Senior Executive Assistant / Operations Specialist

Senior Executive Assistant / Operations Specialist

The Short Version

We're looking for two people: one to work with Matt, one with Nathan. You'll be a force multiplier for one of our founders across two businessesOPTIO (pitch deck consultancy, $3B+ raised for clients) and Secret Agency (website subscriptions for startups).

Compensation: Paid in USD. We pay 2-3x typical Philippines VA rates because we expect exceptional performance.

This job exists because the last person got promoted. Our previous EA became so valuable that we promoted him internally. He'll be training you.

This is not a gig. This is not a stepping stone. I want to work with you for 20 years.

If that sounds crazy: we have 10 employees. In four years, no one has voluntarily left. The people who are good stay, grow, and get paid more every year.

About the Businesses

OPTIO (www.optio.io) helps startups raise venture capital. We make pitch decks. Our clients are founders raising money for everything from AI defense companies to film studios to national daycare chains. We're small, profitable, and growing fast.

Secret Agency is our newer venturemonthly website subscriptions for funded startups. Same obsession with quality, different deliverable.

About Us

Matt Gore Former startup founder, ex-management consultant (BCG), now running these two businesses. His wife is a surgical resident, which means she works even harder than he does. They have a 6-month-old baby.

Nathan Wallace Partner at OPTIO, storytelling expert who's helped founders raise over $2 billion. He leads client relationships and is scaling Secret Agency alongside Matt. Nathan spent a year living in Manila to work alongside and train our Philippines team in person.

We're hiring two Senior EAsone to work directly with Matt, one with Nathan. Same role, same expectations, different principals.

Our Philippines team members are real teammates, not outsourced labor. We have four teammates in the Philippines today. This year, we're flying the Philippines team to Texas for a company retreat at Matt's ranchcowboy hats, campfires, steaks, and guns. When we say we take care of our people, we mean it.

We're both buried. Growing faster than our systems can handle. Missing things we shouldn't miss. We each need a force multiplier.

What You'd Actually Do

You will ride shotgun in every meeting. Not reviewing notes aftersitting in the room (virtually), capturing action items, sending follow-ups before the call ends. We'll spend hours together every single day.

You will send emails as us. Not drafts for reviewactual emails, in our voice, to clients, partners, and vendors. Some of these decisions will be worth tens of thousands of dollars. You need the judgment to make them without asking.

You will own our inboxes. Reply to what you can handle, escalate what you can't, and never let anything slip.

You will make high-stakes decisions. When to push back on a client, when to offer a discount, when to escalate. You'll have real authority because we'll trust your judgment.

Executive support:

Send a Daily Brief each morning: top priorities, key meetings, pending decisions, critical follow-ups

Own calendars end-to-end: schedule meetings, ensure buffer time, resolve conflicts, confirm agendas

Prep for every meeting: who we're talking to, what we need to accomplish, relevant context

Financial operations:

Generate and send invoices via QuickBooks

Track payment status and follow up on overdue invoices (politely but relentlessly)

Send regular financial updates: cash position, incoming payments, outstanding invoices

Process reimbursements and validate receipts

Contracts and legal:

Generate contracts using approved templates, customize scopes and terms

Send contracts via DocuSign, track signature status, follow up as needed

Ensure executed agreements are properly stored

HR and payroll:

Prepare and issue team member contracts

Manage onboarding documentation for new hires

Project oversight:

Maintain a live view of all active projects and clients

Flag delays, scope creep, or resourcing issues before they become problems

Facilitate handoffs between teams (strategy, design, dev)

Track deliverables vs. commitments

Daily operations:

LinkedIn engagement: commenting, connection requests, message responses

CRM updates: move deals through stages, log notes, trigger follow-ups

Inbox zero: every email addressed, archived, or escalated by end of day

Content creation:

Draft and post content on LinkedIn and X (Twitter)

Light research on prospects, industries, competitors

Potentially edit podcasts and video content

Personal support:

Coordinate with Matt's wife's schedule for date nights and personal logistics

Handle mail, parking tickets, utilities, subscriptions, and miscellaneous life admin

Interface with our US-based house manager as needed

Track tax payments, filing deadlines, and required documentation

Systems improvement (ongoing):

Maintain clean, organized systems across Slack, QuickBooks, DocuSign, and shared drives

Continuously improve SOPs, workflows, and templates

Identify inefficiencies and propose solutions proactively

This role requires extraordinarily high EQ. You'll be representing ussometimes explicitly as an assistant, sometimes invisibly as one of us. You need to know the difference and get both right.

