Transaction & Operations Coordinator

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

About the Opportunity

The Gayle Winters Team is a growing residential real estate team with nearly ten years of momentum behind it. We represent buyers and sellers, we are a Zillow Preferred Team affiliated with Compass, and we are growing fast: more agents are joining this fall, with a goal of ten agents by year end. We are on pace for about 60 transactions this year and expect to reach 100 or more.

Gayle is out with clients and builders most days, so she needs a right hand at the office. That is this role. You will be the person who keeps every deal on track from contract to close and keeps the back office running so the agents can spend their time selling.

This is not a new seat we are experimenting with. It is a proven role 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

This Role Is Not For You If

• You want to work remotely. This is an in-person role
• You are looking for a marketing, social media, or content role. Our marketing team handles that.
• You want to coach or supervise agents. Our coach handles training and performance
• You prefer a strictly fixed 9-to-5 with no occasional evening or weekend events
• You are new to real estate and looking to learn the industry from scratch. We need someone who can step in quickly

How We Work

We are collaborative and fast-moving. Gayle is direct and honest, and she expects the same from you. If you want a team that is building something, with open communication and a leader who will be glad you speak up, you will do well here.

Benefits

Compensation & Benefits

• $68,000 to $75,000 base salary
• Bonus for every closed transaction, paid monthly
• OTE: between $74,000 to $85,000 per year for top performer
• Two weeks of paid time off plus major holidays
• A private office space and a team that wants you to grow with it