Chief of Staff to High-Level Entrepreneur Job at Pocketbook Agency, Los Angeles, CA

Q1NuQmdkVVByZlRBS1hja3NGa0djdHlveUE9PQ==
  • Pocketbook Agency
  • Los Angeles, CA

Job Description

We are seeking a dynamic and entrepreneurial Chief of Staff to lead operations, strategy, and team oversight for a high-end rental property and emerging consumer product brand for a high-profile entrepreneur. This position will act as the central point of coordination across all on-site staff, contractors, and brand partners, transforming creative vision into clear execution plans. The ideal candidate brings strong operational instincts, a proactive mindset, and a proven ability to manage people, property, and projects with discretion and drive.

Requirements:

  • 7-10+ years of experience in Chief of Staff, operations, or brand management roles
  • Prior experience supporting a CEO, founder, or high-profile principal with multiple ventures
  • Demonstrated success in property management, hospitality, or consumer product development
  • Strong leadership and team management capabilities
  • High emotional intelligence with excellent communication and problem-solving skills
  • Ability to travel frequently to Caribbean Islands, Los Angeles, and other properties as needed
  • Entrepreneurial mindset with exceptional organizational and follow-through skills

Responsibilities:

  • Lead all aspects of operations and staffing for a private estate and rental property
  • Manage on-site team including House Manager, Grounds Manager, and contractors
  • Maximize rental bookings when the property is unoccupied and develop long-term occupancy strategy
  • Hire and oversee a contract Brand Builder to launch consumer products (e.g., coffee, honey) under a new lifestyle brand
  • Work alongside the business manager to bring structure, timelines, and operational clarity to strategic initiatives
  • Serve as the main point of contact for property and brand-related matters, reducing the burden on the principal
  • Provide clear, thoughtful feedback and translate creative ideas into actionable plans

Schedule:

Full-time, requires schedule flexibility and frequent travel

Compensation:

$140,000 – $220,000, depending on experience

Location:

Flexible, though proximity to Los Angeles is highly preferred; heavy travel to Caribbean Islands and Los Angeles required

Job Tags

Full time, Contract work, For contractors, Flexible hours,

Similar Jobs

PwC

Oracle Cloud Finance - Senior Associate Job at PwC

 ...Transformation journey enabled by Oracle Cloud ERP and EPM. You will be part of a team that...  ...-led and values-driven leader at every level. To help us achieve this we have the PwC Professional...  ...does not intend to hire experienced or entry level job seekers who will need, now or in... 

Ohio Staffing

Patient Escort (11am - 7:30pm, Riverside) Job at Ohio Staffing

 ...inspire hope. We learn, grow, and achieve more in our careers and in our communities. Responsibilities And Duties Transports patients to and from various departments in a safe and efficient manner. (Use utility life equipment as trained.) Maintains equipment to... 

Massachusetts AGO

Assistant Attorney General | Civil Rights Division Job at Massachusetts AGO

 ...equity, underscoring the importance of intersectionality and racial justice. Embedded in the Division are units dedicated to protecting...  ..., public accommodations, employment, education, healthcare, criminal justice, immigration, and voting. Primary Duties: The Assistant... 

MV Transportation

Hiring Event August 5th - School Bus Drivers and Attendants Job at MV Transportation

 ...Applicant Privacy Policy for more information about our data handling practices and your data rights. Walk In JOB FAIR Hiring School Bus Drivers Immediately! Offering $1,000 sign on bonus to the first 12 once completing training after 90 days of service. NOW... 

Refresco

Forklift Operator- Night Shift Job at Refresco

 ...the required personal protective equipment (PPE) while in the warehouse or production areas (including but not limited to hairnets/beard...  ...directed by leadership. Clean/maintain work areas throughout the shift. Represents the company in a positive manner at all times....