Who Thrives in This Role

You're AI-native. Your first question on any task is can I use AI to do this better and faster Your second question is can I automate this so it happens automatically You have opinions about which models are best for what. You're not experimenting with AIyou're already using it every day and can't imagine working without it.

You follow through relentlessly. When something needs to get done, you don't let it go. The insurance company hasn't responded in a week You're calling them again. The contract is sitting unsigned You're following up today. You don't let things slip through the cracks because it physically bothers you when they do.

You're friendly and persistent. You can send a fifth follow-up email without being annoying. You can push back on someone while keeping the relationship warm. You're firm but kind.

You're a finisher. You don't just start thingsyou close loops. You'd rather do something fast and imperfectly than let it sit. You hate when tasks linger.

You're detail-obsessed. You catch typos in contracts. You notice when dates don't match. You remember that a client mentioned their kid's birthday. This isn't a chore for youit's satisfying.

You can write in someone else's voice. You'll study how we communicatetone, phrasing, what we'd say yes to and what we'd push back onand send emails as us that we couldn't distinguish from our own.

You have extraordinary emotional intelligence. You'll be making decisions that affect client relationships worth tens of thousands of dollars. You need to know when to escalate, when to handle it yourself, and how to read a situation before it becomes a problem.

You're a systems thinker. When you do something twice, you wonder if there's a better way. You build templates. You automate. You make things hum.

You move without being pushed. You see a problem and fix it. You don't wait for permission. You'd rather ask forgiveness than approval.

You're intellectually curious. You'll be learning about defense tech one day and childcare franchises the next. That sounds interesting to you, not exhausting.

Requirements

Prior experience as an EA, VA, or operations specialistwe need someone who has done this successfully before

Heavy AI useryou already use AI tools daily and have opinions about which models work best for different tasks (Claude vs. ChatGPT vs. Geminiand why)

Excellent written and spoken Englishyou'll be sending client-facing emails as the founders and joining calls with US-based clients

Full-time US hoursMountain Time (8am-5pm MT) or East Coast hours depending on which founder you're matched with. This is non-negotiable.

Quiet, professional workspace for video callsyou'll be on camera in meetings throughout the day

Strong references from former bosseswe'll ask to speak with them

Experience with: Google Workspace, Slack, Notion (or similar), CRM tools

Comfortable learning new platforms quickly (QuickBooks, Gusto, DocuSign, etc.)

Reliable high-speed internet

Bonus points:

Experience in consulting, startups, or professional services

Familiarity with Webflow or PowerPoint

You've worked directly with a founder or executive before

Experience with podcast or video editing

Culture

We take care of each other. This isn't a platitudeit's how we operate. A few examples:

Nathan and Matt actively compete to take the blame for mistakes in client meetings. If Matt messes up, Nathan will claim it was his fault. If Nathan drops something, Matt will jump in and take responsibility. We protect each other.

We practice positive gossip. If Nathan thinks someone did great work, he'll tell Matt, and Matt will pass it on: Hey, Nathan said your deck was outstanding. We build people up behind their backs.

We celebrate when people take vacations and have big life events. We want you to have a full life outside of work.

We work hard and we sabbath. During work hours, we're all-in. Outside work hours, you're not supposed to check emails. Take real vacations. Work hard when you're at work.

Compensation & Benefits

Annual salary review with performance-based increases

Discretionary performance bonus

Health & Statutory

Health insurance reimbursement (employee + dependents)

PhilHealth reimbursement

SSS reimbursement

Pag-IBIG (HDMF) reimbursement

Equipment & Software

MacBook provided

All necessary software and AI tools covered

Time Off

15 days PTO annually

10 days sick leave annually

Growth & Community

Professional development support

Company retreat in Texas this yearwe're flying our Philippines team to Matt's ranch for cowboy hats, campfires, steaks, and guns.