Personal Assistant to Principal

Laurel Real Estate•Pittsburgh, PA

About The Position

We are seeking an exceptional Personal Assistant to support a high-net-worth principal with complex personal, professional, and family-office-adjacent responsibilities. This role requires uncommon judgment, discretion, and anticipatory thinking. The ideal candidate operates as a trusted proxy-managing details independently, protecting the principal's time, and preventing problems before they surface. This is not a task-execution role. It is a judgment-based, trust-based position for someone who thrives on responsibility, confidentiality, and long-term partnership.

Requirements

Experience 7+ years supporting a senior executive, principal, or HNW/UHNW individual
Experience in a family office, private equity, investment firm, or high-pressure executive environment strongly preferred
Proven track record of long-term roles built on trust and discretion
Exceptional judgment and ability to prioritize in ambiguous situations
Discretion and confidentiality at the highest level
Anticipatory mindset-acts before being asked
Strong backbone-comfortable saying "no" on behalf of the principal
Calm under pressure and unfazed by complexity or changing priorities
Detail-oriented without losing strategic perspective
Highly autonomous with minimal supervision
Flexible availability aligned with the principal's needs (not a rigid 9-to-5 role)
Comfortable blending personal and professional responsibilities seamlessly
Maintains professionalism, boundaries, and sound judgment at all times

Nice To Haves

Experience in a family office, private equity, investment firm, or high-pressure executive environment strongly preferred

Responsibilities

Serve as primary gatekeeper for the principal's time, communications, and priorities
Act as a proxy decision-maker on routine and sensitive matters, escalating only what truly requires principal involvement
Anticipate needs, risks, and opportunities without being directed
Maintain situational awareness across personal, business, and family-office matters
Own all calendar strategy, not just scheduling-optimize time, energy, and focus
Plan and manage complex domestic and international travel, including contingencies
Coordinate logistics across multiple residences, offices, and time zones
Prepare the principal thoroughly for meetings, events, and decisions
Handle highly confidential personal, financial, and legal information with absolute discretion
Interface with attorneys, CPAs, bankers, investment professionals, and household staff
Manage sensitive correspondence and communications on behalf of the principal
Maintain secure systems for records, documents, and information flow
Oversee personal appointments, family commitments, and private engagements
Coordinate with household staff, vendors, and service providers as needed
Manage personal projects and special initiatives from concept through completion
Ensure seamless execution across personal and professional domains