CHIEF OF STAFF / EXECUTIVE PERSONAL ASSISTANT FOR UHNW BUSINESS OWNER – METRO PITTSBURGH, PA

CHIEF OF STAFF / EXECUTIVE PERSONAL ASSISTANT FOR UHNW BUSINESS OWNER – METRO PITTSBURGH, PA

Our client, a UHNW business owner based in Metro Pittsburgh, PA, is seeking an experienced Chief of Staff to become the principal's trusted right hand and strategic partner, supporting both their professional and personal world.

As the demands of the business, household, and personal responsibilities continue to grow, they are looking for someone who can step in, create organization, anticipate needs, and provide seamless support across every aspect of their world.

The successful candidate will become the principal's trusted right hand, overseeing everything from executive support and strategic initiatives to household operations, travel, vendors, and special projects, making sure nothing falls through the cracks. The ideal person is naturally proactive, enjoys staying several steps ahead, and takes pride in solving problems before they ever reach the principal.

They are calm under pressure, exceptionally organized, emotionally intelligent, and comfortable managing multiple priorities while exercising excellent judgment and complete discretion. Above all, they are looking to build a long-term partnership with a principal who values trust, loyalty, and professionalism.

This is an outstanding opportunity for an experienced Chief of Staff who enjoys wearing many hats and thrives in a fast-paced, ever-changing environment. The successful candidate will become an integral member of the principal's inner circle and play a key role in helping both the business and household operate at the highest level

Responsibilities

Executive and Strategic Support

• Serve as the primary point of contact and trusted advisor to the principal across professional and personal matters
• Manage an exceptionally complex calendar, balancing business, personal, philanthropic, and board commitments
• Prepare meeting agendas, executive briefings, talking points, reports, and presentation materials
• Attend meetings as requested, document key decisions, track action items, and ensure timely follow-up
• Draft and manage confidential correspondence on behalf of the principal
• Filter information, prioritize competing demands, and ensure the principal remains focused on high-value decisions
• Manage sensitive and highly confidential information with absolute discretion
• Anticipate scheduling conflicts and proactively develop solutions before issues arise

Chief of Staff and Project Management

• Coordinate communication across business, legal, financial, philanthropic, and household teams
• Lead strategic initiatives and special projects from concept through completion
• Monitor deadlines, priorities, and organizational initiatives while proactively identifying and resolving issues
• Liaise with attorneys, financial advisors, executives, consultants, and other key stakeholders
• Develop systems and processes that improve organization, communication, and operational efficiency

Executive Personal Assistant and Lifestyle Management

• Coordinate complex domestic and international travel, including private aviation, accommodations, ground transportation, and detailed itineraries
• Oversee multiple residences while coordinating with household staff, property managers, vendors, and contractors
• Manage personal appointments, family logistics, medical scheduling, gift purchasing, and special events
• Coordinate VIP guests and personal hospitality
• Support personal projects while maintaining complete confidentiality

Household and Staff Management

• Provide leadership and oversight to household staff and external service providers across multiple properties
• Recruit, onboard, supervise, and evaluate household personnel as needed
• Oversee household operations, budgets, vendor relationships, contracts, and ongoing property projects
• Develop and maintain operating procedures to ensure consistency and exceptional service standards

Financial and Administrative Support

• Review and approve invoices, expense reports, budgets, and household expenditures
• Coordinate with family office, accounting, legal, and wealth management professionals
• Maintain contracts, NDAs, vendor agreements, and confidential documentation
• Assist with legal correspondence and document review as requested

Qualifications

• Minimum of 10 years supporting a UHNW entrepreneur, founder, executive, family office, or private principal
• Previous experience as a Chief of Staff, Executive Personal Assistant, Senior Executive Assistant, Family Office professional, or similar leadership role
• Proven ability to manage multiple high-priority projects simultaneously
• Experience supervising staff, vendors, and household operations
• Strong financial acumen and experience managing budgets and confidential financial information
• Outstanding written and verbal communication skills
• Exceptional organizational and project management abilities
• Technology savvy with advanced proficiency in Microsoft Office and digital productivity tools
• Ability to travel domestically and internationally as required
• Bachelor's degree required; advanced degree preferred
• Willingness to execute a comprehensive confidentiality agreement

Location: Metro Pittsburgh, Pennsylvania

Schedule

• Full-time
• Primarily based in Farmington, PA
• Travel required as needed
• Flexibility outside traditional business hours when business needs require

Compensation and Benefits

• Approximately $200,000+ annually (DOE)
• Comprehensive benefits package to be discussed. Relocation and housing may be provided

Employment is contingent upon a clear background check and verification of professional employer references