Santa Barbara Montecito plus Los Angeles | 20–21 Hours Week | Long-Term Growth Potential
A very special client is seeking a seasoned, highly capable, and flexible Executive to Personal Assistant to support their older, high-profile father. Although his active career is behind him, his executive and personal support needs certainly are not.

This is not an everyday role—and this is not an everyday client.
Our client is an accomplished gentleman who has had an extraordinary career and is now transitioning into a new chapter of life. He currently divides his time between Los Angeles and Montana and has recently purchased property in Montecito, which will become his primary residence once construction is completed in late 2027.
For now, this position will be approximately 80% remote and 20% in person, with the Assistant ideally based in the Santa Barbara Montecito area. When the principal is in Los Angeles, flexibility to commute to LA approximately once or twice per week will be necessary.

Initially, the position will be approximately 20–21 hours per week, Monday, Wednesday, and Friday, 7 hours per day. The role has the potential to grow significantly as the principal transitions full-time to Montecito.
A focused weekly meeting with the principal will be an important part of the position. He works best in concentrated 2–3 hour windows, so the Assistant must arrive prepared with priorities, decisions, deadlines, and action items clearly organized.

This person will become a trusted right hand, helping organize and oversee the many moving pieces of the principal’s personal, financial, household, and executive life. Responsibilities will include:
Managing calendars, appointments, meetings, deadlines, and weekly priorities
Coordinating with the family office, children, CPAs, attorneys, financial advisors, medical providers, and other professionals.

Organizing email, incoming mail, passwords, online accounts, and physical digital filing systems
Partnering with the family office and CPAs on bill pay, tax documents, insurance, financial reporting, wire approvals, and document management
Tracking important legal and estate-planning matters, including IP, estate plan, and will-related deadlines
Managing insurance providers and claims
Scheduling medical appointments and coordinating in-home care providers when needed
Coordinating vehicle maintenance and transportation
Arranging travel, primarily driving with occasional private or commercial aviation
Handling personal errands, shopping, meal ordering, dry cleaning, gifts, and other lifestyle needs
Managing credit card points and rewards
Hiring and coordinating a rental management company for the Playa del Rey residence
Maintaining organized records for homes, insurance, financial matters, and other important documents
Supporting online privacy and security, including 1Password and personal accounts

Once the principal relocates to Montecito, this position will naturally become more hands-on and may evolve into a full-time Executive Personal Assistant and trusted companion role.
We are especially interested in someone who already has strong resources and relationships throughout Santa Barbara and Montecito and can eventually assist with staffing the new residence, sourcing vendors, managing household needs, and helping the principal become established in the community.

The ideal candidate is mature, kind, patient, discreet, resourceful, and senior-level. You are exceptionally organized, know how to prioritize competing demands, and are comfortable communicating frequently with family members and a sophisticated family office.
Our client has spent much of his life steering the ship, and transitioning away from that role will require someone with a very particular touch. We are looking for a gentle but firm set of hands—someone who can respect his independence while quietly keeping things organized, moving forward, and under control.
Excellent judgment, emotional intelligence, discretion, patience, and follow-through are essential.
This is a wonderful opportunity for someone looking to build a meaningful, long-term position with a truly unique principal and family. DOE on Payroll and Benefits
Please apply to caitlin@thehelpcompany.com.

A private household in Montecito is hoping to find a highly organized, detail-oriented House Assistant to support the Family, Operations Partner, and broader Estate Team. This is a hands-on role for a proactive, roll-up-your-sleeves person with a true “no task too small” attitude. The ideal candidate is discreet, emotionally intelligent, highly organized, detail-oriented, and able to anticipate needs and thrive in a dynamic environment.

Responsibilities include local errands and deliveries, mail and package management, vehicle care, household and personal shopping, inventory management, storage and office organization, packing and travel support, pet care, event and hospitality assistance, and general estate and family support. The role requires someone who takes pride in keeping things organized, aesthetically pleasing, and running smoothly.

Candidates should have at least one year of support experience, a valid driver’s license and clean driving record, excellent communication and follow-through, and fabulous references. Hospitality, events, gifting, or high-touch service experience is a plus. Flexibility to occasionally work evenings, weekends, holidays, or overnights is required.

The standard schedule is Monday–Friday, 8:00 AM–5:00 PM, with flexibility as needed. Compensation is $60,000–$80,000 depending on experience, plus performance-based bonus eligibility, medical, dental and vision insurance, paid time off, paid holidays, and professional development opportunities.

Let us know if this role is right for you!

We are helping our Cleveland, Ohio client find an excellent executive personal assistant. He is a busy CEO that recently had some health issues arise, so he is looking for someone who can help manage both aspects of his life. Please see below for the job description from the client:

ESSENTIAL DUTIES AND RESPONSIBILITIES:
• Schedule and manage the calendar for conferences, depositions, trials and travel arrangements.
• Occasional travel with CEO.
• Manage email communications and maintain organized digital and paper files, while occasionally drafting, proofreading, editing, and organizing correspondence, reports, and other documents
• Assist with the purchase of necessary office and home supplies, within the limits prescribed
• Communicate professionally with attorneys, business associates, healthcare providers, and other contacts
• Track deadlines, prioritize tasks, and anticipate needs
• Integrating work calendar with personal calendar to ensure no overlap between appointments

PERSONAL CARE RESPONSIBILITIES:
• Assist with morning or evening routines, including showering, dressing, hygiene, and grooming (these tasks may be delegated to a special a.m. and p.m. caregiver. The decision-making is in process and is something that can be discussed.)
• Provide transfer and mobility assistance as needed during day
• Help ensure a safe and comfortable home environment
• Offer companionship while supporting independence
• Assist with light housekeeping, food prep, and other tasks related to the client’s care
• Assist as needed with at-home physical and occupational therapy
• Provide transportation with client’s vehicle to different appointments, meetings, errands, etc.
• Accompany clent to corporate headquarters nearby

KNOWLEDGE, SKILLS, AND ABILITIES:
• Knowledge of office management systems and procedures.
• MS office (Excel, Word, PowerPoint, Outlook)
• Outstanding organizational and time management skills
• Ability to multi-task and prioritize daily workload
• Excellent verbal and written communication skills
• Ability to travel via private or public transportation, with occasional overnight or multi-night stays
• Understanding of decorum, appropriate dress and presentation skills
• Ability to interact with all levels of clients, professionals such as doctors and attorneys with suitable competence

Send us your resume along with your hourly requirement if this is the perfect job for you! heather@thehelpcompany.com