Operations & Executive Assistant (Remote, Long-Term)

About the Role

This position is far from a conventional assistant role. It’s designed for a professional who embraces AI and automation to handle repetitive tasks efficiently while managing core operational, executive, and accounting responsibilities. You will be instrumental in building scalable systems that let the company grow without proportionally increasing workforce size.

Company Background

We are a Canadian Managed IT Services company supporting 225 devices across 15 business clients. As we accelerate growth towards 500+ endpoints, we seek a dedicated Operations, Accounting, and Executive Assistant to help eliminate bottlenecks and enable our founder to concentrate on expansion efforts.

Primary Responsibilities

• Provide executive support including managing the founder’s email inbox, responding to basic client queries, scheduling meetings, tracking tasks, and preparing weekly operational summaries.
• Maintain client operations by tracking users, devices, licenses for invoicing, managing client documentation, assisting with quotes, prices, and coordinating order-to-invoice-to-payment cycles.
• Take ownership of end-to-end billing processes, including verifying license counts and invoices, preparing accurate client invoices using Wave Accounting, monitoring payments, and following up professionally on overdue invoices.
• Process and reconcile payments, manage electronic deposits, and ensure accurate application of these against client invoices.
• Review and reconcile company credit card charges, identify any suspicious transactions, and coordinate dispute resolutions as necessary.
• Oversee the accounting inbox by handling billing inquiries, processing vendor invoices, confirming payments, and escalating significant issues to ownership.
• Monitor support tickets via Kaseya software, flag unresolved cases, and ensure up-to-date documentation.
• Support business growth efforts through maintaining quotes, organizing proposals, and collaborating with the Marketing Manager.
• Develop, implement, and manage AI-driven workflows to automate repetitive tasks, review automated outputs, and ensure only critical issues require human intervention.

Work Schedule

• Full-time commitment of 40 hours per week.
• Flexible working hours with a minimum of 4-hour overlap with Canadian Pacific Time.
• Ability to select remaining working hours within reason.

Compensation

• Monthly salary between CAD 600 and CAD 1,200 based on experience.
• Bi-weekly payments.
• Performance-based annual bonus linked to company growth and individual contribution.
• Long-term role with potential for increased compensation and responsibilities.

Required Qualifications and Skills

• Excellent verbal and written English communication skills.
• 2-4 years of experience in bookkeeping or invoicing; comfort with financial data.
• Familiarity and practical experience with AI tools and automation platforms.

Preferred Experience

• Proficiency with Wave Accounting or similar bookkeeping software.
• Experience with Microsoft 365 and SharePoint.
• Knowledge of PSA or ticketing systems such as Kaseya.
• Skills in distributor or vendor invoice reconciliation.
• Hands-on experience with AI platforms like ChatGPT, Claude, or equivalents.

Key Tools Utilized

• Wave Accounting
• Ingram Micro distributor portal
• Kaseya management software
• Microsoft 365 and SharePoint
• PSA/ticketing systems
• Documentation and spreadsheet tools
• Various AI technologies continuously added to improve processes

Ideal Personal Attributes

• Highly organized and detail-conscious, especially in billing accuracy.
• Proactive problem solver who addresses issues before they escalate.
• Calm, reliable, trustworthy with handling confidential financial information.
• Enthusiastic about creating and optimizing systems through AI and automation.
• Self-managed, consistent, and dependable team member.

Reporting Responsibilities

• Weekly reports on invoices issued, payments handled, overdue invoice follow-ups, credit card charge reviews, operational issues, and priorities for the upcoming week.

Long-Term Career Potential

• Progression paths include becoming an Operations Manager, Finance Coordinator, or Automation & Process Manager.

Application Instructions

Applicants must submit comprehensive details including:

• Specific past experience in operations, administration, or bookkeeping.
• List of software, platforms, and AI tools used.
• An example illustrating how AI helped save time or enhanced a business process.
• An incident where a billing or financial discrepancy was identified and resolved before becoming problematic.

Additionally, applicants are encouraged to complete a bonus task involving analyzing a client billing summary and answering related questions to demonstrate suitability.