Chief of Staff to Entrepreneur

JRN: 2132

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 and artist. 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 Jamaica, 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 Jamaica and Los Angeles required