Executive Assistant

Position Title : Executive Assistant

This is not a traditional administrative support role. We are seeking an experienced Executive Assistant to provide high-trust executive and operational support to the Managing Director of an ambitious, development-stage organization in the private military services industry. This individual will manage complex scheduling, executive communications, travel, briefings, stakeholder coordination, events, and critical follow-through while helping establish the systems and structure needed to support significant future growth.

The ideal candidate brings a military background, exceptional judgment, and the ability to operate calmly in a demanding, fast-moving environment where priorities can shift quickly. They are highly organized, discreet, and proactive, with the confidence to anticipate problems, coordinate across multiple stakeholders, and take ownership without waiting for constant direction.

Salary Range: $70,000–$125,000 / Year, DOE

Responsibilities

• Own the Managing Director’s complex calendar, meetings, deadlines, and competing priorities, proactively identifying conflicts and recommending solutions
• Prepare executive briefings, agendas, background research, talking points, presentations, reports, and decision-making materials
• Coordinate domestic and international travel, including transportation, accommodations, itineraries, security considerations, and contingency planning
• Serve as a trusted liaison between the Managing Director, leadership, and internal and external stakeholders, ensuring clear communication and consistent follow-through
• Track executive decisions, commitments, action items, owners, and deliverables through completion
• Plan and coordinate leadership meetings, site visits, executive events, customer engagements and formal functions with appropriate attention to logistics and protocol
• Establish and improve administrative processes, reporting systems, meeting rhythms and executive-office workflows while protecting highly sensitive business, personnel, financial and strategic information

Requirements

• 5+ years of experience in executive support, operations, project coordination, military leadership, or a comparable high-responsibility environment
• Military background required, with a strong understanding of disciplined, mission-focused and high-tempo operating environments
• Bachelor’s degree or equivalent professional experience
• Demonstrated experience supporting senior leaders while managing multiple stakeholders, priorities, and deadlines with minimal supervision
• Exceptional organization, written communication, attention to detail, discretion, and sound judgment
• Advanced proficiency with calendar, email, presentation, collaboration, and productivity tools
• Ability to work onsite and maintain flexible availability when urgent executive priorities, travel coordination or events require additional supports

Benefits

• Planned employer-paid medical, dental, and vision coverage for employees and eligible dependents
• Initial PTO offering anticipated at 10–15 total days, combining vacation and sick time
• Practical flexibility for occasional family and personal needs
• Opportunity to provide input as the organization develops its long-term employee benefits program
• Direct access to senior leadership and significant visibility across the organization
• Opportunity for responsibilities to expand as the company grows and the individual demonstrates their strengths

If you are a military professional who thrives under pressure, anticipates what leaders need before being asked, and wants to bring your discipline and operational experience into a high-impact executive support role, apply today.