Executive Assistant

Full-time Independent Contractor (remote)
Experience Level: Mid–Senior (5+ years supporting founders/entrepreneurs)
Time Zone: US business hours
Language: Excellent written and spoken English (non-negotiable)

Role Overview

We are seeking an exceptional Executive Assistant to serve as the central hub for both our business operations and personal lives.

This is not a typical assistant role. We need a proactive, assertive, independent thinker who anticipates needs, solves problems, and executes without hand-holding. You must be comfortable pushing things forward and managing us when necessary to avoid blocking progress.

Required Background & Personality

5+ years supporting multiple busy founders/entrepreneurs
Experience in lean, fast-moving, unstructured startup environments
Comfortable wearing many hats and figuring things out independently
Assertive communicator who leads with best practices
Proactive executor — not reactive
Entrepreneurial mindset; thinks like a business owner

Core Responsibilities

1. Recruiting & Contractor Management

Post roles across LinkedIn, Upwork, Fiverr, Indeed, Facebook groups, and online communities
Actively source candidates using filters and outbound outreach
Write compelling job posts and outreach messages
Create role-specific interview questions
Conduct screening interviews and analyze candidate calls
Deliver organized shortlists with clear recommendations
Negotiate rates and terms
Fully manage contractor relationships end-to-end

2. Project & Operations Management

Build and manage a central task hub (ClickUp, Notion, Asana, or similar)
Act as primary manager for contractors and service providers
Provide proactive daily/weekly status reports
Follow up relentlessly to keep projects moving
Manage competing priorities and define what matters most
Coordinate with billing providers (phone carriers, insurance, IRS, recruiting back-end, etc.)
Maintain document storage, communication channels, and password systems

3. Social Media & Personal Brand (LinkedIn Primary)

Research and build LinkedIn content strategy
Audit and update LinkedIn profiles
Draft and schedule LinkedIn posts (target: 2 per day)
Create simple graphics in Canva
Engage via comments, connection requests, and DMs
Track and report performance metrics

Later Phase:

Launch and manage newsletter (Beehive or similar)
Support YouTube research, scripting, editing, AI repurposing
If needed, source and manage video editing contractors

4. Research & Business Support

Conduct business model research and brainstorming
Identify and outreach to potential mentors
Prepare tailored questions for mentor calls
Research courses, books, experts
Take courses, summarize, and implement learnings
Personal brand research and strategy support
(Bonus) Offer creation and ideation support

5. Client & Administrative Support

Organize Google Drive, OneDrive, Smartsheets
Edit and create Excel, Word, and presentation materials
Manage administrative tasks across Zoho, LinkedIn, Email, Upwork
Maintain cloud storage and course uploads
Inbox and calendar management
Ensure bookkeeping is completed on time
Manage receipts and ad hoc expense reports

Personal Support Responsibilities

A significant portion of this role includes managing our personal lives.

Home & Lifestyle

Manage groceries, chef coordination, Amazon returns
Create schedules for in-person assistant
Schedule appointments and reservations
Organize meditation content

Research & Planning

Product research and gift purchasing
Travel planning (flights, hotels, full itineraries)
Moving research and coordination
Event/conference research and booking
Wedding planning support (Dominican Republic)

Vendor Sourcing & Vetting

Source and screen home service providers
Conduct interviews and deliver vetted shortlists
Ongoing coordination and relationship management

Dog & Miscellaneous

Vet and manage trainers and appointments
List and manage Facebook Marketplace items

Essential Qualities

Exceptionally proactive and independent
Highly organized project manager
Strong recruiting capability
Detail-obsessed; polished, error-free work
Clear, frequent communicator with proactive updates
Scrappy and resourceful in unstructured environments
Fast, efficient, reliable, and capable of deep focused work
AI-savvy but discerning — uses tools intelligently and vets outputs

What Success Looks Like

Minimal direction required; tasks move forward without follow-up
Projects run smoothly without our involvement
Issues flagged early with researched solutions
Flawless, polished execution
End-to-end recruiting handled independently
Clear, digestible status updates provided proactively
Our lives feel noticeably easier
Complete trust in judgment and execution

What We Want to Avoid

Do not submit candidates who are:

Inexperienced supporting founders
Reactive or needing micromanagement
Poor at follow-through
Dependent on AI without judgment
Frequently requiring revisions
Easily distracted or unable to focus deeply
Reluctant to push for what they need

Tools & Platforms

Experience with or willingness to learn:
LinkedIn, ClickUp/Notion/Asana, Upwork, Fiverr, Gmail/Outlook, Canva, Instacart, ChatGPT/Claude/Perplexity/Fathom, Beehive, OneDrive/SharePoint, Zoho, Smartsheets, Microsoft Office.

Executive Assistant - 18256