Sentinel

Bespoke Private Service • San Francisco, CA

1d • Onsite

About The Position

A distinguished San Francisco-based family office seeks a high-caliber Chief of Staff to serve as the operational leader, partnering with the Chief Operating Officer on strategic direction while managing daily coordination across household, travel, and logistics domains. This pivotal role provides senior-level oversight of personal service operations, managing an established team of specialized Personal Assistants while ensuring seamless coordination across multiple properties. The successful candidate will function as the COO's trusted lieutenant, an orchestrator who enables specialists to excel while never being afraid to roll up their sleeves and do the work themselves. We seek someone scrappy, resourceful, and hands-on, who sees the full operational picture and can direct the team toward strategic objectives with minimal oversight. This position requires a 24/7 mentality; understanding that supporting a highly mobile Principal means building systems and delegation frameworks that ensure continuous coverage while maintaining the highest standards of service. Communication excellence is paramount in this role. The ideal candidate is a strong communicator who excels at both upward communication with the Principal and COO, translating operational complexity into clear, actionable updates, as well as downward communication with the team, ensuring alignment, clarity of priorities, and a culture of accountability and collaboration. We seek a candidate with exceptional horsepower, high EQ and IQ in equal measure, who thrives on building and implementing operational systems. The ideal professional is eager, ambitious, and possesses the rare ability to anticipate needs through deep understanding of the Principal's priorities. This role demands someone who can transform reactive operations into proactive service excellence while maintaining absolute discretion and confidentiality. This opportunity offers the chance to shape operations within a sophisticated family office environment, working alongside a team that values responsiveness, transparency, and best-in-class standards. The role is ideal for a systems thinker who wants to build infrastructure that enables the COO to step back from day-to-day personal service involvement while ensuring nothing falls through the cracks.

Requirements

• Minimum seven years of progressive experience in estate management, private family office operations, chief of staff roles, or luxury hospitality with demonstrated success overseeing high-performing teams and multi-property portfolios.
• Exceptional communication skills with demonstrated ability to communicate effectively across all levels, translating strategic priorities into clear direction for the team while providing concise, relevant updates to the Principal and COO.
• Proven ability to build, implement, and optimize operational systems. A true systems thinker who can design scalable processes for property management, vendor coordination, and team delegation.
• Scrappy, resourceful mindset with willingness to roll up sleeves and execute directly when needed, while also effectively delegating and orchestrating specialists to excel in their domains.
• Strong track record of managing and developing teams, including setting priorities, delegating effectively, and ensuring accountability while fostering a collaborative environment.
• Exceptional anticipatory skills with demonstrated ability to understand principal priorities deeply and act proactively to solve problems before they arise.
• Advanced proficiency in digital project management platforms, particularly Asana, with enthusiasm for testing and implementing new software solutions that improve operational efficiency.
• High emotional intelligence combined with exceptional discretion. Able to handle confidential information with absolute professionalism and maintain trust in all interactions.
• 24/7 operational mindset with the maturity to manage personal boundaries while ensuring continuous coverage; able to coordinate weekend and off-hours support through effective delegation and team scheduling.
• Strong vendor management capabilities with experience negotiating contracts, maintaining service standards, and building productive relationships across property maintenance, household services, and specialty providers.
• Interest and aptitude in real estate operations and property management, with the ability to oversee maintenance, upkeep, and preparation across multiple residences.
• High learning agility with a bias toward action. Someone who figures things out quickly, moves fast on time-sensitive matters, and always closes the loop on tasks and communications.
• Ability to travel regularly to family properties for vendor coordination, property oversight, and maintenance of service standards across all locations.

Responsibilities

• Strategic Partnership & Communication: Partner with the COO on strategic direction while serving as the communication hub for the organization. Ensure clear, consistent messaging between the Principal, COO, and the PA team. Translate high-level priorities into actionable plans and provide regular, concise updates on operational status.
• PA Team Leadership: Provide senior-level oversight to the existing team of specialized Personal Assistants, including task delegation, priority setting, and performance management. Function as the orchestrator who enables specialists to excel while remaining hands-on when situations demand. Serve as the primary point of escalation, enabling the COO to maintain only minimal involvement in personal service operations.
• Personal Service Operations: Oversee all aspects of personal service delivery, ensuring seamless coordination of scheduling, logistics, and household needs. Build systems that provide continuous coverage and proactive support for a highly mobile Principal.
• Multi-Property Management: Coordinate maintenance, upkeep, and preparation across multiple residences with the support of the PA team. Ensure properties are guest-ready and appropriately provisioned ahead of Principal arrivals, including wardrobe coordination and personal item logistics.
• Wardrobe & Personal Logistics: Design and implement systems to manage clothing and personal items across locations, ensuring the Principal has what they need at each property. Oversee preparation of toiletries, wardrobe selection, and personal preferences ahead of arrivals.
• Vendor Management: Maintain relationships with vendors and service providers across all properties. Negotiate contracts, ensure service quality, and coordinate scheduling for property maintenance, household services, and specialty needs.
• Systems Development: Build operational infrastructure using Asana and complementary tools to create transparency, accountability, and efficiency. Continuously evaluate and implement new technologies that improve team coordination and service delivery.
• Scheduling Coordination: Manage complex scheduling across team members, vendors, and properties. Ensure appropriate coverage for weekends and off-hours through strategic delegation and advance planning.
• Confidentiality & Discretion: Uphold the highest standards of privacy and professionalism. Handle sensitive information with absolute discretion, sharing only on a need-to-know basis and building trust through reliable, respectful interactions.
• Strategic Communication: Function as the operational hub between the COO and the PA team, filtering information appropriately and escalating only critical matters. Maintain transparent communication with stakeholders and ensure nothing falls through the cracks.

Benefits

• Comprehensive Healthcare Coverage : 100% employer-paid health, dental, and vision insurance
• Retirement Planning : 401(k) with 6% employer match
• Time Off: Vacation leaves and paid holidays
• Professional Growth : Professional development opportunities

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed