
• Comfortable working across multiple currencies (USD and CAD) with accurate conversions
• Strong spreadsheet skills and comfort working from structured trackers and reports
• Sharp attention to detail with a habit of double checking your own work
• Reliable and deadline driven, especially around month end close
• A clear written communicator who gives updates without being chased
• Able to follow a defined process closely, and asks before assuming
• Discreet and trustworthy with financial and client information

Nice to have

• Experience supporting an agency or a business with many active clients
• Familiarity with WISE or similar international payroll tools
• Bank reconciliation or statement review experience
• Experience running a recurring monthly close process

Working arrangement
Remote, contractor basis
Workload concentrates around the end of each month, with lighter ongoing bookkeeping through the month
Some overlap with EST hours for reviews and hand offs

Questions:
1. Walk us through your process for a typical month-end close — from receiving the end-of-month report to sending approved invoices. How do you catch errors before they reach a client, and what's your system for cross-referencing the client tracker against invoice dates?
2. Tell us about a time you found a discrepancy — a mismatched amount, a voided transaction that wasn't excluded, a currency conversion that looked off — during reconciliation. How did you spot it, and what did you do next?
3. This role runs on Stripe, Square, and WISE across USD and CAD. What's your hands-on experience with these specific tools (or similar multi-platform/multi-currency setups), and how comfortable are you managing payroll setup for new hires in WISE?

* HOW TO APPLY *

*You must include your Name + Accounting & Invoicing Specialist in the subject line of your application for it to be considered (this shows you actually read it and is very important; if you do not have it in there, your application will be skipped).

1.) Send us a message answering all 3 questions
2.) Include examples of your work

We look forward to hearing from you!