Bookkeeper – AP/AR & Billing Operations

The ideal candidate is an experienced Bookkeeper responsible for managing day-to-day Accounts Payable (AP) and Accounts Receivable (AR), invoicing, and reconciliation for a U.S.-based private security and protection company with multiple brands.

This role ensures billing activity is accurately captured, invoices are deployed on time, and outstanding payments are properly tracked. The ideal candidate is highly organised, detail-oriented, and confident working independently without needing constant supervision or hand-holding.

Key Responsibilities:

• Manage day-to-day Accounts Payable (AP) and Accounts Receivable (AR) activities.
• Review ClickUp activity to identify completed work and billing activity.
• Prepare and deploy accurate client invoices based on activity recorded in ClickUp.
• Monitor accounts receivable and maintain accurate invoice and payment records.
• Track outstanding invoices and follow up on aged receivables as required.
• Perform regular bank and account reconciliations, identifying and resolving discrepancies.
• Review billing information across multiple brands and ensure transactions are correctly recorded.
• Maintain accurate and up-to-date bookkeeping records.
• Identify invoicing, reconciliation, or data discrepancies and proactively resolve them.
• Collaborate with relevant team members to clarify billing information where required.
• Help maintain consistent and reliable finance processes as the business continues to grow.
• Provide visibility to the CEO on outstanding invoices, discrepancies, and other relevant bookkeeping matters.

Requirements

Required Skills and Qualifications:

• Proven experience as a Bookkeeper, ideally with hands-on AP, AR, invoicing, and reconciliation experience (3+ years).
• Strong attention to detail and a high level of accuracy.
• Experience managing invoicing and accounts receivable/aging.
• Comfortable reviewing operational or project-management data and translating it into accurate billing.
• Strong problem-solving skills and the ability to identify errors before they become issues.
• Highly organised and able to manage multiple priorities independently.
• Self-directed and proactive — able to take ownership of responsibilities without needing constant guidance.
• Strong communication skills and confidence in raising discrepancies or asking the right questions.
• Comfortable working across different software platforms and learning new systems quickly.
• Experience working with remote teams is an advantage.

Systems & Tools

The business currently works across:

• ClickUp – program management and primary source for billing activity
• Notion – internal source of truth and documentation
• Asana – media and content scheduling
• DocuSign
• Upwork

Experience with ClickUp is an advantage, but strong systems aptitude and the ability to quickly understand a new workflow are equally important.

What Success Looks Like

In this role, success means having a reliable and accurate billing process where:

• Invoices are issued accurately and on time.
• ClickUp activity is consistently reviewed and reflected in billing.
• Reconciliations are completed accurately and discrepancies are addressed promptly.
• Outstanding invoices and aging are actively monitored.
• The CEO can trust that the books and billing activity are being properly managed.
• Finance tasks are handled proactively without requiring day-to-day supervision.