Requirements
Do you thrive when you are handed complexity and asked to build something out of it?
The Deason Group is seeking a Real Estate Chief of Staff to serve as the operational backbone, trusted representative, and strategic right hand of a top-producing luxury real estate business in San Francisco. This is not a task-execution role. It is a results-driven, systems-building position for someone who genuinely loves creating order, driving momentum, and stepping in wherever the business needs them — from building a CRM on a Tuesday to representing a client at an inspection on a Thursday.
If your natural instinct when entering a business is to ask, "How do we make this better, faster, and more efficient without losing the detail and impact that this level of work requires," you are going to want to keep reading.
About Jonathan Deason and The Deason Group
Jonathan Deason is not your typical real estate agent. With more than 400 homes sold, over $600 million in closed sales, and 50-plus five-star client reviews, he has spent nearly two decades building one of the most respected practices at Vanguard Properties, San Francisco's most trusted luxury brokerage.
Jonathan specializes in representing buyers, sellers, and residential developers throughout Noe Valley, Castro District, Dolores Heights, Corona Heights, Pacific Heights, and Eureka Valley. He is particularly known for guiding developers, homeowners, and investors through property design, renovation, and development strategies that maximize market appeal and long-term return on investment — a perspective made sharper by the fact that he designed and built his own San Francisco home in collaboration with architect Owen Kennerly. He brings firsthand construction and design experience to every project he advises on.
His background as both a tax attorney and a real estate attorney gives his clients — and his team — a distinct advantage. Contracts, negotiations, disclosures, and transaction risk are not abstractions here. They are analyzed with legal precision, and that standard extends to everything the Deason Group touches.
Beyond real estate, Jonathan serves on the Board of Directors of Horizons Foundation and the Randall Museum, where he is a member of the Executive Committee. He holds a Commercial Pilot Certificate with multi-engine and instrument ratings, flies a Cirrus SR22T, and is a certified sailboat skipper on San Francisco Bay. He earned a BA in Art History from UC Berkeley and a JD from UC Law San Francisco, where he served on the Law Review.
The Deason Group currently includes Jonathan and two licensed agents who are experienced, self-directed, and led by Jonathan. The team has already closed $70,000,000 in production this year alone. The infrastructure now needs to catch up to the momentum, and Jonathan is ready to build it the right way, with the right operator by his side. The trajectory is clear. The next chapter is being built right now.
About the Role
Jonathan is not someone who needs to be managed. He handles his own calendar and email, moves with urgency and intention, and leads his agents directly. The team also has an existing transaction coordinator who oversees the contract and offer process during regular business hours. For urgent after-hours needs, you are the person who steps in.
What Jonathan needs now is a Chief of Staff who matches his energy, thinks several steps ahead, and takes full ownership of the systems, people, and infrastructure that enable this business to run and scale.
Jonathan is out of the city approximately 40 percent of the time. When he is traveling, you are the Deason Group. That is not a figure of speech. It shapes how this role is built, and it is one of the most important things to understand about it.
This is a locally remote position requiring residence within approximately one hour of Jonathan's Vanguard Properties office in San Francisco, where regular in-office time is expected. Core business hours are 8:30 AM to 6:00 PM, and this role is entirely results-based. Real estate does not always follow a schedule, and there will be moments — not daily, but when they count — when an offer needs to go out at 9 PM or a transaction issue needs to be handled before Monday morning. You are the person who handles it.
What You Will Be Doing
Operations and Systems — the core of this role
Own, build, and maintain the CRM. This is one of your favorite activities, not a chore.
Build SOPs from scratch and keep them up to date as the business evolves.
Manage vendors, consultants, and external partners across the business.
Identify gaps and inefficiencies before they become problems.
Research and implement better tools and solutions when the existing ones are not working.
Hire, train, and manage a virtual assistant, and determine what to delegate so everyone on the team operates at the right level.
Facilitate regular team check-ins and meetings that keep communication strong and the business moving forward.
Transaction and Deal Momentum — keeping deals and people moving
The transaction coordinator handles contracts and offer preparation during regular business hours. Your role on the deal side of the business is to keep the right people informed, ensure nothing stalls, and ensure Jonathan can stay fully in his lane as the lead agent and advisor. You are the connective tissue between the deal, the team, and the client experience. Deals close cleanly here because someone is always watching the full picture, and that someone is you.
