Senior Virtual Assistant

Sr. Virtual Admin (Reports to CEO) - $1,500 - $1,800/Month USD Full Time

Executive Assistant to the CEO

Company: Speak Your Way To Cash® (three-time Inc. 5000)

Reports to: Ashley Kirkwood, Founder & CEO

The short version

I run a sales training company, a law practice, a foundation, and a luxury travel company, and I have a family. I need one person who can hold the details so I don't have to. That means booking the surgeon and the yacht charter in the same afternoon, chasing an attorney for a fee agreement without being reminded, and telling me when something is off before I notice it myself.

This is not a role where I assign a task and then check on it three times. If you need to be followed up with, this is the wrong job.

What you'll actually do

Events. Our annual conference, Black Women Sell Live, is the biggest thing we do. You'll source and book vendors, price accessibility services like certified ASL interpreters, get event insurance quotes, coordinate volunteers and their packets, order workbooks and journals, and make sure sponsor swag ships to the right addresses on time.

Sponsorship support. Build sequences in HubSpot, run outreach in Apollo, identify the right three contacts at each target organization, draft pitch emails for my review, and follow up on LinkedIn when email goes quiet. You won't be closing sponsors. You will make sure nothing sits in a spreadsheet doing nothing.

Content operations. Daily Substack articles get written and revised on a schedule. Community messages in Skool get answered every day. Show transcripts get compiled and organized. Applications for podcasts, panels, and stages get submitted and tracked, not started and abandoned.

Legal and professional admin. I'm a licensed attorney, so there's a layer of work most EAs never touch: CLE deadlines, bar and licensing portals, sourcing outside counsel in states where I need local representation, and helping the firm hire. You don't need a legal background. You do need to treat a filing deadline as immovable.

Tech and vendor cleanup. Audit our software, cancel what we don't use, handle the bank and vendor calls that come with it, and keep logins and account access working.

Travel. Flights, upgrades, seat assignments, PreCheck on every ticket, one-sheets for each trip with flight, hotel, and car in one place. When a return flight disappears and the airline wants two thousand dollars to fix it, you find the workaround before you bring it to me.

Calendar and personal logistics. My calendar is the center of everything. You'll keep it accurate and color-coded, book appointments, arrange gifts and flowers for the people who matter to us, book restaurants, and handle family logistics like camps and children's activities.

What makes someone good at this

You finish things. When I hand you something, the next thing I hear about it is that it's done, or that you hit a wall and here are the two options you found.

You can price and negotiate. Several of the quotes we get back are two or three times what the work is worth. I want someone who notices that, goes and finds three more, and comes back with a recommendation.

You write clearly and professionally. A lot of what you send goes to sponsors, attorneys, and executives with my name attached to it.

You're comfortable with HubSpot, Apollo, Google Workspace, and learning whatever else we use. If you've never used one of them, say so and tell me how fast you pick up software.

You keep confidences. You'll see legal matters, financial information, and family details. That never leaves the room.

You are honest about mistakes, quickly. Things go wrong in this business every week. What I can't work with is finding out late.

How to apply

Email [Confidential Information] AND [HIDDEN TEXT]

with the subject line: YOUR NEXT EA

Send a résumé AND send a Loom video (unlisted is fine) that covers two things:

1. The assignment. I have a flight booked to Martha's Vineyard for August 12–15, 2026. Every hotel on the island is sold out. Tell me where I should stay and how I'm getting around once I'm there. Be specific — names, prices, availability you actually checked, how the booking would work, what the backup is if your first option falls through. I want to see how you solve a problem when the obvious answer isn't available.

2. Your experience. Tell me where you've done this work before. Who you supported, what you owned, and one situation you handled end to end without being managed through it.

I will not follow up asking for missing pieces. If the assignment isn't answered in the video, the application is done. The way you handle this is the same way you'd handle the job, and that's exactly what I'm evaluating.