Hours: 20–30 hours week | Compensation: Hourly, DOE

We are seeking an exceptional, experienced Personal Assistant Chief of Staff to support a busy private individual and his family. This is a highly trusted, long-term partnership role that combines operational excellence, structure, accountability, and emotionally intelligent support. The ideal candidate is confident, emotionally mature, thinks three steps ahead, and is able to provide thoughtful guidance and proactive problem-solving while maintaining discretion and professionalism.

In this role, you will manage calendars and appointments across personal, family, and professional domains; create structure for goals, routines, and priorities, including check-ins and accountability support; prepare notes for meetings; track follow-ups; and ensure all tasks and processes are fully documented. You will also maintain household, family, and personal records, including medical and financial information; arrange domestic and international travel with detailed itineraries; coordinate with vendors; assist with events and lifestyle planning; and maintain databases of ideas, travel, and activities.

We are focused on finding a candidate with 5–10 years of executive or personal assistant experience who thrives on building systems, maintaining organization, and anticipating needs. High emotional intelligence, intuition, and the confidence to provide constructive pushback are also important. This role is essentially a mini chief of staff for personal life, blending operational structure with insight. Candidates should be tech-savvy, with proficiency in Google Workspace and task or project management tools, comfort learning new systems including AI tools, excellent written and verbal communication skills, strong organizational ability, high attention to detail, and the capacity to think strategically.

We would especially like to hear from you if you have experience supporting a founder or other high-autonomy individual, have managed household staff or complex family logistics, or are comfortable acting as a chief of staff for life operations, including goal-setting, accountability, and system building.

This is not a typical PA role — the right candidate will be a true partner helping our client navigate a full, dynamic life in a position that rewards initiative, discernment, and relational intelligence. If interested in this on-site part-time opportunity, please reach out with your hourly compensation request and updated resume.

Thank you!

Socialite in Bel Air is in need of an assistant to help with calendar, travel and errands. Would love the professional that has a good eye and loves design and picking things up at different designers, oversee the contractors, returns. The home that she is in will be photographed, – would love it if you love fashion and design. The nuacnes involved

claudia@thehelpcompany.com

This young very busy couple is looking for that unicorn who enjoys house management and assistant work. They enjoy their privacy, so you will be working partially remote. The couple is looking for a new home, so if you have a good black book with great plumbers, electrician, etc – that would be a plus. They travel monthly, so you will be booking travel and keeping an immaculate calendar! They do love to entertain, so it would be wonderful if you are good with events and dinner parties. This is a job for someone that has the attitude of no job is too big or too small!! One caveat is that you need to be good with someone that might change their mind a lot – they want someone kind as they love their housekeeper and want someone nice to her!
plan trips
research vacations
good calendar skills
errands
good organizational skills
understand boundaries
detail oriented
Salary DOE
claudia@thehelpcompany.com