Executive Personal Assistant to Private Principal

#2536

A private principal with a portfolio of residential and mixed-use properties across the PA/Jersey area and Ireland is seeking an experienced Executive Personal Assistant to bring order and structure to growing operations.

This is a build-from-scratch role for a smart, self-directed professional who is comfortable with ambiguity, can establish systems where none exist, and can serve as the principal's right hand across all matters. The portfolio spans properties, including residential homes and mixed-use commercial buildings, as well as a long-term development project on Ireland's west coast. The ideal candidate is systems-minded, communicates directly and honestly, and can set healthy boundaries while keeping operations running smoothly.

This role will be hybrid, with more in face-time to in the first month or two, but transitioning to remote first as rapport builds. You will also be flexible with short and extended travel to Ireland.

If you’re looking to join a kind and creative principal at the foundational stages of building a small, but meaningful team, this is the perfect opportunity!

Key Responsibilities

• Act as the gatekeeper to the principal, protecting their time and best interests, and acting as their proxy to make decisions and manage relationships on their behalf
• Triage and manage a significant email backlog, then build a sustainable communication system going forward
• Serve as the primary point of contact for tenants, contractors, and vendors across all properties
• Provide calendar, scheduling and travel coordination support as needed
• Research, vet, and hire property management companies and vendors for the US and Ireland operations
• Establish rent collection and tenant relationship management systems where none currently exist
• Support the review and organization of legal documents and coordinate with legal counsel
• Work closely with advisors and any business-associates to ensure seamless operational support
• Help build and coordinate teams supporting both US and Ireland operations
• Oversee day-to-day property and operational needs, resolving issues independently
• Coordinate travel and support the principal's development plans for the Ireland properties
• Assist with any other special projects

Qualifications

• Experienced professional with a background in executive assistance, estate or property management, or corporate operations
• Comfortable with ambiguity and skilled at building systems and processes from scratch
• Self directed and works well independently with little supervision and directed Self-starter with high agency who can figure things out independently
• Strong organizational skills with the ability to balance administrative work and strategic thinking
• Direct, honest communicator who can set boundaries and stay composed in complex situations
• Tech-savvy with common business and productivity tools
• Comfortable managing tenants, contractors, and vendors
• Experience dealing with any type of property management or real estate portfolio is a big plus
• Dog-friendly, as the principal has two dogs, one requiring close supervision
• Valid driver's license and reliable vehicle
• Willing and able to travel to Ireland as needed. EU or Irish work authorization is a plus for the Ireland development work

Location: Greater Philadelphia Area - Candidates can reside between New York / New Jersey and Philadelphia as long as they are willing to commute to the principal and properties up to a few times per week

Compensation: 125-170K DOE + benefits + PTO

Schedule : Initially hybrid with a fair amount of remote work as time moves forward, ability to travel to Ireland as needed

Pocketbook Agency is acting solely as a recruiting and placement firm for this position and is not the employer of record for this role unless otherwise explicitly stated. All hiring decisions, compensation, benefits, and employment terms are determined by the client employer. By applying, you acknowledge that submission of an application does not guarantee placement or employment.

Pocketbook Agency is an equal opportunity recruiting firm and does not discriminate in its recruiting, screening, or placement practices based on race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.