Executive Assistant

Boutique Recruiting; Waynesville (MO); On-site; USD 70,000 - 125,000; Full time

Benefits offered by this job

Employer-paid medical/dental/vision

10–15 days PTO

Flexible personal needs accommodations

Input on benefits program

Access to senior leadership

Growth opportunities

Job summary

Boutique Recruiting seeks an experienced Executive Assistant to provide high-trust executive and operational support to the Managing Director in a development-stage private military services organization. This role will manage complex scheduling, travel, briefings, and stakeholder coordination, and help establish systems for future growth.

The ideal candidate has a military background, exceptional judgment, and can stay calm in a fast-moving environment where priorities shift quickly.

Qualifications

• 5+ years of experience in executive support, operations, project coordination, military leadership, or a comparable high-responsibility environment.

Responsibilities

• Own the Managing Director’s complex calendar, meetings, deadlines, and competing priorities, proactively identifying conflicts and recommending solutions

Skills

Executive support

Military background

Discretion

Judgment

Calendar management

Communication

Education

Bachelor’s degree or equivalent

Tools

Calendar software

Email tools

Presentation software

Collaboration tools

Productivity suites

Job description

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,