Representing the Deason Group — approximately 10 to 15 percent of your time
This is one of the most important dimensions of the role, and it is worth understanding fully. Because Jonathan is out of the city roughly 40 percent of the time, this business needs a trusted extension who can step in and represent it with complete confidence. That means conducting showings, hosting open houses, meeting clients, attending inspections and vendor meetings, and showing up to any situation where the Deason Group needs a face, a voice, and someone who can be trusted to handle it the right way.
This is not a support function. It is a trust function. The right person will take it seriously and do it well.
While we would prefer someone with an active CA real estate license, we do not require one to apply. You do need the presence, professionalism, and judgment to represent a top-producing business with confidence.
Personal and Property Coordination — approximately 10 percent of your time periodically
Light coordination across Jonathan's properties and projects that require on-the-ground logistics. As a Chief of Staff, your instinct is to identify what needs to happen and route it appropriately — whether that means handling it yourself, tasking the VA, or engaging the right vendor or service. You are not the one on the ground for everything. You are the one who makes sure the right person is, and that it gets done right.
We Know You
You keep your leader informed at a high level so he is never caught off guard. When details are needed, you have them because you are that organized. When you hit a snag, you draw on your experience, think critically, and come to the table with solutions rather than just problems.
You think in systems and ownership. When something lands on your plate, your first instinct is to assess whether it should stay there or be routed to someone who can handle it better. You know the difference between what requires your judgment and what can be delegated to a VA, a vendor, or a task service — and you make those calls without being asked.
You understand the value of a healthy team environment. Regular check-ins and structured communication are not overhead to you. They are how great teams stay aligned and great businesses keep moving. You show up to those conversations prepared, present, and solutions-oriented.
No job is too big or too small. You roll up your sleeves without hesitation and take pride in the outcome, regardless of what it took to get there. You approach your own life with the same intentionality you bring to work: personal and professional development, a healthy mindset, and a genuinely positive attitude are values you actually live.
You bring a servant's heart to high-performance work. You are motivated by building something meaningful, supporting someone doing important work, and being part of a business that is growing with intention.
San Francisco Is Not Just a Location Requirement
This is a locally remote position. You must live within San Francisco or within approximately one hour of the Vanguard Properties office, and you must genuinely know this city.
Not just the neighborhoods and the market, but the pace, the culture, the nuances, and the way this city operates. Whether you were born and raised here, built your career here, or are returning because this is where you belong, San Francisco is your city. You know the luxury landscape, you understand the market, and you are invested in staying and growing here long-term. This is not a role for someone relocating to explore. It is a role for someone who is already rooted or coming home.
You Are the Right Fit If
You have direct experience in real estate operations, and you know the San Francisco market well.
You are a natural systems thinker who finds genuine satisfaction in building a CRM, writing an SOP, and creating structure where there was none.
You know what to delegate, to whom to delegate it, and how to follow up without micromanaging.
You know how to keep deals and people moving without stepping into lanes that belong to someone else. You respect clear ownership and thrive within it.
You communicate directly and honestly. You will say "I don't know" or "I think there is a better approach" before saying yes and underdelivering.
You take ownership of outcomes, not just tasks. You follow up, close loops, and do not let things fall through the cracks.
You operate with urgency as your default, not in response to a crisis.
You understand that judgment, discernment, and outcomes are what matter here. You are trusted to make good calls, and you take that responsibility seriously.
You are ready for a role where your contribution is real, visible, and built to last.
The Bigger Picture
This role has a long runway. As the business grows, so does your opportunity. Adding support staff, shaping team structure, and stepping into an increasingly strategic seat alongside Jonathan are all on the table for the right person. He is not filling a vacancy. He is building something, and he wants someone who wants to build alongside him.
The Details
Base Salary: $150,000 – $170,000, commensurate with experience, in addition to a performance-based bonus
Time Off: Unlimited vacation and paid holidays
Benefits: Company contribution toward medical benefits of your choosing
Work Structure: Locally remote with regular in-office time at Vanguard Properties, San Francisco. Must reside within approximately one hour of the office.
Hours: 8:30 AM – 6:00 PM, results-based
How to Apply
This is a full-time, direct-hire placement with our client. Candidates who reach out to the client directly may be disqualified from consideration. If you would like more information about Pro R.E.A. Staffing and our other open positions, please visit www.proreastaffing.com.
We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.