Sr. Virtual Assistant to CEO

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TYPE OF WORK

Full Time

SALARY

1500

HOURS PER WEEK

40

DATE UPDATED

Jul 26, 2026

JOB OVERVIEW

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
Remote · Full-time

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.

Writing and positioning. You'll draft the things that carry my name: sponsor emails, speaker bios in short, medium, and long, intro copy for hosts, one-sheets for events, and follow-ups to executives. I edit. I don't start from a blank page.

AI and building. Use AI to move faster — drafting, research, summarizing transcripts — and check the work before it reaches me. Keep the prompts we rely on somewhere both of us can find them. When we need a small internal tool, a tracker, an intake form, a simple page, you build it with AI coding tools and ship something that works rather than a proposal for something that might.

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.

THE RHYTHM OF THE JOB

Every day:
- Work my inbox. Triage, file, and draft replies for my review. Nothing sits unanswered past 24 hours, including the ones you have to chase someone else to answer.
- Keep the calendar true. Confirm tomorrow's meetings today. Put prep material in the invite before I have to ask where it is.
- Run my meetings around me. Agenda in the invite beforehand, notes or a transcript summary after, action items sent out the same day.
- Publish the daily Substack article on schedule. Answer the Skool community.
- Handle travel as it breaks. Flight moves, seat changes, upgrade windows, PreCheck on every ticket.
- Send me an end-of-day note: what closed, what's stuck and why, what needs a decision fro ---------- .

Every week:
- Monday morning, put the week in front of me on one page. Meetings, travel, deadlines, and who I need background on before I walk in.
- Sponsorship work. Sequences in HubSpot, outreach in Apollo, LinkedIn follow-up when email goes quiet, and a pipeline update I can read in two minutes.
- Get vendors on the phone. Not email tag. Quotes in hand, compared, with a recommendation.
- Draft the week's emails, bios, and one-sheets and send them to me for edits.
- Submit applications for podcasts, panels, and stages, and track what came back.
- Build or fix one small internal tool we need, using AI coding tools.
- Reconcile receipts and expenses while the details are still fresh.

Every month:
- Audit the software. Cancel what nobody opened. Handle the bank and vendor calls that come with canceling, and keep a renewal calendar so nothing auto-charges by surprise.
- Renegotiate. Pull three competing quotes on anything recurring that looks high.
- Check every deadline that can't move: CLE, bar and licensing portals, filing dates. Flag them 30 days out, not the week of.
- Look 60 to 90 days ahead on travel and book while fares and award seats still exist. One-sheet per trip.
- Send the gifts, flowers, and thank-you notes for the month without being reminded.
- Handle family logistics on the calendar: camps, children's activities, appointments.
- Move Black Women Sell Live forward against the timeline. Vendors booked, interpreters priced, insurance quoted, volunteer packets built, workbooks ordered, sponsor swag shipping to the right addresses.
- Audit logins and account access so nothing breaks at the worst possible ---------- nt.
- Give me the numbers: outreach sent, applications submitted, content published, money saved on vendors.

Volume shifts around launches and the conference. The week before Black Women Sell Live looks nothing like a normal week, and I need someone who plans for that instead of being surprised by it.

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 AI tools, 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 ---------- AND ---------- 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.

SKILL REQUIREMENT
Customer Support Email Management English
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