Senior Executive Assistant to Founder — AI, Operations & Personal Support

I’m the founder of a growing marketplace that helps businesses and individuals find financial professionals.

I’m looking for a senior Executive Assistant who can become my operational right hand.

This is not a basic virtual assistant role, and I am not looking for someone who waits for a daily task list.

I move quickly, have a lot happening at once, and need someone who can bring structure to that environment, keep track of commitments, make good decisions independently, and make sure important things actually get finished.

The goal of this role is simple: reduce the number of things that require me.

WHAT YOU WILL OWN

You will gradually take ownership of:
- Managing and triaging my inbox
- Drafting and eventually handling routine communications on my behalf
- Calendar management, scheduling, conflicts, and meeting preparation
- Turning meetings, transcripts, voice notes, and ideas into clear tasks and follow-ups
- Making sure things I committed to actually happen
- Following up with customers, vendors, contractors, partners, and other stakeholders
- Travel planning, flights, hotels, transportation, reservations, and itineraries
- Event logistics, guest lists, invitations, RSVPs, and follow-up
- Personal administrative tasks such as gifts, appointments, purchases, and travel
- Tracking invoices, payments, outstanding requests, and administrative loose ends
- Coordinating with contractors and developers when something needs to be fixed or completed
- Supporting outreach and maintaining accurate CRM/task information
- Scheduling approved social content and helping prepare basic assets when needed
- Researching questions and presenting recommendations rather than simply sending me links
- Building systems, SOPs, and processes as you learn how I operate
- Identifying repetitive work that can be improved or eliminated with AI and automation

You will have access to sensitive business and personal information. Judgment, discretion, security, and attention to detail are extremely important.

AI AND AUTOMATION ARE A MAJOR PART OF THIS ROLE

I am specifically looking for someone who is already highly proficient with AI.

Using ChatGPT to rewrite an email is not enough.

You should be comfortable using tools such as ChatGPT and Claude every day and ideally have experience with tools such as Zapier, Make, n8n, ClickUp, Notion, Slack, Google Workspace, Fireflies, or similar systems.

I want someone who sees a repetitive process and asks: “Why are we still doing this manually?”

Strong candidates should be able to show examples of workflows, automations, systems, agents, or processes they personally built or materially owned.

You do not have to be an engineer. You do need to be resourceful enough to figure things out.

WHAT I AM LOOKING FOR

Ideally, you have:
- 5+ years of professional experience
- 3+ years directly supporting a founder, CEO, entrepreneur, or senior executive
- At least one role where you stayed long enough to earn significant trust and responsibility
- Experience working directly with U.S.-based executives
- Excellent spoken and written English
- Strong executive communication skills
- Experience owning inboxes, calendars, follow-up, travel, projects, and confidential information
- Demonstrated use of AI and automation beyond simple content generation
- Strong project-management and organizational ability
- Excellent judgment about what you can handle independently versus what needs to be escalated
- The confidence to manage up and respectfully push back when appropriate
- The ability to work full-time, Monday–Friday, approximately 9:00 AM–5:00 PM U.S. Eastern Time, with occasional flexibility around travel and events
- Reliable internet, equipment, and a backup plan for power/connectivity

THE PERSONALITY THAT WILL SUCCEED HERE

You are calm when things are moving quickly. You do not become overwhelmed because priorities changed. You do not need every process documented before you can begin. You research before asking questions.

When you encounter a problem, you prefer to come back with: “Here are the three options. I recommend option two because…” rather than: “What do you want me to do?”

You are comfortable reminding a founder about things, following up repeatedly when necessary, protecting their time, and telling them when they are creating too many priorities.

THIS ROLE IS PROBABLY NOT A FIT IF

- You need detailed step-by-step instructions for most tasks
- Your AI experience is primarily asking ChatGPT to draft emails
- You become uncomfortable when priorities change
- You prefer a highly structured corporate environment
- You are uncomfortable receiving direct feedback
- You routinely need your executive to remind you about follow-ups
- You are looking to work multiple overlapping full-time jobs

COMPENSATION

$2,000–$2,500 USD per month, depending on experience and demonstrated ability.

Full-time, long-term role.

There will be a compensation and performance review after your first 90 days.

Benefits include 10 paid vacation days after 90 days, paid U.S. holidays, and a long-term growth opportunity.

HOW TO APPLY

Start your application with the words:

FOUNDER OPS

Applications that do not include those words will not be reviewed.

Please include:

1. Your resume or LinkedIn profile.

2. A 2–3 minute video answering:
- Who is the most demanding founder or executive you have supported?
- What did they trust you to handle independently?
- What is one system, automation, or workflow you personally built or significantly improved?
- What AI and automation tools do you personally use today?
- What are your current work commitments, and when could you begin working full-time Eastern Time?

3. Tell me your desired monthly salary.

4. Answer this scenario in no more than 200 words:

It is Friday at 4:00 PM. Your executive has 15 important unread emails, three people waiting on promised documents, two appointments that still need to be scheduled, and has not given you any additional instructions. What do you do?

Candidates who advance will complete a paid, two-hour work sample designed to test judgment, prioritization, communication, ownership, and practical AI/automation ability.

Finalists will also be asked for professional references.

I am looking for someone who wants to become deeply trusted, learn the business, take on increasing responsibility, and build a long-term working relationship with a founder.