Senior Executive & Personal Assistant to Private Principal

Senior Executive & Personal Assistant to Private Principal

Location: Bend/Tumalo, Oregon
Schedule: Full-time, Monday–Friday, with flexibility for travel, occasional evenings and weekends, and time-sensitive needs
Proposed compensation: $120,000–$150,000 annually, depending on experience; final compensation and benefits to be confirmed
Travel: Domestic and international travel required (Passport required)

Cassie’s Cardinals is seeking an experienced Senior Executive & Personal Assistant to support a private principal across multiple businesses, real estate investments and development projects, personal and family administration, extensive travel, and a growing fashion and creative business.

The ideal candidate has served as a trusted right hand to a senior executive or private principal. They bring excellent judgment, strong business acumen, and the ability to manage competing priorities independently while keeping the principal informed.

Responsibilities

Executive and business support

• Manage complex business and personal calendars, correspondence, meetings, and follow-ups.
• Prepare meeting materials, track action items, and ensure deadlines are met.
• Coordinate with attorneys, accountants, advisors, consultants, and contractors.
• Organize contracts, records, project timelines, and outstanding decisions across multiple ventures.
• Research options and present clear, concise recommendations.

Travel planning and support

• Arrange complex domestic and international travel, including flights, accommodations, ground transportation, reservations, and appointments.
• Build detailed itineraries and maintain travel documentation.
• Manage changes, disruptions, and last-minute requests calmly and efficiently.
• Coordinate with traveling staff, stylists, PR teams, and overseas contacts.
• Accompany the principal on domestic and international trips as needed.

Personal and family administration

• Coordinate appointments, school communications, children’s activities, family travel, and personal events.
• Manage gifting, purchases, deliveries, special orders, and returns.
• Maintain personal records, subscriptions, and administrative systems.
• Work collaboratively with household staff and service providers while respecting established responsibilities.

Fashion, creative, and brand support

• Coordinate meetings and appointments with fashion houses, stylists, PR representatives, and creative partners.
• Organize logistics for Fashion Weeks, fittings, special events, and brand appointments.
• Track shipments, purchases, returns, creative commitments, and project deadlines.
• Support administrative and logistical needs for content creation and brand partnerships.

Financial organization and systems

• Use QuickBooks to support accurate financial organization.
• Organize invoices, expenses, receipts, reimbursements, and supporting records.
• Coordinate with accountants and financial advisors.
• Maintain effective tracking systems across business and personal responsibilities.

Required Qualifications

• At least seven years of substantial Executive Assistant experience supporting a CEO, founder, entrepreneur, investor, or private principal.
• Demonstrated experience providing both executive and personal support.
• Proven experience planning complex international travel.
• Willingness and ability to accompany the principal on domestic and international trips.
• Hands-on QuickBooks proficiency.
• Strong proficiency with spreadsheets, calendars, email, and document management systems.
• Excellent written and verbal communication, discretion, emotional intelligence, and judgment.
• Ability to turn verbal instructions and voice notes into organized action items.
• Regular in-person availability in Bend/Tumalo.
• Valid driver’s license and passport, and ability to travel internationally.
• Willingness to sign a confidentiality agreement.

Experience with high-net-worth principals, private family offices, luxury services, fashion, entertainment, real estate, or development projects is strongly preferred.

Working Style

The successful candidate is proactive, resourceful, organized, and calm under pressure. They communicate concise updates, flag concerns promptly, bring possible solutions, and follow through consistently. They take initiative while recognizing which decisions require the principal’s approval.

Warmth, professionalism, attention to detail, and a collaborative approach with family members, staff, and business contacts are essential.

This position coordinates with existing household management, housekeeping, and childcare professionals.

Selection Process

Candidates should be prepared to discuss specific examples of executive support, complex travel planning, competing priorities, and independent problem-solving. The process will include interviews, a brief practical exercise, professional reference checks, and a background check before final selection.

An overlap with the outgoing assistant is planned to support a thorough transition.

Requirements

• A cover letter is REQUIRED when uploading your resume.
• Exceptionally organized and detail-oriented.
• Proactive and naturally takes initiative.
• Strong organizational skills with the ability to prioritize tasks effectively in a fast-paced environment.
• Strong written communication and clear reporting to the Office.
• Trustworthy, discreet, and accustomed to working around private residences.

Pay: $120,000.00 - $150,000.00 per year

Application Question(s):

• Please explain your experience of substantial Executive Assistant experience supporting a CEO, founder, entrepreneur, investor, or private principal.

As well as including it in your cover letter.

Experience:

• Executive Assistant supporting a CEO, founder, entrepreneur: 7 years (Required)

Ability to Relocate:

• Bend, OR 97701: Relocate before starting work (Preferred)

Work Location: In person

Salary : $120,000 - $150,000