Flagger Force Jobs in California (NOW HIRING)

Our client, a truly dynamic and mission-driven executive based in San Carlos, CA, is seeking an exceptional part-time Senior Executive Personal Assistant to serve as her right hand across both professional and personal domains. This is a role for someone who thrives on variety, moves fast, and genuinely enjoys being the steady, organized force behind a high-energy, high-capacity principal. Our client works from home, is warm and funny, deeply creative, and a direct communicator - she needs a professional who can track with her quick pace, anticipate needs before they become urgent, and reduce the mental load of constantly switching between competing priorities.

This role sits above a traditional EA, without being a full Chief of Staff. The ideal candidate is a strong thought partner: someone comfortable triaging competing priorities, flagging when details don't add up, and helping create healthy boundaries around our client's time. This is a hybrid position, with regular in-person time balanced by remote work; our client is not looking for someone on-site daily, but does want consistent, reliable touchpoints and easy access when needed.

Responsibilities

• Serve as a true thought partner and right hand across personal and professional domains
• Manage complex travel logistics, including flights, hotels, ground transportation, packing considerations based on climate/dress code, and day-of coordination
• Triage and manage email and communications, flagging what's urgent versus what can wait
• Coordinate with outside parties (attorneys, real estate agents, publishers, etc.) to keep documents and processes moving
• Support submission and tracking of professional written works
• Conduct research on request and provide clear, concise recommendations (e.g., "I looked at 10 options, here are my top 3, and here's my recommendation")
• Handle administrative loose ends that tend to fall through the cracks, such as reimbursements and unused credits
• Assist with light personal errands, returns, and day-to-day logistics as needed
• Use AI-assisted tools (including Claude) to support workflow efficiency, communication, and organization
• Proactively flag scheduling conflicts or misaligned timelines across different parties supporting our client
• Communicate clearly and consistently, ensuring nothing important is dropped or delayed

Qualifications

• A minimum of 7+ years of experience working as a Senior Executive Assistant, or similar right-hand role supporting a high-capacity principal
• Excellent judgment and the ability to work autonomously once onboarded
• Outstanding communication skills; comfortable with texts, calls, and a fast-paced, responsive communication style
• Strong technological fluency, including comfort using AI tools such as Claude to support workflow and productivity
• Highly organized, detail-oriented, and unflappable when managing multiple moving pieces at once
• A genuine thought partner who can push back thoughtfully and help protect our client's time and boundaries
• Comfortable with a hybrid schedule; flexible and reliable without needing to be on-site daily
• A good sense of humor and an easygoing, can-do personality is a big plus
• Legally authorized to work in the US
• Local to the Bay Area - within a commutable distance
• Willing to undergo an in-depth background check and provide strong employment references 

Schedule & Compensation

• Part-time, approximately 20-30 hours per week, with potential for more (including possible full-time down the road for the right fit)
• Hybrid schedule, with a mix of in-person and remote work
• $70+ per hour | depending on experience; guaranteed weekly hours

DM Estate Staffing is a domestic staffing firm headquartered in Silicon Valley, dedicated to connecting exceptional Private Service Professionals with private clients and family offices across the United States. Built over more than a decade on referrals and repeat clients, we have grown thoughtfully by doing one thing well: finding the right person for the right home.

Every member of our recruiting team has worked personally in the homes of prominent private clients, as estate managers, private chefs, household leaders, and more. That lived experience is what sets us apart. We don't just understand private service in theory; we've navigated its nuances, its demands, and its deeply personal nature from the inside. That perspective shapes every search we conduct and every candidate we represent.

We encourage you to regularly explore our job board and apply for any roles that align with your experience and aspirations. When your background aligns with what our clients are looking for, we will be in touch. We hope to have the opportunity to work with you soon.