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Personal Assistant to Chief Executive Officer

Job in Big Sky, Gallatin County, Montana, 59716, USA
Listing for: Insight Global
Full Time position
Listed on 2026-04-20
Job specializations:
  • Administrative/Clerical
    Virtual Assistant/ Remote Admin, Office Administrator/ Coordinator, Administrative Management, Business Administration
Salary/Wage Range or Industry Benchmark: 150000 - 200000 USD Yearly USD 150000.00 200000.00 YEAR
Job Description & How to Apply Below
Location: Big Sky

A client of Insight Global is seeking a Personal Assistant that provides high-level executive and personal support to a CEO across both professional and household domains. The position is best suited to a polished, service-minded professional who exercises excellent judgment, maintains strict confidentiality, and thrives in a fast-paced, high-expectation environment. The ideal candidate is a proactive problem-solver who anticipates needs, manages complex priorities with ease, and brings exceptional organization, communication, and professionalism to every interaction.

Day-to-Day

Responsibilities
  • Executive Support
  • Provide direct, high-level administrative support to the CEO, with occasional support to other members of the executive leadership team.
  • Manage complex, multilayered calendars with frequent changes, competing priorities, and regular travel.
  • Prepare, edit, and refine correspondence, presentations, reports, and other documents with a high degree of accuracy and polish.
  • Screen, prioritize, and route emails, calls, and other communications on behalf of the CEO, ensuring timely follow-up.
  • Coordinate domestic and international travel, including detailed itineraries, reservations, and logistics.
  • Support participation in industry conferences, speaking engagements, and other strategic events.
Personal and Household Support
  • Handle personal errands, appointments, reservations, and general lifestyle coordination.
  • Integrate and manage the CEO’s personal calendar in alignment with professional commitments.
  • Partner with household staff to ensure cohesive coordination of schedules and responsibilities.
  • Coordinate special occasions, personal travel, family calendars, and gifting.
  • Act as a trusted liaison on sensitive personal matters requiring discretion.
  • Assist with household vendor coordination, scheduling, and oversight as needed.
Event and Project Support
  • Support planning and execution of high-profile events, including logistics, vendor management, and on-site coordination.
  • Assist with corporate functions, client engagements, and team-building activities.
  • Conduct research and handle special projects that span both business and personal priorities.
  • Maintain organized digital and physical filing systems for personal and corporate records.
Communication and Liaison
  • Represent the CEO with professionalism, tact, and polish in all internal and external interactions.
  • Serve as a primary point of contact between the executive office and key stakeholders.
  • Maintain awareness of ongoing priorities and ensure seamless coordination across all areas of responsibility.
Required Qualifications
  • 5+ years of experience as an Executive Assistant, Personal Assistant, Chief of Staff assistant, or in a high-level service or hospitality role.
  • Proven experience managing complex, high-volume calendars and schedules.
  • Advanced proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint).
  • Outstanding written and verbal communication skills.
  • Exceptional organization, prioritization, and problem-solving abilities.
  • Professional, polished, and composed demeanor in all situations.
  • Valid driver’s license and reliable transportation for local errands and travel.
  • Ability to work flexible hours, including evenings and weekends as needed.
  • Demonstrated discretion, confidentiality, and sound judgment.
Preferred Qualifications
  • Experience in real estate, luxury services, or high-growth entrepreneurial environments.
  • Event planning and/or event logistics experience.
  • Travel coordination and itinerary management experience.
  • Familiarity with project management tools, CRM systems, or executive productivity platforms.
  • Professional excellence:
    Represents the CEO and executive team with the highest level of professionalism, judgment, and discretion across all matters.
  • Technological savvy:
    Quickly learns new systems and uses digital tools to improve efficiency, accuracy, and organization.
  • Communication mastery:
    Communicates clearly, confidently, and appropriately in both written and verbal formats.
  • Dynamic adaptability:
    Thrives in a fast-moving environment where priorities shift quickly and flexibility is essential.
  • Detail-oriented reliability:
    Maintains meticulous attention to detail while managing multiple, time-sensitive priorities.
  • Service-minded approach:
    Demonstrates a proactive, anticipatory mindset and a positive, solutions-focused attitude.
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