Executive Assistant / Office Administrator

Blue Box Auction Gallery is seeking a highly capable, discreet, and proactive Executive Assistant / Office Administrator to serve as a behind-the-scenes partner supporting the founder and key leadership of a growing, entrepreneurial organization.

This is not a task-only administrative role. This position is for someone who understands how entrepreneurs operate, can anticipate needs, recommend actions, and reliably handle follow-through with professionalism and discretion.

About the Role

This is a part-time, flexible Executive Assistant / Office Administrator role (approximately 10-20 hours per week) with the opportunity to likely grow in responsibility and scope over time as trust and familiarity develop. A full-time role will likely be available within 6-12 months.

You will work closely with the founder and support both personal executive priorities and business operations, including financial administration, scheduling, communications, and systems improvement.

The role is remote, but the candidate must be local to the Hampton Roads / Virginia Beach area for occasional in-office meetings.

What You Will Do

Executive & Administrative Support

• Manage complex calendars, scheduling, and coordination across multiple stakeholders and business interests
• Coordinate meetings, calls, events, and occasional travel
• Draft, review, and manage professional communications on behalf of leadership
• Serve as a trusted point of contact with clients, vendors, and partners
• Anticipate needs in a fast-moving, high-context environment

Bookkeeping & Financial Administration

• Perform reconciliations, invoicing, and bill payments
• Assist with auction settlements and financial documentation
• Prepare financial summaries and reports for leadership
• Work within QuickBooks and coordinate with outside accounting support as needed
• Handle sensitive financial and business information with absolute confidentiality

Operations & Systems

• Improve internal systems and workflows
• Document processes and create operational clarity
• Utilize technology and tools to streamline day-to-day operations
• Support CRM usage and data organization
• Identify inefficiencies and recommend practical solutions

Who This Role Is For

You are likely a strong fit if you:

• Have experience as an Executive Assistant or senior administrative professional
• Thrive supporting entrepreneurs or business executives
• Are comfortable operating with incomplete information and moving quickly
• Can prioritize, recommend actions, and execute independently
• Are highly organized, detail-oriented, and reliable
• Communicate clearly, professionally, and confidently
• Value discretion, integrity, and trust above all else

This role is ideal for someone who is:

• Highly skilled and polished looking for meaningful part-time work
• Not seeking (or able to commit to) a full-time role
• Interested in a long-term, evolving professional partnership

Required Skills & Experience

• Strong proficiency with QuickBooks
• High level of comfort with Microsoft Office, Teams, CRM systems, and digital workflows
• Experience handling confidential and sensitive information
• Excellent written and verbal communication skills
• Ability to manage multiple priorities with minimal supervision

Experience in auctions, art, collectibles, or luxury markets is a plus, but not required. Understanding the mindset and pace of an entrepreneur is essential.

What Matters Most

• Discretion and confidentiality
• Honesty, integrity, and follow-through
• Proactive problem-solving
• Calm, capable presence in a fast-moving environment
• Professionalism in all external communications

Compensation & Structure

• Part-time, flexible schedule (approximately 5–10 hours per week)
• Hourly compensation based on experience
• Open to contractor or employee structure
• Opportunity for expanded hours, responsibility, and long-term growth

This Role Is Not a Fit If You:

• Prefer rigid structure or close supervision
• Are uncomfortable with ambiguity or shifting priorities
• Have limited experience supporting executives or entrepreneurs
• Have left prior roles on poor terms or lack strong professional references

Why Blue Box Auction Gallery

• Exposure to high-value assets and sophisticated clients
• A growing business with evolving opportunities
• A leadership team that values trust, competence, and initiative
• An opportunity to become a true behind-the-scenes partner, not just support staff

How to Apply

If you are interested in a trusted, flexible Executive Assistant role and believe your experience aligns with the expectations above, we encourage you to reach out to begin a conversation.

Job Types: Part-time, Contract

Pay: From $20.00 per hour

Application Question(s):

• What spoke to you about this opportunity and why would you be a good fit for the role?
• What areas in the description will you excel with the most and why?
• The expectation is you'll learn the new industry and be willing to learn/improve skills. With that in mind, what areas in the description will you struggle with the most?
• Explain your availability and how a part-time role will fit into that schedule? Will that schedule change in the future and how? Are you open to full-time in the future?

Work Location: In person

Salary : $20