Operations & Executive Assistant (Remote – Long-Term)

This is not a typical assistant role.

We are building a company where AI handles the routine work, and our people handle the thinking. If you are someone who already works that way — or wants to — this role was built for you.

We are looking for an Operations & Executive Assistant who is as comfortable setting up an AI workflow as they are managing a client invoice or reconciling a vendor bill. Someone who sees a repetitive task and immediately thinks "how do I automate this" rather than "I'll just do it manually every time."

If that is how your mind works, keep reading.

~~~~~~~~~~
~About Us~
We are a Canadian Managed IT Services company supporting 225 devices across 15 business clients. We are growing fast and hiring an Operations, Accounting & Executive Assistant to help remove bottlenecks so our founder can focus on scaling the business from 225 to 500+ endpoints.

The person in this role will not just help us operate — they will help us build systems that let us scale without adding headcount at every step.

~~~~~~~~~~
~Your Mission~
Keep our operations and customers organized, our accounting accurate, our clients well-billed, and our vendor invoices reconciled — while continuously finding smarter, AI-powered ways to get more done with less manual effort.

~~~~~~~~~~
~Work Schedule~
- Full-time, 40 hours per week
- Flexible schedule with a minimum 4-hour overlap with Pacific Time (Canada)
- You choose your remaining hours within reason

~~~~~~~~~~
~Compensation~
- CAD $600 – $1,200/month depending on experience
- Paid bi-weekly
- End-of-year performance bonus tied to company growth and your contribution to it — the more you help the business grow, the more you share in that success
- Long-term role with a clear path to increased responsibility and pay

~~~~~~~~~~
~Primary Responsibilities~

~Founder Support~
- Manage and organize email inbox
- Respond to simple client inquiries
- Schedule meetings and follow-ups
- Track action items and tasks
- Prepare weekly operations summaries

~Client Operations~
- Track client users, devices, and licenses for invoicing
- Maintain client records and documentation
- Assist with quoting clients, sourcing prices, Liason with founder and build quote, move quote to order and invoice appropriately and assist on collecting payment

~~~~~~~~~~
~Accounting & Billing — **Core Part of the Role**~
You will own the billing cycle end to end and be the first line of review on all financial activity. As we have about 15 customers this is important work, yet not the time spent task.
**2-4 years experience is required.**

~Invoicing & Billing~
- Review Microsoft 365 license counts via Ingram Micro before each billing cycle to ensure every license is accounted for and billed correctly to the right client
- Cross-reference Ingram Micro invoices for hardware and software purchases — confirm what was ordered, delivered, and billed to the client matches
- Prepare accurate client invoices in Wave Accounting
- Review invoice counts and amounts before invoices go out — catch errors before clients see them
- Send client statements and follow up on overdue invoices professionally

~Payments & Deposits~
- Process incoming electronic payments and match them to open client invoices in Wave Accounting
- When the owner deposits a cheque by bank scan, a photo of the cheque will be uploaded to SharePoint — you will be notified and are responsible for marking the deposit against the correct invoice in Wave
- Track all deposits and flag any discrepancies

~Credit Card & Expense Review~
- Regularly review company credit card statements
- Match charges to client accounts or internal cost categories
- Flag any unrecognized or suspicious charges as potential fraud
- Initiate disputes through the appropriate channel when required

~Accounting Inbox — ----------
- Monitor and manage the accounting inbox
- Respond to client billing questions and payment inquiries professionally
- Process vendor invoices received by email
- Confirm payment receipts and send acknowledgements
- Escalate anything requiring owner decision

~~~~~~~~~~
~Operations Monitoring~
- Monitor support tickets in our Kaseya software stack
- Flag unresolved issues
- Ensure documentation is kept up to date

~~~~~~~~~~
~Growth Support~
- Maintain prospect quotes and follow up
- Help organize proposals
- Help hire and work with Marketing Manager

~~~~~~~~~~
~AI & Automation — Central to This Role~
We do not expect you to do everything manually. We expect you to figure out what AI can do, set it up, manage the output, and escalate only what needs a human decision.

- Identify repetitive tasks and build AI workflows to handle them
- Manage and review AI-generated outputs before they reach clients or the founder
- Continuously look for ways to do more with less manual effort
- Help the company build systems that scale without adding headcount

The goal is not for you to work harder. It is for you to work smarter — and help the whole company do the same.

Over time, your role will shift from doing the work to managing the systems that do the work. That is the direction we are heading, and we want someone who is excited about that future — not threatened by it.

~~~~~~~~~~
~Required Skills~
- Excellent written and spoken English
- Bookkeeping or invoicing experience — you must be comfortable working with numbers and financial records
- Experience with AI tools and automation

~~~~~~~~~~
~Helpful Experience~
- Wave Accounting or similar bookkeeping software
- Microsoft 365 and SharePoint
- PSA or ticketing systems (e.g. Kaseya)
- Distributor or vendor invoice reconciliation
- AI tools (ChatGPT, Claude, or similar)

~~~~~~~~~~
~Tools We Use~
- Wave Accounting
- Ingram Micro distributor portal
- Kaseya software stack
- Microsoft 365 and SharePoint
- PSA / ticketing systems
- Spreadsheets and documentation tools
- AI tools — and we are always adding more

~~~~~~~~~~
~Personality We Are Looking For~
- Extremely organized
- Detail-focused — billing errors cost us money and client trust
- Proactive problem solver — you fix things before being asked
- Calm and dependable
- Trustworthy with financial information
- Genuinely excited about building better systems
- You see AI as a tool that makes you more powerful, not a threat to your job
- Reliable, consistent, and self-managed

~~~~~~~~~~
~Weekly Report You Will Own~
- Invoices sent
- Payments received and deposits processed
- Overdue invoices and follow-up status
- Credit card review status and any flagged charges
- Operational issues needing attention
- Priorities for the coming week

~~~~~~~~~~
~Long-Term Opportunity~
As AI takes over more of the routine work, this role grows with it. Your path could lead to:

- Operations Manager
- Finance Coordinator
- Automation & Process Manager

We are looking for someone who wants to grow with us for years, not months — and who wants to be part of building something, not just maintaining it.

~~~~~~~~~~
~How to Apply~
To be considered, your application must include all four of the following:

1. Your experience with operations, admin, or bookkeeping — be specific about what you did
2. The tools you have used — software, platforms, and AI tools
3. A specific example of how you have used AI to save time or improve a process
4. An example of a time you caught a billing or financial error before it became a problem

~Bonus Task — complete this to stand out:~
Review the following client billing summary:

Client A | 12 devices | 10 licenses billed | 12 on record | Oct 1 | Unpaid | 45 days overdue
Client B | 8 devices | 8 licenses billed | 8 on record | Oct 15 | Paid
Client C | 22 devices | 22 licenses billed | 25 on record | Sept 15 | Unpaid | 60 days overdue
Client D | 5 devices | 5 licenses billed | 5 on record | Oct 20 | Paid
Client E | 17 devices | 20 licenses billed | 17 on record | Oct 1 | Unpaid | 45 days overdue

Answer these three questions:

1. Which clients have a billing discrepancy and what is the issue with each?
2. Which clients need immediate payment follow-up and why?
3. How would you use an AI tool to automate the overdue invoice follow-up process so you are managing it rather than writing each email manually? Describe your approach in 2-3 sentences.

Applications that do not follow these instructions will not be considered.