Executive/Personal Assistant for Private Principal at Pocketbook Agency Portland, OR

Executive/Personal Assistant for Private Principal job at Pocketbook Agency. Portland, OR.

A private principal with multiple personal and business ventures is seeking a proactive and highly capable Executive/Personal Assistant to provide seamless support across both professional and household operations. The ideal candidate is thoughtful, resourceful, and able to manage a wide range of responsibilities with grace, integrity, and efficiency.

This is an excellent opportunity for a sharp, grounded professional who enjoys variety and thrives in a role where no two days are the same.

Responsibilities

• Serve as the principal’s right hand, managing scheduling, correspondence, and day-to-day priorities
• Handle personal and executive administrative needs, ensuring all details are managed with precision and care
• Coordinate vendors, household staff, and outside professionals to keep personal and property operations running smoothly
• Oversee contracts, invoices, and project timelines related to real estate and construction initiatives
• Provide light estate management support for multiple residences, including a large coastal property
• Organize personal errands, appointments, and household purchases
• Act as a trusted liaison and gatekeeper, maintaining discretion and protecting the principal’s time and interests
• Support special projects and new business ventures, including potential product and brand acquisitions
• Maintain strong communication with the principal, ensuring proactive follow-up and organization across all areas

Requirements

• 5+ years of experience as an Executive Assistant, Personal Assistant, or hybrid EA/PA in a private or entrepreneurial setting
• Outstanding organizational and communication skills; able to multitask with calm efficiency
• Strong judgment, discretion, and emotional intelligence
• Confident managing vendors, service providers, and external partners
• Experience in real estate, construction, or project management is a major plus
• Tech-savvy, reliable, and able to work both independently and collaboratively
• A natural problem solver who stays one step ahead and thrives in dynamic environments
• Loyal, honest, and grounded with a service-oriented attitude and sense of humor
• Availability for limited travel, occasional local or regional site visits

Schedule: This is a full-time role, Monday through Friday

Compensation

Up to $120K+ based on experience

Location: Portland, OR (mostly remote), limited travel