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

djlHVlkwUlYxZzRmcnV3azdRcFRDZGt2R3c9PQ==
  • 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

Please Assist Me Inc

Household Personal Assistant. Job at Please Assist Me Inc

 ...Household Assistants Wanted Looking for an exciting and engaging part-time job? Want an opportunity to grow with a fast-growing business...  ...running miscellaneous errands like taking mail to the post office, picking up dry cleaning, shopping for groceries, and other deliveries... 

Best Value Food Products

Night Shift Warehouse Selector / Picker Job at Best Value Food Products

 ...Night Shift Selector Full Time, Come join our Team! COME JOIN OUR TEAM! Best Value Food Products, is looking for experienced, positive and energetic (Warehouse Selectors) to join our night shift team! Primary Responsibilities: The Warehouse Selector is responsible... 

Populus Denver

Lifestyle Manager Job at Populus Denver

 ...LIFESTYLE MANAGER Reports to: General Manager, position is exempt Accepting applications through February 8, 2026, or until filled WHO WE ARE Hotels done differently. At Aparium, we believe in the power of People, Place and Character. We ensure our... 

Minnesota Department of Employment and Economic Development

Employee and Labor Relations Consultant - Human Resources Consultant 1 Job at Minnesota Department of Employment and Economic Development

 ...Temporary : Unlimited Who May Apply : Open to all qualified job seekers Date Posted : 12/12/2025 Closing Date : 12/26/2025 Hiring Agency/Seniority Unit : Employment and Economic Development Department-Confidential Division/Unit : Human Resources Work... 

Maxim Healthcare Service

RN/Maxim Healthcare/ Private Duty Nursing Job at Maxim Healthcare Service

 ...Private duty nursing (PDN) allows medically fragile patients to receive quality, skilled nursing care in the comfort of their home: a setting...  ...by most patients and their families. North East 21901 LPN/RN Peds, gtube, trach, vent Every night 10p-6a or 11p-7a Additional...