Chief Of Staff

Pro R E A Staffing•San Francisco, CA

5d•Hybrid

About The Position

This role is for an individual who can proactively identify and solve business problems, build and run the operational engine of a high-producing real estate business, and represent the principal with confidence. The Chief of Staff will manage the operational infrastructure, including CRM, SOPs, vendor management, and virtual assistant oversight, ensuring deals and people are moving efficiently. This position requires a proactive, organized, and urgent approach to problem-solving and task completion, with the ability to discern when to handle issues personally and when to delegate. The principal, Jonathan Deason, is a successful luxury real estate practitioner in San Francisco with extensive experience and a strong network. He requires a Chief of Staff who can operate autonomously, make sound judgment calls, and maintain the momentum of the business, especially during his frequent travel (approximately 40% of the time). The Chief of Staff will act as Jonathan's trusted extension, handling tasks such as showings, inspections, and client meetings on his behalf, as well as coordinating logistics across properties and projects.

Requirements

Deep understanding of the San Francisco market, pace, and culture, particularly in the luxury landscape.
Proven ability to act as a systems thinker, with a genuine interest in building CRMs and writing SOPs.
Direct communication style.
Ownership of outcomes rather than tasks.
Ability to bring solutions rather than problems.
Skill in delegation, knowing what to delegate, to whom, and how to follow up without micromanaging.
A servant's heart combined with a high-performance standard.
Positive attitude and investment in personal growth.
Willingness to perform any task required, regardless of perceived level.
Must reside within approximately one hour of the office.
Must be able to work results-based hours, typically 8:30 AM – 6:00 PM, with flexibility for urgent after-hours or weekend needs.

Nice To Haves

Experience in real estate transactions or operations.
Experience working with high-producing individuals or businesses.
Background in law or tax, given the principal's qualifications.

Responsibilities

Build and run the operational infrastructure of the business, including CRM ownership, SOPs, vendor management, and virtual assistant oversight.
Ensure deals and people are moving efficiently to keep the principal focused on core activities.
Handle urgent issues that arise after regular business hours.
Serve as the principal's trusted extension in the field, conducting showings, attending inspections, and meeting clients on his behalf.
Coordinate logistics across properties and projects, determining what to handle directly and what to delegate.
Manage transactions and provide support during off-hours, including evenings and weekends, as needed for urgent matters.