Executive Assistant

Executive Assistant for Entrepreneur

Part-Time (Starting 5 hrs/week) | 1099 Contract | Virtual with Occasional Local Meetings and Tasks

About the Company/Owner

Seeking a proactive, tech-savvy Executive Assistant (EA) to support an entrepreneur with a combination of business and personal tasks. Owner focuses on high-level strategies and is seeking someone to assist with tasks that will enable continued growth and support for the owner.

The Role

This position starts at 5-10 hours per week with the opportunity to expand based on performance and mutual fit. You'll work primarily remotely with occasional in-person meetings (local candidates preferred). This is a 1099 contractor position- LLC preferred but will consider individuals.

Important: You'll be required to sign an NDA and BAA (Business Associate Agreement) to protect confidential information. However, you will NOT handle HIPAA-protected patient information or clinical documentation- your role focuses on supporting the owner with executive-level business operations, administrative/office tasks, and personal tasks.

Initial Responsibilities (First 90 Days)

• Calendar management and appointment coordination (business and personal)
• Travel planning and logistics
• Vendor communication and coordination
• Meeting preparation and communication
• System set-up and maintenance
• Document organization and file management
• Research and information gathering
• Process documentation and improvement
• Personal errands and task coordination as needed

Growth Opportunities

As you demonstrate competence, trust, and the partnership proves successful, responsibilities may expand to include:

• Social media content creation and management
• Marketing project coordination
• Event planning and coordination
• Household management support
• Special projects and business development initiatives
• Photography and content creation for practice marketing

Required Qualifications

• Minimum 3 years of experience in an executive assistant, personal assistant, or similar administrative role
• AI proficiency: Must actively use AI tools (ChatGPT, Claude, Perplexity, etc.) to enhance productivity, draft communications, conduct research, and streamline workflows
• Discretion and confidentiality: Comfortable handling sensitive business and personal information with the utmost level of security
• Local to Lake Ridge, VA for occasional in-person meetings, local tasks, and local errands
• LLC preferred (but will consider exceptional individual contractors)

Must-Have Skills:

• Exceptional communication: Professional, warm, and clear written and verbal communication with vendors, colleagues, and personal contacts
• Stellar time management: Ability to prioritize competing demands and meet deadlines consistently without micromanagement and without excuses
• Superb organization: Systems-oriented approach to managing information, processes, and multiple moving parts while utilizing technology (such as AI) to supplement work demands

Proficiency with:

• Google Workspace and Microsoft 365
• Calendar management across multiple platforms
• Project management tools (Trello)
• AI tools for task automation, research, and efficiency
• Video conferencing platforms (Zoom, Google Meet, Teams, etc.)

High Emotional IQ:

• Self-awareness: You recognize your own emotions, strengths, limitations, and how they impact your work and interactions
• Self-regulation: You remain calm under pressure, adapt to changing priorities, and maintain professionalism even in stressful situations
• Empathy: You can read between the lines, understand unspoken needs, and anticipate what support is needed before being asked
• Social skills: You build rapport easily, communicate with tact and diplomacy, and navigate diverse personalities and situations with grace
• Motivation: You're intrinsically driven to do excellent work, take initiative, and find fulfillment in supporting others' success

Bonus Skills (Not Required, But Highly Valued)

• Photography and photo editing
• Social media content creation and management (Instagram, Facebook, LinkedIn)
• Graphic design (Canva, Adobe Suite)
• Video editing for social media
• Website and CRM management (WordPress, Go High Level)
• Email marketing platforms (Mailchimp, Mailer Lite)
• Event planning experience

Ideal Candidate Profile

You're a self-starter who thrives on completing tasks efficiently and with excellence. You anticipate needs before being asked, communicate proactively and with brevity & clarity, and take genuine pride in making someone else's life easier. You see AI as a powerful assistant (not a replacement) and regularly incorporate it into your workflow to work smarter, not harder.

You're equally comfortable booking a business meeting and coordinating a personal appointment. You handle sensitive information with the utmost discretion and understand that supporting a busy entrepreneur means wearing many hats- from strategic business tasks to practical personal coordination.

You're comfortable working independently, but you know when to ask questions. You don't need hand-holding, but you do need clear priorities. You bring solutions, not just problems. You problem solve instead of making excuses.

What Success Looks Like

• The entrepreneur has more time to focus on clinical work and strategic growth
• Tasks are completed accurately and on time without reminders
• Communication is clear, proactive, and professional
• Systems and processes become more efficient over time
• You become a trusted partner who can handle anything thrown your way

Compensation & Details

• Starting rate: $25+/hour (based on experience and skills)
• Start Date: January 2026
• Structure: 1099 contractor position (LLC preferred)
• Hours: Starting at 5-10 hours/week
• Growth potential: Up to 15-20 hours/week based on performance and business needs
• Schedule: Flexible with core availability during business hours (typically Monday- Friday)
• Work arrangement: Primarily virtual with local in-person availability
• Requirements: NDA and BAA signing required

To Apply

Please submit the following to eclemensot@gmail.com or apply on Indeed:

• Resume (no more than 3 pages) highlighting relevant experience
• Cover letter (2 pages max) addressing:
• How you currently use AI tools in your work (be specific!)
• An example of a system or process you've created or improved
• Why you're interested in this particular role and what makes you a great fit
• Your availability and ideal working arrangement
• AI Tool Proficiency Statement: List the AI tools you use regularly and give one concrete example of how you've used AI to solve a problem or improve efficiency
• 3 professional references (name, relationship, contact info)

Optional but encouraged:

• Portfolio or examples of relevant work (social media content, photography, process documentation, etc.)
• Brief description of your LLC and website address (if applicable)

Subject line: EA Application - [Your Name]

Application deadline: December 19, 2025 or until filled

Job Types: Part-time, Contract

Pay: $25.00 - $40.00 per hour

Expected hours: 5 – 10 per week

Work Location: Hybrid remote in Woodbridge, VA 22192