What are the responsibilities and job description for the Executive Personal Assistant position at The Grapevine Agency?
Executive/Personal Assistant to High-Profile CEO
Stamford, CT — Full-Time, On-Site MUST LIVE LOCAL OR RELOCATE
Schedule:
Monday–Friday, approximately 9:00 AM – 6:00 PM, with reasonable flexibility for occasional early evenings or weekend needs.
Always guaranteed two consecutive days off each week.
Compensation & Benefits:
Competitive base salary $175K DOE annual bonus
Full benefits, including 100% employer-covered health insurance, 401(k), and use of a company car (including gas)
Standard vacation: Two weeks, increasing with tenure
Relocation support short trial period with temporary housing provided
We are seeking a polished, dedicated, and professional Executive/Personal Assistant to support a charismatic and well-respected CEO whose ventures span private equity, entertainment, sports, production, and media. This is a unique chance to join a warm, collaborative team that values loyalty, kindness, and a steady, organized presence. The environment is fast-paced when needed, but the culture is healthy, respectful, and committed to reasonable work-life balance.
The CEO has partnered with the same trusted assistant for nearly a decade and is now looking for their next long-term right hand—someone grounded, reliable, and committed to maintaining a calm, seamless flow to both business and personal matters.
Key Responsibilities
Manage and maintain a dynamic calendar, partnering closely with the office administrative team to ensure smooth prioritization of meetings, appointments, and personal commitments.
Prepare and circulate daily schedules, meeting materials, and agendas.
Coordinate all personal and business travel, including private flights, luxury hotels, and well-organized door-to-door itineraries across time zones.
Track and reconcile household, travel, and personal expenses.
Schedule and oversee all personal, medical, wellness, and fitness appointments.
Assist with wardrobe organization and packing/unpacking for trips.
Print, organize, and prepare documents; accompany the principal to select meetings to provide support, take notes, and track follow-ups.
Help coordinate small dinners, gatherings, and occasional special events.
Understand the nuances of high-profile environments and support discreet entry/exit, glam moments, and light production-style needs when required.
Run errands, manage gifting, and assist with key family tasks when appropriate.
Serve as a liaison with household staff, drivers, security, and vendors to ensure smooth day-to-day operations.
Maintain a well-organized VIP contact database and update information as needed.
Manage the principal’s tech needs: phones, laptops, iPads, basic troubleshooting, and content management.
Communicate warmly, graciously, and professionally with all internal teams and external partners.
Qualifications
7–10 years as a Personal Assistant to a high-profile or UHNW individual.
Demonstrated long-term loyalty and commitment in previous roles.
Experience in entertainment, media, or supporting public-facing figures strongly preferred.
Strong ability to stay organized, anticipate needs, and pivot calmly when schedules shift.
Excellent written and verbal communication skills.
Experience in complex travel planning, personal and household support, and event coordination.
Discreet, polished, collaborative, and service-oriented, with no ego.
Must be fully comfortable with background checks and have an excellent driving record.
Willingness to travel as needed.
Salary : $175,000
