Senior Executive Assistant / Client Operations - US IT Services Firm (MSP experience preferred)

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TYPE OF WORK

Full Time

SALARY

1400--1850

HOURS PER WEEK

40

DATE UPDATED

Jul 4, 2026

JOB OVERVIEW

JOB DESCRIPTION (paste below into description box):

ABOUT US

We are an established, growing US-based managed IT services provider (MSP) serving businesses in regulated industries. Small team, high standards, long-term client relationships. This role works directly with the owner as his right hand.

WHAT MAKES THIS ROLE DIFFERENT

This is not a task-list VA position. The owner will hand you entire workstreams in working sessions. For example: "own the renewal process for all of our client agreements" or "roll out updated employment agreements to our staff." Your job is to ask sharp questions, build the process, execute to 80-90% completion, and return with focused, decision-ready questions: "here is my thinking, do you want direction A or direction B?"

You will draft client-facing communication that requires care and nuance, keep billing and renewal cycles running on time, handle procurement and vendor follow-ups, and close every loop without being reminded.

You will also work alongside serious AI tooling (Claude) every day. No prior AI experience is required, but you must be the kind of person who picks up new tools quickly and gets excited about what they can do. Here, AI handles much of the drafting and computation; your judgment directs it. One sharp person in this role does the work of three.

WHAT YOU WILL OWN

- Client agreement renewals: the calendar, updated agreements, outreach, and follow-through (the owner handles only the largest strategic conversations)
- Client operations communication: order updates, pricing-change notes, and day-to-day client emails that need nuance and warmth
- Billing administration: monthly license invoicing, catching unbilled work, keeping invoices aligned with agreements
- Procurement: hardware quotes and orders, vendor follow-ups, license purchasing
- Internal projects: for example, rolling out NDAs and updated employment agreements via DocuSign, from research to signed
- Owner support: calendar, travel, payment deadlines, the details that keep a business running smoothly

YOU ARE PROBABLY A FIT IF

- You have 4+ years as an EA, operations coordinator, service coordinator, or account manager
- You have MSP or IT services experience (strongly preferred); you know what a PSA is, and ConnectWise, Autotask, or HaloPSA experience is a significant plus
- Your written English is excellent; you can take three tangled facts and turn them into one clear, warm, professional client note
- You have BUILT processes, not just followed them, and can tell us about one
- You flag things that look wrong instead of guessing
- You are comfortable being handed ambiguity and coming back with a plan
- You are excited about AI and learn new tools quickly
- You have reliable power and internet with a tested backup plan (we will ask)
- You can overlap US Mountain Time mornings by at least 4 hours (roughly 9pm-1am PH time, negotiable)

COMPENSATION AND SETUP

- $1,300-$1,700/month USD full-time, depending on experience, deliberately above typical market, because we are hiring judgment, not just hands
- Compensation review at 90 days, with real raise potential for demonstrated ownership
- Long-term role with growing responsibility; we are hiring for years, not months
- 13th month honored; paid PH holidays negotiable
- Shortlisted candidates complete a PAID work sample (about 2.5 hours, $40); we respect your time

HOW TO APPLY

Put the word COMPASS as the first word of your application subject line. Applications without it will not be read. This is our attention-to-detail filter; this role lives and dies on details.

Send a short note about yourself (not a template, we can tell) plus your CV, and complete these four items:

1. Describe a process you built from scratch at a previous job. What was messy before, and what did you create?

2. Tell us about a billing, order, or scheduling discrepancy you caught that nobody asked you to look for. What happened?

3. Scenario: a client's hardware order changed. Prices rose industry-wide since the original quote. The first machine chosen was somewhat over-spec for their needs. The replacement now being quoted is both a better fit AND a better machine, at a strong price given the market. Write the 3-6 sentence email to the client.

4. Include a short video (60-90 seconds, Loom or similar). No script, no slides, just talk: pick the most complex thing you manage in your current or most recent role, and explain it to us the way you would to a new colleague on their first day. We want to hear how you communicate when you have not rehearsed.

SKILL REQUIREMENT
Bookkeeping Project Management Executive Assistance
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