Chief of Staff

Bespoke Private Service

Job Description

Mowgli - Chief of Staff

Reports To : The Principals / Family Office Executive

Work Schedule : Full-Time, On-Site with regular travel to Tahoe properties (monthly/bi-monthly), Travel to remote family properties is a core operational requirement

Location : San Francisco, CA

Start Date: ASAP

Salary Range: $300,000 - $375,000

Overview

A distinguished San Francisco-based family office seeks an exceptional Chief of Staff to oversee comprehensive household operations and manage multiple properties. This strategic role supports a Principal with significant community leadership responsibilities, enabling the principal to focus on family time, creative pursuits, and personal interests while maintaining the highest standards of discretion and professionalism.

The successful candidate will be the operational cornerstone of the family's daily life, managing complex logistics across multiple residences with minimal involvement from the Principal. This role requires exceptional organizational skills, proficiency in technology, and the ability to anticipate needs proactively, ensuring seamless coordination of household management, staff supervision, property maintenance, and administrative functions. The position demands someone who understands the delicate balance of being present without being intrusive, providing five-star service with an informal, warm approach that respects the family's privacy.

We seek a detail-oriented professional who thrives behind the scenes, demonstrating emotional intelligence, strong problem-solving abilities, and a service-oriented mindset. The ideal candidate values kindness, empathy, integrity, and trustworthiness while working independently and maintaining clear communication channels. Experience in elevated environments and comfort with varied responsibilities across multiple properties is essential.

This opportunity offers the chance to make a meaningful impact on a family's quality of life while working in an environment that prioritizes work-life balance, authentic relationships, and the philosophy that life should be fully lived rather than spent managing logistics. The role is perfect for someone who believes in creating stress-free environments that allow principals to focus on what truly matters.

Expectations

• Minimum ten years of progressive leadership experience in estate management, luxury hospitality operations, or private family office environments with demonstrated success managing sophisticated multi-property operations and diverse staff teams.
• Proven expertise in high-end property management, vendor relationship development, and complex logistical coordination with a strong background in establishing operational protocols and maintaining properties to impeccable standards.
• Demonstrated expertise in organizational design and talent acquisition with proven ability to build high-performing teams through strategic hiring, comprehensive training programs, and performance management systems
• Exceptional diplomatic communication skills with the ability to lead diverse teams while maintaining harmonious working relationships and fostering a positive, collaborative work environment aligned with family values.
• Advanced proficiency in digital project management platforms, particularly Trello, Google Workspace, and secure communication tools like Signal, with a tech-forward approach to implementing efficient, user-friendly systems.
• Solid financial acumen with experience overseeing household budgets, contract negotiations, and expense management while identifying cost-optimization opportunities and maintaining service excellence.
• High emotional intelligence with exceptional discretion and confidentiality standards, adaptable professional who thrives in dynamic environments while maintaining meticulous attention to detail and a solutions-oriented mindset.
• A comprehensive understanding of security protocols and digital privacy measures is crucial for protecting high-profile individuals and families. Experience implementing robust confidentiality procedures and secure communication systems is also essential.
• Experience working effectively within family environments with an understanding of children's needs and household dynamics, and the ability to maintain warm relationships while establishing appropriate professional boundaries.
• Detail-oriented approach with meticulous project management capabilities and commitment to delivering consistent, high-quality results while operating with minimal supervision and anticipating needs independently.
• Ability to travel to family properties in the Tahoe region monthly or bi-monthly for vendor coordination, property oversight, and service standard maintenance across all locations
• Required consistent in-person presence at the primary San Francisco residence for household operations, staff supervision, and immediate response to family needs
• Experience coordinating sophisticated domestic and international travel arrangements, including advance preparation, vendor coordination, and staff travel management for major family trips

Responsibilities

• Principal Support : Create a seamless environment that enables the Principal to focus on family priorities, creative endeavors, and personal interests. Proactively anticipate needs and manage operational matters independently, ensuring minimal disruption to the Principal's time and energy while maintaining exceptional service standards.
• Multi-Property Oversight : Maintain multiple San Francisco-area residences and Tahoe properties to impeccable standards, ensuring each property remains guest-ready. Develop comprehensive property documentation, including operational manuals, maintenance protocols, and inventory management systems. Coordinate guest amenities and ensure properties are appropriately provisioned for various occasions.
• Strategic Team Leadership : Lead comprehensive team development initiatives, including workforce planning, compensation structuring, and succession planning. Oversee recruitment processes, candidate evaluations, and onboarding programs for household staff positions. Establish performance management systems and professional development pathways
• Technology Integration & Systems Management : Deploy and maintain sophisticated digital solutions for task coordination, scheduling, and project oversight. Design efficient operational systems that provide transparency and accountability without requiring Principal engagement. Ensure all technology platforms are optimized for mobile accessibility and user-friendly operation.
• Strategic Project Coordination : Direct diverse household initiatives ranging from routine maintenance to specialized projects. Monitor progress, identify potential challenges, and develop scalable solutions that can be effectively delegated while maintaining quality standards.
• Confidentiality & Security Management : Uphold the highest standards of discretion in all professional interactions. Implement comprehensive security measures for both physical properties and digital assets, including secure communication protocols and robust password management systems.
• Communications Hub : Function as the primary liaison for all household matters, filtering information appropriately and escalating only critical issues requiring Principal attention. Maintain clear, transparent communication regarding ongoing initiatives and strategic priorities.
• Executive Travel Support: Provide comprehensive coordination for major family trips, including advance preparation, logistics management, and potential travel accompaniment while managing staff travel requirements and vendor relationships

Benefits

• Comprehensive Healthcare Coverage : 100% employer-paid health, dental, and vision insurance
• Retirement Planning : 401(k)
• Performance Recognition : Performance-based annual bonus
• Compensation Growth : Annual pay increase of CPI + 1%
• Time Off: Paid time off and holidays
• Professional Growth : Professional development opportunities
• Benefits Infrastructure Development : As the inaugural team member, you'll have the opportunity to provide input on payroll systems and benefits structure design

Important Note: As this is the founding hire for the team, there will be an initial setup period for payroll and benefits infrastructure. During this transition period, the family will reimburse any medical, dental, and vision insurance costs to ensure seamless coverage from day one.