Executive Assistant & Accountability Partner

Executive Assistant & Accountability Partner

MatterCorp Automation
Type: Full Time
Compensation: $800–1,000/month
Hours: 40 hours/week, aligned to U.S. Central Time

Job Overview

I run a legal tech consulting practice called MatterCorp Automation. After 18+ years in enterprise IT at companies like AT&T and MasterCard, I moved into the legal tech space when a loved one went into private practice and needed IT support. Now I help law firms systematize their operations, and I’m working to scale the business beyond my current client base.

The challenge is that I’m stretched thin. I need someone who can provide the structure and follow-through that keeps everything moving — not just completing tasks, but holding me accountable to my own commitments. If things slip through the cracks, the business doesn’t grow.

That’s what this role is.

What This Role Actually Is

Your number one function is to be my accountability partner. That means:

• You own my calendar. Not just scheduling — making sure every meeting has context and prep so I know exactly why I’m there when I walk in.
• You own my inbox. Right now it’s cluttered. You triage, categorize, draft responses, and make sure nothing important gets buried.
• You run a daily 15-minute video standup every morning. We align priorities, surface what’s slipping, and you hold me honest about what I committed to the day before. This is non-negotiable — I need face-to-face accountability, not chat messages.
• You track every open commitment across clients, projects, and personal items — and you follow up relentlessly. When something has been dropped, you say so directly. Not a hint. Not waiting to be asked.
• You document everything as we build it. I move fast and leave breadcrumbs of documentation scattered across folders. Your job is to capture, organize, and make everything findable so no one spends thirty minutes hunting for something that already exists.
• You handle research and follow-through on whatever I delegate — booking flights, finding contractors, coordinating travel, preparing client materials.

This isn’t limited to business tasks. Work and life overlap in this role, and you’ll help systematize both.

Where This Goes

This role starts with me, but if I had to put a label on what you’ll become, it’s a process engineer.

To be clear: process engineer here means operational workflows, documentation, and execution cadence — not coding or building automations. I have a separate technical hire for that.

I also run technology and operations for a personal injury law firm. They have processes they know instinctively but have never documented. When a new case comes in, there’s a sequence of things that need to happen — but if they hired someone new tomorrow, there’s no playbook to follow.

My vision is to take what you learn from systematizing my world and apply it to client offices. Small law firms are so overloaded they can’t step back to document what they do. I want to place people into those offices to observe, document, and build structure around their operations.

That’s where you’re headed if you grow into this role. Strong performers can grow into an Operations Lead or Chief of Staff position.

What I Expect

I already have a technical VA handling Power BI dashboards, data work, and automation. This role is not technical — it’s operational.

You will use Microsoft Teams daily as our primary communication tool. We also use Zoom for recorded meetings. I’ll teach you Kanban boards and Agile methodology for tracking projects. You don’t need to know these now, but you need to be willing to learn.

I want the people who work with me to grow. Everything I teach you will be transferable to your career — even if that eventually means you outgrow this role. That said, I’m looking for someone who commits for at least one to two years.

I’m direct and informal. I drop the occasional F-bomb — it’s never directed at you and never out of anger. If that bothers you, we’re probably not a fit.

Requirements

• 3+ years supporting an executive, founder, or business owner remotely. Real partnership — you owned their calendar, inbox, and commitments. I will verify this on a live video call with a scenario you cannot rehearse.
• You can think on your feet. During our interview, you will be given a live chaotic Monday scenario. I’m looking for calm triage and clear prioritization without coaching. This is the single most important skill for this role.
• Respectfully direct communication. I need someone who will push back when they see a problem — not just say “yes sir.” If you’ve never challenged an authority figure in your career, this role will be very difficult.
• Strong written English. You’ll draft emails to attorneys and clients on my behalf.
• Reliable equipment. Working camera, stable internet, quiet workspace. Our daily standup is on video — this is not a chat-only role.
• Full 8-hour days aligned to U.S. Central Time (8 AM – 4 PM CT / roughly 9 PM – 5 AM Philippines). Night shift experience strongly preferred.
• No competing full-time roles. During scheduled work hours, this must be your only active commitment. Any side work outside hours must be disclosed and cannot conflict with MatterCorp.

Compensation

$800–1,000/month starting, based on experience. Weekly pay for the first month, biweekly after that. 30-day check-in and evaluation. 90-day decision point — if we both want to move forward, we discuss a salary adjustment.

13th month bonus is standard. All software and tools provided.

Healthcare support is a goal I’m actively exploring; not guaranteed yet.

Salary Alignment Requirement

The posted compensation range is firm: $800–$1,000 per month.

This role is budgeted strictly within this range. Applications requesting compensation outside this range will be automatically disqualified.

How to Apply

Do not send a generic application. I have rejected candidates with impressive resumes because their applications were clearly templates. I will know.

Include ALL of the following:

Include the phrase “structure creates calm” in your response. This confirms you read the full posting.

Answer these questions — be specific, not theoretical:
• What executive responsibilities have you managed? Name the tools. Describe a typical Monday. Tell me what went wrong and how you handled it.
• Describe a real time you helped someone regain control of a chaotic schedule. What was the situation, what did you do, and what specifically changed?
• Tell me about a time you disagreed with or pushed back on a boss, client, or authority figure. What happened and what was the outcome?
• What questions do you have for ME about this role? (If you say “none,” I will assume you didn’t think about it.)

Record a 2–3 minute video (Loom, Google Drive, YouTube unlisted) answering this:

“It’s Monday morning. Your boss has 47 unread emails, three client calls he hasn’t prepped for, a flight to book for next week, and he missed a deadline last Friday. He’s panicking. What do you do first and why?”

Show me how you think, not how you memorize.
Keep your answer to 2–3 minutes and use a numbered list to walk through your priorities.

Include your OnlineJobs.ph profile link.

State your salary expectation and earliest start date.

Applications without the video will not move forward.

IMPORTANT: Applications without the phrase “structure creates calm” will not be reviewed.