Bolton & Associates is a dynamic entrepreneurial platform that supports a diverse portfolio of innovative businesses at the intersection of technology, real estate, AI, and professional services. We specialize in building and scaling high-growth ventures through strategic operations, management consulting, software development, intellectual property, marketing, and sales. Our mission is to drive meaningful impact through cutting-edge solutions, entrepreneurial leadership, and practical innovation. We foster a fast-paced, hands-on environment where team members gain direct exposure to real business challenges and opportunities alongside experienced leadership. This is a great place for motivated people to learn, contribute, and grow in a supportive, multi-faceted organization.

Executive & Personal Assistant (Part-Time)

Company: Bolton & Associates, LLC (Bolton AA)

Location: Hybrid / Remote (Northern Virginia preferred)

Schedule: Part-Time (20–30 hours per week, flexible)

Reports To: CEO & Founder

About Bolton & Associates

Bolton & Associates (Bolton AA) is an executive advisory and growth consulting firm that helps business owners, executives, investors, and organizations increase profitability, improve operations, adopt Artificial Intelligence, and build scalable businesses.

We believe technology should help people—not replace them. Our mission is to simplify complexity, accelerate growth, and help leaders make better decisions.

Position Overview

We are looking for an exceptionally organized, proactive, trustworthy Executive & Personal Assistant who enjoys creating order from chaos.

This is not a traditional administrative assistant role.

You will become the operational extension of the CEO, helping manage multiple companies, projects, meetings, travel, communications, AI initiatives, personal priorities, and special projects.

The right person enjoys solving problems before they become problems.

You thrive on checklists, systems, follow-up, organization, and helping leaders perform at their highest level.

Primary Responsibilities

Executive Support

• Manage executive calendar
• Coordinate meetings and appointments
• Prioritize daily activities
• Schedule travel and accommodations
• Prepare agendas and meeting materials
• Record meeting notes and action items
• Follow up on outstanding tasks
• Manage executive inbox and communications
• Screen calls and requests

Project Coordination

Help keep dozens of initiatives moving simultaneously.

Responsibilities include:

• Track project status
• Maintain project dashboards
• Coordinate with consultants and vendors
• Organize documentation
• Create SOPs
• Maintain task lists
• Ensure deadlines are met
• Follow up with accountability partners

AI & Technology Support

Assist with managing AI-enabled workflows including:

• ChatGPT
• Microsoft Copilot
• Google Gemini
• Claude
• Notion
• Google Workspace
• Microsoft 365
• CRM systems
• Automation tools

No advanced AI experience is required—but enthusiasm for learning is essential.

Personal Assistance

Provide occasional personal support including:

• Personal calendar management
• Appointment scheduling
• Event planning
• Family travel coordination
• Gift purchasing
• Reservations
• Errands (as needed)
• Household/vendor coordination
• Personal document organization

Content & Marketing Assistance

Support executive content creation by:

• Formatting LinkedIn posts
• Organizing articles
• Coordinating newsletters
• Managing speaking engagements
• Maintaining content calendars
• Organizing digital assets

Business Operations

Support daily operations including:

• Vendor coordination
• CRM updates
• File organization
• Contract administration
• Document preparation
• Expense reporting
• Research projects
• Process improvement

Ideal Candidate

You are someone who naturally says:

"I already took care of it."

instead of

"What would you like me to do?"

You anticipate needs.

You love systems.

You enjoy solving problems.

You like learning new technology.

You are comfortable working directly with entrepreneurs.

You understand confidentiality.

Required Qualifications

• 3+ years supporting executives or business owners
• Exceptional written and verbal communication
• Outstanding organizational skills
• Strong attention to detail
• Professional discretion
• Self-starter
• Excellent follow-through
• Ability to manage multiple priorities
• High level of integrity

Preferred Qualifications

Experience with:

• Microsoft Office
• Google Workspace
• ChatGPT or other AI tools
• CRM software
• Project management platforms
• Canva
• LinkedIn
• QuickBooks (basic familiarity)
• DocuSign
• Zoom
• Adobe Acrobat

Characteristics We Value

We hire for attitude as much as aptitude.

We're looking for someone who is:

• Positive
• Curious
• Resourceful
• Honest
• Loyal
• Calm under pressure
• Detail-oriented
• Professional
• Adaptable
• Tech-savvy
• Service-minded
• Growth-oriented

Success Looks Like

Within the first 90 days, you will have:

• Organized the CEO's calendar and task management system
• Reduced administrative burden significantly
• Implemented improved filing and document organization
• Helped establish repeatable operational systems
• Coordinated multiple active projects successfully
• Become a trusted extension of the executive office

Compensation

• Competitive hourly compensation based on experience
• Flexible schedule
• Hybrid/remote work options
• Opportunity for increased hours over time
• Direct mentorship from an experienced entrepreneur, executive advisor, and technology innovator
• Exposure to AI, entrepreneurship, executive strategy, business operations, and emerging technologies

Why Join Bolton AA?

This position offers a unique opportunity to work alongside a serial entrepreneur who has founded multiple companies, advised executives across numerous industries, and is actively building next-generation AI-enabled businesses.

If you enjoy continuous learning, solving meaningful problems, embracing new technology, and making a measurable impact every day, we'd love to hear from you.

This is more than an assistant role—it's an opportunity to become an indispensable partner in building innovative companies and helping leaders achieve extraordinary results.