Now Hiring: Wedding & Event Sales Manager

Location

On-site at Willowood in Boonsboro, MD, for tours + key events; remote admin/outreach time

Role Summary

The Wedding & Event Sales Manager owns the sales pipeline for weddings and private events at Willowood — from first inquiry through signed contract, and from partner outreach through a high-converting tour experience. This role is equal parts relationship-builder, premium sales professional, and operational handoff quarterback. Success means: consistent, qualified leads, strong tour-to-booking conversion, clear contracting, and seamless transition to operations once booked.

Key Responsibilities

1) Lead Management & Conversion (Core)

• Respond to inbound inquiries quickly and professionally (email/text/calls), using Willowood’s brand voice and templates.
• Qualify leads (date, guest count, budget, vibe, vendor flexibility, needs) and guide prospects to best-fit packages.
• Schedule and run site tours that convert — confident storytelling, thoughtful discovery questions, clear next steps.
• Build and manage a sales pipeline/CRM: stages, follow-ups, notes, forecasts, and close plans.
• Close contracts: present proposals, address objections, negotiate within pre-set parameters, and secure deposit/signature.

2) Proposal, Contracting & Client Journey

• Prepare quotes/proposals and ensure accuracy on pricing, inclusions, add-ons, and event requirements.
• Coordinate contract execution, deposit collection schedules, and key deadlines.
• Maintain meticulous documentation so every booked event has a clean internal handoff (timeline, inclusions, constraints, special requests).
• Set expectations early and clearly to protect guest experience and Willowood standards (noise, capacity, vendor rules, property care).

3) Planner & Partner Network

• Build and maintain relationships with high-end wedding planners, corporate retreat planners, and select vendors.
• Develop preferred partner relationships (planners, caterers, rentals, florals, photography, transportation) that elevate the brand.
• Represent Willowood at industry events, tours, open houses, and selective networking opportunities.
• Coordinate familiarization tours and hosted planner days to generate top-tier referrals.

4) Brand, Marketing Support & Content Inputs 

• Provide feedback loops to marketing: what prospects ask, what objections arise, what sells, and what doesn’t.
• Help keep listing content accurate: capacity notes, seasonal highlights, photo wishlist, package clarity.
• Support review generation and post-event testimonial.
• Help create and post some social media content in collaboration with the marketing team.

5) Team Collaboration & Operational Handoff

• Collaborate with operations to ensure feasibility and exceptional execution.
• Transition clients cleanly after booking (or remain involved through planning checkpoints, depending on your workflow).
• Participate in weekly pipeline meetings with leadership: booked/forecasted revenue, lead sources, conversion rates, and next actions.

Success Metrics (How You’ll Be Measured)

• Response time to new inquiries (speed-to-lead)
• Qualified lead rate (right-fit inquiries)
• Tour-to-booking conversion rate
• Booking volume and revenue against monthly/quarterly targets
• Pipeline accuracy (forecast vs actual)
• Partner-driven leads (planner/vendor referrals)
• Client experience quality (communication, clarity, professionalism)

Required Qualifications

• 3+ years in wedding/event sales, luxury hospitality, venues, hotels, or high-touch client services.
• Proven ability to close premium experiences (not just “take orders”).
• Strong writing skills (clear, confident, warm emails and proposals).
• Organized and systems-driven: CRM discipline, follow-up excellence, accurate documentation.
• Comfortable hosting tours and building rapport with a wide range of clients.
• Weekend availability as needed for tours/events (not every weekend, but aligned to the business).

Preferred Qualifications

• Experience selling full-buyout venues, retreats, estates, or boutique hotels.
• Existing planner network in DC/MD/VA/PA.
• Familiarity with venue contracts, vendor requirements, and event logistics.
• Experience with CRMs.

Traits That Fit Willowood

• Taste and discernment — you understand luxury without being “stuffy.”
• Calm confidence — you can lead a couple or a client through big decisions.
• Storyteller — you can sell a feeling, not just a space.
• Highly responsive — follow-up is your superpower.
• Detail-aware — you protect the property and the brand through clear expectations.

Compensation 

This is a 100% commission sales role based on gross collected (net of pass-through) revenue. 

Schedule & Work Expectations

• Flexible schedule with responsiveness standards
• On-site for tours and select event days
• Peak sales activity evenings/weekends (when couples are available)

How to Apply

Submit your resume to [email protected] with a short note explaining:

1. A wedding/event you’re proud of selling (and what made it convert)
2. How would you approach this opportunity at Willowood
3. Fun fact/something special we should know from the get-go 

About Willowood Washington

Willowood Washington is a private, 66-acre historic estate in Maryland designed for full-buyout weddings, retreats, and milestone gatherings. With a restored farmhouse, heritage suites, expansive grounds, and a storied 1850s barn, Willowood blends hospitality and heritage to create unforgettable celebrations.