Guest Experience & Fulfillment Specialist

About Crave Locally

Crave Locally is an agritourism discovery and booking platform helping guests discover and book distinctive experiences across Northern Virginia and the broader DMV region.

We work directly with wineries, breweries, farms, restaurants, transportation providers, and other local businesses to create curated experiences for couples, families, celebrations, private groups, and organizations.

As we grow, we are looking for someone who can become the human face behind the Crave Locally guest experience.

The role

We are looking for a highly responsive, organized, and personable Guest Experience & Fulfillment Specialist to help turn customer requests into memorable experiences.

A major part of the role will be managing requests that come through our Personalized Experience Matchmaker™. Guests tell us what they are looking for — who they are traveling with, what they enjoy, whether they need transportation, their budget, preferred dates, and other preferences.

Your job is to carefully understand that request, identify the best-fit Crave Locally experience or itinerary, communicate the recommendation clearly and warmly, and help move the guest from inquiry through booking.

You will also help coordinate reservations with our venue and transportation partners and make sure that every detail is correct before the experience takes place.

This is a flexible role with the opportunity to grow significantly as Crave Locally expands. For the right person, it could evolve into Head of Guest Experience.

Guest experience & Matchmaker fulfillment

• Review incoming Matchmaker requests and other guest inquiries
• Pay close attention to each guest's preferences, timing, group size, budget, interests, transportation needs, dietary considerations, and special requests
• Recommend the most appropriate Crave Locally experience or create a customized option when needed
• Respond to guests quickly, professionally, and warmly
• Answer questions and help guests decide among options
• Follow up appropriately when a guest has not yet booked
• Provide a personalized concierge-style experience throughout the process

Booking & experience coordination

• Confirm availability with wineries, breweries, farms, restaurants, transportation providers, and other partners
• Coordinate reservations across multiple venues when needed
• Confirm pricing, timing, guest counts, and special requirements
• Make sure all components of an itinerary work together
• Maintain clear and accurate booking records
• Communicate final details to guests and partners
• Help resolve changes or issues quickly when they arise

Guest communication

• Serve as a primary point of contact for guests before their experience
• Communicate clearly by email, phone, text, and other channels as appropriate
• Make customers feel that someone is personally looking after their experience
• Anticipate questions and potential problems before they occur
• Maintain Crave Locally's warm, professional, and highly responsive communication style

Business development support

As capacity allows, the role may also include:

• Reaching out to community groups, clubs, associations, companies, and other potential group customers
• Following up with prospective group organizers
• Helping identify opportunities for private and group experiences
• Supporting repeat bookings and referrals

What we're looking for

The primary responsibility is always delivering an excellent guest experience and converting qualified inquiries into successfully fulfilled bookings. The right person is:

• An excellent communicator — warm, polished, clear, and comfortable interacting with customers
• Extremely detail-oriented
• Highly responsive and able to follow up quickly
• Naturally organized and comfortable coordinating multiple moving pieces
• Good at listening and identifying what someone actually wants
• Able to make thoughtful recommendations rather than simply sending generic options
• Comfortable communicating with business owners and hospitality partners
• Resourceful when plans change or an option is unavailable
• Reliable and able to follow a customer request through from inquiry to completion

Relevant background

Experience in hospitality, travel, concierge services, events, customer success, tourism, sales, or guest services would be particularly relevant, but exceptional communication skills, judgment, and attention to detail matter more than a specific background.

Knowledge of Northern Virginia, Loudoun County, Virginia wine country, or the DMV hospitality scene is a plus.

Schedule & working style

This is a flexible role, but responsiveness is important. Customer requests may arrive throughout the day, and we want guests to receive a timely response rather than waiting several days for assistance.

The role does not require traditional fixed office hours, but the successful candidate should be able to monitor incoming requests and respond within agreed service standards.

Some weekend communication may occasionally be needed because many Crave Locally experiences take place on weekends.

Compensation

The specific structure will be discussed based on experience and expected availability.

• A base level of compensation for ongoing guest-experience and coordination responsibilities
• Additional commission or performance-based compensation tied to successfully fulfilled bookings and/or group business

Growth opportunity

This role is intended to grow with Crave Locally. A successful team member who demonstrates excellent guest service, strong judgment, operational reliability, and leadership potential could ultimately take responsibility for the broader customer journey and grow into the role of Head of Guest Experience.

That role could eventually oversee guest communications, Matchmaker fulfillment, booking operations, concierge services, customer feedback, repeat business, and additional guest-experience team members.