Executive Assistant to Chief Executive Officer

Overview

We are seeking a highly capable Executive Assistant to support the CEO of a fast-growing real estate-focused organization with a large runway of success ahead. This role exists to maximize the effectiveness of the CEO's limited working time across multiple business lines while preserving flexibility, autonomy, and a non-reactive operating environment.

While there will be plenty of routine administrative tasks, this is not just a traditional administrative role. It is designed for someone who can operate independently, think critically, and manage execution across initiatives without constant supervision.

This is NOT a remote role. Must be able to reliably commute to Richmond, VA offices.

This role IS:

• Highly autonomous
• Structured around recurring deliverables
• Focused on leverage, not presence

This role is NOT:

• A task-by-task assistant role
• A calendar-only administrative position
• A position dependent on the CEO’s daily activity

• Manage scheduling, confirmations, rescheduling, and cancellations
• Manage emails, phone calls, and other communication
• Prepare meeting briefs and context
• Attend select meetings to capture notes and action items
• Track commitments and ensure follow-through
• Protect the CEO’s calendar from unnecessary interruptions
• Handle daily/weekly routine administrative tasks or projects across businesses
• Work closely with other team members involved across businesses

• Capture ideas and initiatives discussed by the CEO
• Translate ideas into defined next steps or research
• Coordinate follow-ups with internal and external stakeholders
• Provide concise updates for decision-making

• Research potential expansion markets and/or business opportunities
• Compile competitor and market intelligence
• Support podcast guest outreach, scheduling, and asset organization
• Assist with presentations, speaking events, or other larger business projects
• Assist with lending business administration, relationship tracking, and deal summaries
• Maintain clean pipelines of opportunities

• Handle personal administrative tasks as assigned
• Coordinate document collection and organization
• Assist with appointment scheduling and logistics

• 3+ years experience supporting executives or founders
• Exceptional organization and written communication skills
• High level of confidentiality, discretion, and professionalism
• Comfortable operating independently
• Strong judgment and attention to detail
• Calm, proactive, and low-ego working style

• Improved execution and follow-through
• Increased conversion of ideas into action
• Cleaner, more impactful working hours for the CEO
• Reduced administrative and personal-life friction

Estimated starting annual salary range of $60,000-$70,000. Ultimately, compensation will be commensurate with experience, autonomy, and scope of responsibility. Full benefits and growth opportunity available.

Qualified candidates should submit a resume. A brief cover note explaining why they are well-suited for an autonomous, outcome-driven executive support role is preferred.

• 401(k) matching
• Health insurance
• Vision insurance
• Life insurance
• Paid time off, holiday pay, sick pay
• Directly support the CEO of a winning and fast-growing team