Executive Assistant to Managing Broker Chess Real Estate Services - Greenwich, CT 06831 Full-Time | In-Office | $25/hour About the Role Chess Real Estate Services (CHESS) is seeking a highly organized, proactive Executive Assistant to the Managing Broker . This is not a traditional administrative position. We're looking for a long-term partner and key player in the growth of CHESS who can stay two steps ahead, take ownership, solve problems, embrace technology, and help keep the Managing Broker focused on his highest-value activities: prospecting, appointments, client relationships, negotiations, leadership, and closing business. The position combines executive support, real estate operations, CRM and database management, client care, office coordination, project management, marketing, social media, and technology.

What You'll Do:

Executive & Administrative Support Manage the Managing Broker's calendar, appointments, meetings, inbox, calls, travel, and daily priorities. Help maintain accountability for prospecting, follow-up, call lists, and daily activity tracking. Prepare client, listing, buyer, meeting, and presentation materials. Coordinate showings, meetings, appointments, and business events. Track important invoices, subscriptions, professional dues, licenses, continuing education, and compliance items. Maintain and improve company processes, checklists, handbooks, and standard operating procedures. Handle sensitive client, company, financial, and personal information with discretion. CRM, Database & Client Experience Maintain accurate records, call notes, tasks, tags, and follow-up plans in BoldTrail CRM . Make sure leads, clients, past clients, VIPs, and referral partners receive consistent follow-up. Help execute email, direct-mail, video, gifting, birthday, closing, referral, and client-appreciation programs. Assist with client communication, showing feedback, reviews, surveys, testimonials, and post-closing care. Help CHESS provide a professional, responsive, high-touch client experience . Real Estate & Transaction Support Assist with listing launches, buyer and seller files, property marketing, showings, offers, and transaction checklists. Track important transaction milestones, documents, deadlines, and follow-up. Help coordinate communication among clients, lenders, attorneys, cooperating brokers, inspectors, and vendors. Maintain organized transaction files for business conducted in New York, New Jersey, and Connecticut . Help ensure established CHESS transaction and compliance systems are consistently followed. Marketing, Technology & Social Media Work with Google Workspace, BoldTrail, Asana, ManyChat, Metricool, Canva , and other company platforms. Manage recurring projects, tasks, deadlines, and marketing calendars. Assist with social-media posting and scheduling across Instagram, Facebook, and TikTok . Perform basic-to-intermediate video editing , including short-form vertical content, captions, graphics, and repurposing existing content. Help distribute video and marketing content to the CHESS database. Assist with mailers, Just Listed/Just Sold campaigns, presentations, events, and other marketing initiatives. Troubleshoot routine technology issues and proactively research solutions. You don't need to know every CHESS platform on Day One. You do need to be comfortable learning technology quickly and figuring things out. Office, Events & Team Support Maintain a consistent in-office presence and help open, prepare, organize, and close the office as required. Professionally greet clients, referral partners, vendors, and other visitors. Assist with the main business line, office supplies, meeting preparation, and general office operations. Coordinate and attend client events, networking events, educational programs, and company activities. Assist with onboarding future employees, interns, virtual assistants, agents, and vendors as CHESS grows. Who We're Looking For Self-motivated with a high sense of urgency . Extremely organized and detail-oriented. Proactive—you naturally ask, "What needs to happen next?" Resourceful and able to exercise good independent judgment. Strong written and verbal communicator. Professional and confident when interacting with clients and business professionals. Comfortable managing multiple priorities and changing deadlines. Comfortable holding yourself and the Managing Broker accountable. Tech-savvy and willing to learn new systems quickly. Comfortable with social media and basic video editing. Positive, coachable, growth-minded, and team-oriented. Discreet with confidential information. Interested in a long-term position with growth potential . Prior administrative, executive-assistant, operations, real estate, or client-service experience is preferred. CRM, social-media, and video-editing experience are also preferred. Real estate experience is helpful but not required for the right candidate. Your Three Primary Objectives 1. Keep the Managing Broker in His Highest-Value Role Protect the Managing Broker's time so he can concentrate on prospecting, appointments, relationships, negotiations, leadership, and closing business. 2. Execute the CHESS Database & Client-Care Plan Help ensure leads are followed up with, clients are cared for, relationships are maintained, and CRM systems are consistently executed. 3. Execute the CHESS Operating System Help own the administrative, transaction, technology, marketing, project-management, and office execution that keeps the company moving. Pay & Benefits Income Starting compensation: $25/hour during a 90-day introductory period, equivalent to approximately $52,000 annually at 40 hours per week. Following successful completion of the introductory period, compensation and employment status will be reviewed based on performance, role fit, and responsibilities. Hours Monday-Friday, 8:00 AM-5:00 PM . This is primarily an in-office position in Greenwich, Connecticut . Occasional evenings or weekends may be required for client, networking, or company events. Paid Holidays / Days Off CHESS provides 10 paid company holidays annually , including New Year's Day, Martin Luther King Jr. Day, Memorial Day, Juneteenth, Independence Day, Labor Day, Thanksgiving Day, the day after Thanksgiving, Christmas Eve, and Christmas Day. Vacation & Sick Time Full-time employees receive 10 paid vacation days annually following successful completion of the 90-day introductory period , subject to advance scheduling and approval. Paid sick leave is provided pursuant to CHESS policy and applicable Connecticut law. Additional Benefits Approved business mileage is reimbursed pursuant to company policy.

Health Benefit:

Following successful completion of the 90-day introductory period, eligible full-time employees may receive up to $400 per month toward qualified health insurance and medical expenses through the company's Health Reimbursement Arrangement , subject to plan terms and eligibility requirements. About Chess Real Estate Services

C.H.E.S.S.

— Closing Homes, Executing Solid Strategies Chess Real Estate Services is a growing real estate brokerage based in Greenwich, Connecticut , serving clients throughout New York, New Jersey, and Connecticut . Our business is built around relationships, professional representation, strong systems, technology, accountability, continuous improvement, and exceptional client service. We're looking for someone who doesn't simply want to work for CHESS , but wants the opportunity to grow with CHESS and become an important part of the company's future.

Pay:

$25.00 per hour Expected hours: 40.0 per week

Benefits:

Paid time off

Work Location:

In person