Personal Assistant to Chief Executive Officer

Insight Global; Big Sky (MT); On-site; USD 50,000 - 70,000; Full time

Job summary

A leading staffing agency is seeking a polished Personal Assistant in Big Sky, Montana, to provide extensive support to a CEO. The role demands strong organizational and communication skills, with responsibility for managing complex schedules, coordinating travel, and handling personal errands. Ideal candidates will possess over five years of relevant experience and a proactive, service-minded approach. This full-time position offers significant influence in a fast-paced environment, requiring discretion and professionalism in all matters.

Qualifications

• 5+ years of experience in a high-level assistant role.
• Proven ability to manage complex calendars and schedules.
• Advanced proficiency in Outlook, Word, Excel, and PowerPoint.

Responsibilities

• Provide high-level support to the CEO, managing their professional and personal calendars.
• Coordinate travel logistics and handle personal errands.
• Represent the CEO with professionalism in all interactions.

Skills

Executive Assistant experience

Communication skills

Organization skills

Problem-solving skills

Tools

Microsoft Office Suite

Job description

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.