Remote Operations & Executive Support Specialist — US Entrepreneur

I’m a US-based entrepreneur running multiple projects - a technology consulting practice, a content brand, and ongoing enterprise IT work. I need a sharp, reliable right hand who can help me stay on top of everything. This is a long-term role for someone who wants stability, variety, and room to grow.
This is NOT a generic VA gig. You’ll be part operations specialist, part executive assistant, part content support. Every day is a little different, and that’s what makes it interesting.

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WHAT YOUR DAY LOOKS LIKE

Your day has two modes:

MORNING — ACTIVE MODE (2-3 hours)
You start 2-3 hours before US business hours. During this window you’ll:
• Open the enterprise ticketing system and review all open tickets
• Check for stale tickets that haven’t been updated and add status notes
• Follow up on pending items — if a pending status expires, take action or re-pend with a reason
• Follow up with external vendors/support teams on open service requests
• Identify and flag duplicate tickets for closure
• Draft customer-facing updates and internal status notes
• Build a clear daily briefing for me: what needs my attention today, in priority order
• Check my email and flag anything that needs a reply, with a draft if possible
When I sit down, everything is organized and I know exactly what to do.

AFTERNOON — MONITORING, CONTENT & ADMIN MODE (3-4 hours)
• Monitor incoming tickets, emails, and messages — handle routine items per the playbook, flag anything that needs my input via Telegram
• Help with my content brand — format posts, schedule content, post to social platforms, engage with comments, research topics I’m writing about
• Handle personal and business admin — track bills and due dates, organize documents, manage subscriptions, research purchases, schedule appointments, keep my life running smoothly
• Maintain documentation, SOPs, and trackers
• Take on whatever tedious-but-necessary tasks I don’t have time for — data entry, research, file organization, follow-ups, you name it
Some days are busy for all 6 hours. Some days the afternoon is quieter. But you always need to be responsive within 15 minutes during your shift.

THE THREE AREAS YOU’LL SUPPORT
1. Enterprise IT Operations (~2-3 hours/day)
This is the anchor of the role. You’ll work inside a ticketing system managing IT support i ---------- for a US healthcare organization. The work includes:
• Triaging and prioritizing support tickets
• Adding journal notes and status updates (minimum weekly on every open ticket)
• Monitoring pending statuses and acting on expiration reminders
• Following up with software vendors on open service requests and updating customers
• Catching duplicate tickets and flagging for closure
• Drafting professional, empathetic customer responses and concise internal notes
If you’ve worked in a BPO helpdesk, IT service desk, or healthcare support environment, you’ll recognize this immediately.
2. Content & Brand Support (~1-2 hours/day)
I run a content brand focused on ADHD, productivity, and AI-powered systems. You’ll help with the execution side:
• Formatting written posts for social media (X/Twitter, Threads, LinkedIn)
• Scheduling and publishing content using scheduling tools
• Light engagement — responding to comments, liking relevant posts
• Researching topics, pulling data or references for articles I’m writing
• Organizing content drafts and assets in shared folders
• Helping with any repetitive content production tasks
You don’t need to be a content strategist. I handle the ideas and writing. I need someone who takes a finished draft and makes it live in the world.
3. Personal & Business Admin (~1 hour/day)
• Tracking bills, due dates, subscriptions, and renewals
• Organizing documents (tax docs, receipts, contracts)
• Researching products, services, and vendors when I need to make a purchase decision
• Scheduling appointments and managing calendar items
• General inbox management — sorting, flagging, drafting replies
• Any other admin tasks that eat time and don’t require my brain specifically

WHO WE’RE LOOKING FOR
Must-haves:
• Excellent written American English — indistinguishable from a native speaker. You’ll draft communications going to US clients and stakeholders.
• 2+ years in BPO, remote support, helpdesk, executive assistant, or VA roles with a single employer or structured environment.
• Experience with ticketing systems — ServiceNow, Jira, Zendesk, Freshdesk, Cherwell, or similar. You understand ticket lifecycle: open, in progress, pending, resolved.
• Ability to context-switch — in a single morning you might update a support ticket, schedule a social media post, and research a tax deadline. You handle variety without getting scattered.
• Self-management skills — you work 6 hours/day with a daily check-in, not constant supervision.
• Reliable internet and a quiet workspace.
• Able to start your shift 2-3 hours before 9am US Eastern Time.
Strong nice-to-haves (any of these move you to the top):
• Healthcare IT or US healthcare BPO experience
• Familiarity with EHR/EMR systems or clinical IT environments
• ITSM/ITIL background
• Social media management experience — especially X/Twitter, Threads, LinkedIn
• Experience using AI tools (ChatGPT, Claude, etc.) to work faster — drafting, summarizing, researching
• Experience supporting an entrepreneur or executive as a personal/executive assistant
• Familiarity with tools like Notion, Google Workspace, Canva, Buffer/Hootsuite, Loom

WHAT KIND OF PERSON THRIVES HERE
You’re the executor. You take a plan and make it happen. When you see a ticket going stale, you update it before being asked. When there’s a post ready to publish, you format it and schedule it without waiting for a reminder. When a bill is coming due, you flag it three days early. You find satisfaction in a clean queue, an organized tracker, and a to-do list with everything checked off.
You’re not looking for a job where you do the same thing for 8 hours straight. You like variety. You want to work closely with someone, understand how they think, and become the person they can’t run their life without.

SCHEDULE & PAY
• Hours: 6 hours/day, Monday-Friday (30 hours/week)
• Rate: $7-$9/hr USD depending on experience
• Raise structure: Performance review at 30 days with a rate increase for strong performers
• Payment: Weekly via Wise, paid every Friday
• Start: ASAP — paid 2-week trial period
• Duration: Long-term (12+ months for the right person)
• Growth: As trust builds, the role expands. This can become a true chief-of-staff position for the right person.
• Equipment: You provide your own computer and internet