Transaction & Operations Coordinator
The Gayle Winters Team | Residential Real Estate
Location: Lexington and Winchester, MA offices, in person (private office space in Lexington)
Employment Type: Full-Time, W-2
Compensation: $68,000 to $75,000 base salary, plus a bonus for every transaction that closes, paid monthly
Schedule: Business hours, with flexibility for the occasional evening or weekend client event
Keep 60+ Deals a Year Moving From Contract to Close
The Gayle Winters Team is a Zillow Preferred Team affiliated with Compass, with nearly ten years of momentum behind it. We represent buyers and sellers, we are on pace for about 60 transactions this year, and we expect to reach 100 or more. More agents are joining this fall, with a goal of ten agents by year end.
Gayle is out with clients and builders most days, so she needs a right hand at the office. That is this role. You will keep every deal on track and keep the back office running so our agents can spend their time selling.
This is a proven seat with a clear path. As the team grows, we plan to add a dedicated transaction coordinator, and you can grow into a broader operations leadership role.
What You’ll Do
Run our transactions from contract to close
Open each file, track every critical date (inspection, financing, appraisal, closing), and keep all parties moving: agents, clients, lenders, title, attorneys, and inspectors
Collect and organize every document, spot problems early, and keep agents updated on what is due and what is missing
Coordinate closing logistics and the client follow-up, including the request for a five-star review
Be the go-to person for our agents
Build listing presentation binders, prep for open houses, and handle listing paperwork, photography, signs, and vendor scheduling
Coordinate team meetings, call nights, and client events
Keep our systems and numbers in order
Check Follow Up Boss regularly so leads and activity are logged, and report on pipeline, listings, and year-to-date goals
Update tasks in monday.com so Gayle can see where everything stands at any hour
Help us build and document our processes and checklists as new agents come on board, and use AI tools to work faster
Requirements
What We’re Looking For
Real estate experience: residential transaction coordination, agent or team support, or a closing, title, or real estate paralegal background. You understand the transaction from contract to close and you know the industry moves fast
Strong organization and the ability to keep many files moving at once without dropping details
Comfort with CRMs and transaction or task management tools (we use Follow Up Boss, Compass tools, and monday.com), plus Google Workspace or Microsoft Office
Hands-on experience using AI tools such as Claude or ChatGPT in your work
A strong, professional communicator who can tell an agent or Gayle, respectfully and directly, “this is waiting on you”
Dependable and self-directed. You take ownership, finish what you start, and keep Gayle updated at least every other day without being chased
Able to work in person at our Lexington or Winchester office.
Nice to have: an active real estate license (not required)
This Role Is For You If
You love keeping details and deadlines under control, and you take pride in a closing that goes smoothly
You want to be the right hand to a busy team leader and the go-to person for the agents
You enjoy working in person with a collaborative, fast-moving team
You are comfortable with direct, honest communication, and you speak up when something is stuck
You want a path to grow into a larger operations role as the team doubles in size
Good to Know Before You Apply
This is an in-person role, not a remote one
This is a transaction and operations seat. Marketing, social media, and content are handled by our marketing team, and agent coaching and training are handled by our coach
The schedule is business hours, with an occasional evening or weekend client event
We need someone who can…