Event Staffing Jobs in Silver Spring, MD (NOW HIRING)

Event Sales Manager

Job Summary

Fleetwood Farm Winery is seeking an experienced, highly organized Event Sales & Venue Manager to lead the sales, planning, team management, and operational execution of weddings, corporate events, private events, and winery events. This department leadership position is responsible for the full event lifecycle—from lead generation, inquiries, and venue tours through booking, planning, staffing, execution, and post-event follow-up.

The Event Sales Manager directly manages the Sales & Events Team and coordinates the staff, vendors, facilities, and resources required to successfully execute each event.

This position also oversees the readiness and presentation of Fleetwood's wedding and event spaces, including cleaning, maintenance coordination, utilities, vendor services, and venue improvements.

The ideal candidate combines strong wedding and event sales experience, leadership ability, operational expertise, and exceptional hospitality, with a hands-on approach and strong sense of ownership.

Sales & Business Development

• Manage the full sales cycle from initial inquiry through booking, event execution, and post-event follow-up.
• Respond to leads promptly and conduct venue tours, walkthroughs, and client planning meetings.
• Develop new wedding, corporate, and private-event business through prospecting, networking, and relationship building.
• Create proposals, negotiate contracts, collect deposits, and maintain accurate client and event records.
• Manage the sales pipeline, bookings, follow-up, and conversion activity through the company's CRM.
• Build and maintain strong relationships with clients, wedding planners, corporations, hotels, vendors, and referral partners.
• Identify opportunities to increase revenue through venue upgrades, Food & Beverage, and additional Fleetwood offerings.
• Collaborate with Marketing on initiatives to increase bookings, brand awareness, reviews, and customer loyalty.
• Participate in appropriate networking, wedding-industry, and community events.

Event Planning & Execution

• Oversee the planning and execution of weddings, corporate events, private events, and winery events.
• Coordinate event timelines, layouts, staffing, vendors, rentals, Food & Beverage, setup, breakdown, and other event logistics.
• Conduct final walkthroughs and ensure event details are accurately communicated to internal teams and vendors.
• Ensure event spaces, staffing, vendors, equipment, supplies, and operational resources are prepared prior to each event.
• Provide hands-on leadership during event execution as needed.
• Anticipate and proactively resolve client, staffing, vendor, and operational issues.
• Ensure post-event breakdown, cleaning, venue reset, damage reporting, and follow-up are completed.
• Maintain event SOPs, checklists, tracking systems, and operational standards.

Sales & Events Team Leadership

• Lead, manage, coach, and develop the Sales & Events Team, establishing clear expectations, priorities, and accountability.
• Provide day-to-day direction to ensure sales, planning, administrative, venue, and event responsibilities are completed accurately and on time.
• Conduct regular team meetings and individual check-ins to review sales activity, upcoming events, client needs, staffing, and operational priorities.
• Hold team members accountable for client communication, CRM management, follow-up, event documentation, venue standards, and successful event execution.
• Partner with the General Manager on hiring, onboarding, training, performance management, and staffing levels.
• Develop and maintain appropriate training materials, SOPs, and cross-training procedures.
• Foster a collaborative, professional, accountable, and hospitality-focused team culture.

Event Staffing & Scheduling

• Develop and manage event staffing plans and schedules based on the event calendar, guest counts, service requirements, setup and breakdown needs, and approved labor budgets.
• Ensure appropriate staffing for event leads, event staff, setup/breakdown, cleaning, and other operational support.
• Communicate schedules, assignments, call times, and responsibilities to team members.
• Monitor labor usage to ensure staffing is operationally effective and financially responsible.
• Assign responsibilities for each event and ensure clear ownership and deadlines.
• Proactively identify staffing or operational gaps and resolve them before they impact the guest experience.

Venue, Vendor & Operational Management

• Maintain overall accountability for venue readiness, cleanliness, presentation, safety, and functionality of wedding and event spaces.
• Coordinate cleaning schedules, venue inspections, preventative maintenance, repairs, utilities, and property service needs.
• Monitor venue furniture, equipment, décor, storage areas, event supplies, and infrastructure.
• Coordinate approved maintenance and improvement projects with the General Manager and appropriate contractors.
• Identify opportunities for venue upgrades, beautification, operational improvements, and guest-experience enhancements.
• Manage event-related vendors and service providers, including caterers, rental companies, cleaning services, contractors, and other partners.
• Coordinate vendor schedules, access, deliveries, setup, service requirements, breakdown, pickups, and returns.
• Ensure vendors comply with Fleetwood's policies, timelines, and service standards.
• Maintain current vendor information, pricing, service agreements, and relevant documentation.
• Ensure the venue is restored to Fleetwood standards following every event.

Food & Beverage Oversight

• Collaborate with Fleetwood's Food & Beverage Team and approved caterers to ensure consistent, high-quality service.
• Coordinate Food & Beverage timelines and operational requirements with the overall event plan.
• Maximize opportunities to upsell Fleetwood Food & Beverage offerings and increase in-house event revenue.
• Ensure outside caterers comply with Fleetwood's venue requirements and operational standards.
• Proactively resolve Food & Beverage service, staffing, timing, or logistical concerns.

Financial & Administrative Management

• Maintain accurate contracts, event records, payment schedules, client files, and CRM information.
• Ensure deposits, invoices, payments, and financial documentation are processed accurately and on time.
• Monitor event revenue, labor, operating expenses, purchasing, and vendor costs.
• Work with the General Manager and Accounting/Finance Manager to maintain accurate event financial information.
• Identify opportunities to increase revenue, control expenses, improve margins, and maximize profitability.
• Assist with annual sales goals, event budgets, and forecasts.
• Provide regular reporting on sales pipeline, bookings, revenue, staffing, operational needs, and department performance.

Qualifications

• 3–5 years of experience in event sales, planning, venue management, or hospitality required.
• Wedding industry experience required.
• Leadership experience managing or developing teams and/or event venues required.
• Proven ability to schedule staff and manage event labor effectively.
• Strong sales skills with a track record of converting leads into bookings and developing repeat and referral business.
• Excellent leadership, communication, organization, and client relationship skills.
• Experience with event operations, vendors, maintenance, and facility coordination.
• Working knowledge of budgeting, contracts, invoicing, CRM systems, and labor management.
• Strong negotiation, revenue-generation, and problem-solving skills.
• Ability to lead cross-functional teams, delegate responsibilities, and hold staff accountable.
• Ability to manage multiple events and priorities in a fast-paced environment.
• Flexible schedule, including evenings, weekends, and holidays.
• Hands-on leadership style with accountability for sales, team performance, event execution, profitability, and venue readiness.

Salary Range: 

• Base salary of $55,000–$65,000, depending on experience, plus commission. With successful sales performance, the anticipated total annual earning potential is $90,000–$100,000.