Senior Executive Assistant and Operations assistant for MSP, IT Services (Remote, Philippines)

We're a US-based managed services provider serving healthcare, manufacturing, and compliance-focused companies. Five people on the team. We're looking for someone who can become the operational backbone of the company.

This is not just a virtual assistant role. We need someone with real experience in the IT services world who can manage executive communications, dispatch tickets, handle procurement, and take on special projects, all in the same day. You'll work directly with the owner and touch every part of the business.

The right person for this role is sharp, proactive, and versatile. You're someone who sees what needs to happen next and does it before anyone asks. You write emails that are warm, clear, and professional. You understand how an MSP runs well enough to triage a ticket, talk to a client about an invoice, and schedule a project kickoff without needing everything explained. You're curious about technology, interested in AI tools and automation, and energized by variety.


What you'll be doing

Managing the owner's calendar, inbox, and daily priorities. Drafting and sending client emails on his behalf. Providing briefings before meetings and tracking action items after.

Dispatching tickets. Triaging incoming requests, assigning to the right technician based on skill and availability, and sending professional client acknowledgments.

Procurement. Processing hardware and software orders, tracking shipments, managing vendor quotes, updating asset records.

Invoicing and billing support. Preparing monthly invoices, sending after approval, tracking receivables, flagging overdue accounts.

License and renewal tracking. Monthly reconciliation of client license counts against billing. Vendor renewal calendar maintained so nothing catches us by surprise.

vCIO engagement support. Tracking recommendations, action items, and follow-ups from strategic client meetings. Sending follow-up communications to clients. Flagging overdue items.

Client onboarding and offboarding admin. Non-technical onboarding tasks for new clients: welcome communications, documentation setup, credential coordination. Offboarding checklists when client employees leave.

Special projects as needed. Research, vendor comparisons, process documentation, internal reporting. The kind of work where we say "can you figure this out?" and you come back with something organized and useful.


What we're looking for

3+ years working in an MSP, IT services company, or technology-focused business. You understand multi-tenant environments, ticketing systems, and the pace of managed services.

Excellent written and spoken English. This is the most important requirement. You'll be writing to clients, drafting emails on behalf of the owner, and occasionally joining calls. Your communication needs to be clear, warm, and professional without sounding scripted or corporate.

Technical literacy. You won't be fixing anything, but you need to understand the landscape. You know the difference between a Microsoft 365 issue and a networking issue. You can read a ticket and route it to the right person. You understand what conditional access, Intune, and Entra ID are at a conceptual level.

Proactive and organized. You follow up before anyone has to ask. You flag things that are coming due. You anticipate what's needed next. If something falls through the cracks, it bothers you.

Comfortable with variety. Your day will include dispatch, client emails, procurement, calendar management, and special projects. That range should energize you, not overwhelm you.

Interest or experience in AI tools, scripting, or automation. You've used ChatGPT, Claude, or similar tools to make your work more efficient. Or you've built a simple script or automation to eliminate a repetitive task. We're an AI-forward team and we want someone who thinks this way.


What we offer

Full-time remote. $1,000 to $1,400/month depending on experience. Minimum 4 hours daily overlap with US Mountain Time. 60-day trial period so we can both make sure it's a good fit. A role with real variety and direct impact on how the company runs.


How to apply

To be considered for this role, please include ALL THREE of the following:

1. Your resume.

2. A short document (PDF or Word) responding to the following. This is how we'll evaluate your writing, formatting, and technical comprehension. Please take care with how you present it.

Writing exercise: Draft the emails you would send in each scenario.

Scenario A: A client emails asking why their monthly invoice is $300 higher than last month. The reason is they added 6 new employees mid-cycle and the prorated Microsoft 365 licensing was included. Draft the response you'd send on behalf of the company owner.

Scenario B: A client submits a support ticket that says ";email isn't working." You need to acknowledge the ticket and ask the right clarifying questions so the technician who picks it up can move quickly. Draft the response to the client.

Tech triage: For each of the following, tell us what category of issue it is and which type of technician you'd route it to (for example: identity/access specialist, endpoint tech, networking, general support).

- "Users in our Denver office can't connect to the VPN since this morning."
- "I can't get into my email on my phone but it works fine on my laptop."
- "We added a new employee and they need access to SharePoint, Teams, and our project management tool."
- "Our QuickBooks database is running really slow and it's hosted on a server in our office."

AI and automation: Describe a time you used AI tools, scripting, or automation to make a repetitive task more efficient. If you haven't yet, describe a task from your current or previous role that you think could be automated and how you'd approach it.

3. A short video (3 to 5 minutes) introducing yourself. Tell us about your MSP or IT services experience and what you'd bring to this role. Speak naturally. We're listening for communication clarity and how you think, not a rehearsed pitch.