Compensation
$700-$1200 (based on experience)
About This Role
We are looking for a highly organized, proactive, and resourceful Executive & Personal Assistant to support a Creative Director managing multiple creative projects and a growing freelance web design business. This is a dual-purpose role spanning professional support and personal life management. The ideal candidate takes ownership of tasks, runs with them as far as they can, and knows exactly when to bring something back for a final decision or direction.
AI is a core part of how we work — not a nice-to-have. If you’re not using it yet, you need to be genuinely excited to learn.
Who You’re Supporting
You’ll be working directly with a Creative Director who oversees multiple ongoing creative projects across design, web, and video. He also runs a freelance web design business targeting small businesses. Outside of work, he is a husband and father who needs help keeping life running smoothly.
What You’ll Do
Professional / Creative Support
- Take tasks as far as possible independently — research, organize, draft, prepare — then present the work for final direction or sign-off
- Use AI tools (ChatGPT, Claude) to draft content, summarize information, build outlines, and accelerate every task
- Help build and refine automations that reduce repetitive work across projects and workflows
- Assist in creating Claude skills and custom AI workflows that make day-to-day operations faster and smarter
- Track and manage open to-dos, deadlines, and project status so nothing falls through the cracks
- Draft communications, creative briefs, summaries, and project outlines ready for review
- Support light creative tasks — writing copy drafts, organizing files, formatting presentations, basic work in Canva
- Manage calendar scheduling and meeting prep
- Conduct research on tools, trends, and industry topics and deliver organized findings
Freelance Web Business Support
- Build and maintain a prospecting pipeline for small business web design clients
- Execute cold outreach via email and phone — scripted cold calls, follow-up sequences, DM campaigns
- Research target businesses, find decision-maker contacts, and keep the CRM updated
- Prepare proposals and intake forms up to the point where final review is needed
- Use AI to draft outreach copy, personalize messages at scale, and speed up research
Personal & Family Assistance
- Coordinate and track children’s school schedules, assignments, deadlines, and teacher communications
- Conduct or assist with tutoring sessions via Zoom (reading, writing, math — based on grade level)
- Use AI tools to create lesson plans, study guides, and practice exercises for tutoring sessions
- Help manage household finances — track expenses, organize bills, prepare budget summaries, coordinate with vendors
- Research services, vendors, or solutions for household needs and present a clear recommendation
- General calendar management and life logistics — appointments, reminders, travel research
You Are a Great Fit If You…
- Are fluent in English (written and spoken) — this is non-negotiable
- Have 2+ years of experience as a VA, executive assistant, or operations coordinator
- Are actively using AI tools like ChatGPT or Claude in your daily workflow — or are genuinely hungry to learn and adopt them fast
- Understand or are willing to learn how to build automations and custom AI workflows using tools like Claude Code and Claude’s skill/agent system
- Take full ownership of tasks — you don’t wait to be told every step, you figure it out and bring back a finished product
- Know when to stop and ask rather than guess on something that requires a decision
- Are comfortable jumping between tasks — from a Zoom tutoring session to cold calling to scheduling an appointment
- Have experience with tools like Google Workspace, Slack, Canva, Zoom, Notion (not all required, but familiarity matters)
- Have a quiet, professional home setup with reliable internet for video calls
Bonus Points For…
- Hands-on experience with ChatGPT, Claude, or other AI assistants in a work setting
- Experience building automations (Zapier, Make, or AI-native tools)
- Familiarity with Claude Code or prompt engineering
- Prior experience with Webflow, Figma, or web design
- Background in sales, outreach, or appointment setting
- Experience tutoring children (elementary or middle school level)
- Familiarity with creative or marketing project workflows
- Bookkeeping or personal finance management experience
What to Expect
- Hours: 20–40 hours/week depending on arrangement
- Communication: Primarily via Slack and Zoom
- Schedule: Flexible with overlap during US Eastern Time hours preferred
- Pay: Discussed during interview based on experience and hours
How to Apply
Send a short video (2–3 minutes) or voice memo introducing yourself and answering:
1. What’s your experience as an assistant or VA?
2. Have you ever done cold calling or sales outreach? If yes, describe it.
3. Are you comfortable doing Zoom sessions with kids?
4. What AI tools do you currently use, and how? If none — how eager are you to learn and what have you taught yourself in the past?
Then attach your resume or a brief written summary of your background.
We’re looking for someone who runs with a task, gets it 90% done, and brings it back sharp. If you use AI to work smarter, take initiative, and know when to ask — you’ll thrive here.
Job Types: Full-time, Part-time
Work Location: Remote
