Chief of Staff to Entrepreneur Job at Pocketbook Agency, Ventura County, CA

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  • Pocketbook Agency
  • Ventura County, CA

Job Description

A dynamic entrepreneur based in Ventura/Santa Barbara is seeking a highly capable and driven Chief of Staff to serve as their right hand across personal, professional, and creative ventures. This is a unique opportunity for someone who thrives in a fast-paced, ever-evolving environment, is energized by solving complex problems, and wants to grow alongside an ambitious founder.

Key Responsibilities:

Executive Support

  • Proactive calendar and schedule management across multiple time zones
  • End-to-end travel planning and logistics (domestic/international, personal/professional)
  • Handle speaking engagements, podcast appearances, and related coordination

Family + Household Support

  • Liaise with nanny to ensure seamless coordination for the children
  • Oversee grocery deliveries, school schedules, and extracurricular logistics
  • Manage gifting for family and friends, including holidays, birthdays, and special occasions

Business & Venture Support

  • Provide hands-on support in launching and building new ventures
  • Be a thought partner and sounding board for ideation, strategy, and execution
  • Support photography and creative production logistics

Operations & Relationship Management

  • Serve as the point of contact for the family office and financial team
  • Manage incoming requests from extended family and friends (reimbursements, travel, etc.)
  • Coordinate philanthropic efforts and charitable initiatives
  • Onboard and manage social media consultants and platforms

IT + Property Oversight

  • Troubleshoot and coordinate IT needs across personal and professional devices
  • Oversee multiple properties, including a home in Costa Rica, ensuring maintenance and operations run smoothly

Ideal Candidate:

  • Prior Chief of Staff or Senior Personal Executive Assistant experience supporting a founder or CEO
  • Naturally strategic, organized, and solutions-oriented
  • Able to handle a 24/7 mindset and thrive in a role that touches every part of a busy, multifaceted life
  • Comfortable balancing high-level strategy with day-to-day execution
  • Excellent communication skills with high emotional intelligence and discretion
  • Tech-savvy, detail-oriented, and energized by supporting ambitious goals
  • Creative, resourceful, and excited to learn from and grow alongside an entrepreneur

Salary: $150,000-$175,000

Benefits: Unlimited PTO, Phone stipend, Health care stipend, Bonus

Job Tags

Holiday work,

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