Chief Of Staff

Job Description

Job Description

You are the person who walks into a business and immediately sees what is broken, what is missing, and exactly how to fix it. You do not wait to be asked. You are already building the solution.

You have been doing this for years, probably for someone who does not fully realize what they have in you. You are organized in a way that feels effortless to everyone around you, but you know exactly how much intention it takes. You move with urgency. You close loops. You know when to handle something yourself and when to route it to the right person. You take pride in outcomes most people never even notice.

You are ready for a role that truly reflects what you bring.

This Is That Role

Jonathan Deason is a UC Berkeley and UC Law San Francisco graduate, licensed tax and real estate attorney, active commercial pilot, and nearly two-decade Top Producer at Vanguard Properties in San Francisco. With more than 400 homes sold, over $600 million in closed sales, he has built one of the city's most respected luxury real estate practices. He is known for his work with buyers, sellers, and residential developers throughout San Francisco's most competitive neighborhoods, and he brings firsthand design and construction experience to every project he advises on — including his own home in Corona Heights, which he designed and built in collaboration with architect Owen Kennerly. He serves on the Board of Directors of Horizons Foundation and the Randall Museum.

He does not need to be managed. He needs a Chief of Staff. Someone who can build and run the operational engine of this business, represent him with confidence when he is out of the city — which is roughly 40 percent of the time — and make the kind of judgment calls that keep a high-producing business moving without missing a beat.

That is the opportunity in front of you.

What You Will Own

You will build and run the operational infrastructure of this business: CRM ownership, SOPs, vendor management, virtual assistant oversight, and keeping deals and people moving so Jonathan stays focused on what only he can do. A transaction coordinator handles contracts and offer preparation during regular business hours. For any urgent issues that come up after hours, you are the person.

You will also serve as Jonathan's trusted extension in the field — conducting showings, attending inspections, and meeting clients on his behalf. And you will coordinate light logistics across his properties and projects, knowing what to handle directly and what to route to a VA, a vendor, or a task service.

Real estate does not always follow a schedule. When an offer needs to go out at 9 PM or a deal needs attention over the weekend, you handle it. It is not a daily expectation. It is part of working at this level, and you already know that and know how to manage your time well.

We Know You

San Francisco is your city. You know the market, the pace, the culture, and the luxury landscape. You live here, have built your career here, or are coming back because this is where you belong and intend to stay.

You are a systems thinker who genuinely loves building a CRM and writing an SOP. You communicate directly, take ownership of outcomes rather than tasks, and bring solutions rather than problems. You know what to delegate, to whom to delegate it, and how to follow up without micromanaging. You have a servant's heart and a high-performance standard, and you see them as completely compatible.

You are positive, invested in your own growth, and the kind of person who never thinks a job is beneath them.

The Details

• Salary: $150,000 – $170,000 plus performance bonus
• Time Off: Unlimited vacation and paid holidays
• Benefits: Company contribution toward medical benefits of your choosing, paid time off, sick time, and holidays.
• Location: Locally remote; regular in-office time at Vanguard Properties and at the agent's home office in 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 .

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.