Wine Tasting Room Shift Manager

POSITION TYPE

Part-Time | Hourly Position

POSITION OVERVIEW

Chesapeake Manor Vineyard is seeking a Wine Tasting Room Shift Manager to oversee daily tasting room operations and support an exceptional guest experience. This role serves as the on-shift leader responsible for staff supervision, guest engagement, wine service, and operational flow. The Shift Manager plays a central role in maintaining a welcoming, polished, and hospitality-driven environment while ensuring smooth coordination of wine tastings, food service, and retail sales.

KEY RESPONSIBILITIES

Staff Leadership & Support Provide direction and support to staff during shifts Ensure adherence to dress code and grooming standards Communicate operational updates and priorities Address and resolve staff concerns professionally Support onboarding and staff training initiatives Guest Experience & Hospitality Tasting Room Operations Supervise and support tasting room staff in assigned roles Ensure smooth service flow and staff coordination Maintain a polished, organized, and guest-ready environment Confirm daily signage is properly placed and updated Maintain awareness of winery offerings and daily operations Guest Experience Greet guests and create a welcoming, engaging atmosphere Provide knowledgeable wine recommendations and general visitor information Conduct guided wine tastings, presentations, and tours as needed Promote and sell wine, wine flights, wine club memberships, food and retail products Address guest concerns and service recovery professionally Inventory & Stocking Restock wine and retail inventory as needed Monitor product availability and presentation POS & Transactions Ensure POS systems are fully operational Process transactions including sales, returns, discounts, and employee purchases Maintain accuracy and accountability in cash handling Facility & Cleanliness Standards Maintain cleanliness and organization of the Tasting room, Service areas, Picnic areas, and Restrooms Ensure trash receptacles are emptied and relined as needed Support overall appearance and guest comfort Events Assist with onsite events such as parties, showers, classes, festivals and other promotional events Assist with offsite such as festivals, farmers markets, and other promotional events Qualifications Enthusiasm for wine and hospitality Enthusiasm for talking with customers about wine, food and the vineyard Previous experience in hospitality, retail, or supervisory roles preferred Strong leadership, communication, and organizational skills Comfortable operating POS systems Ability to multitask in a guest-facing environment Working Conditions Active, hospitality-driven environment Standing, walking, and light lifting required Fast-paced guest service setting Additional Responsibilities Maintain current knowledge of wines, menu items, and policies Multitask effectively in a fast-paced environment Complete additional duties as assigned

REQUIREMENTS

Must be at least 21 years of age TIPS certification (or equivalent) required/ Must receive within 90 days of employment Ability to lift up to 30 pounds Reliable transportation Ability to work evenings, weekends, and holidays Team-oriented, dependable, and professional

ORGANIZATIONAL ALIGNMENT

This position operates as part of Chesapeake Manor Vineyard's tasting room leadership team. The Tasting Room Shift Manager reports directly to the Food & Beverage Manager and works closely with management to ensure consistent hospitality standards, smooth daily operations, and an exceptional guest experience. Shift Managers serve as the primary on-floor leaders during assigned shifts, supporting staff performance, guest engagement, and operational flow.

COMPENSATION & BENEFITS

Part-time hourly position with competitive pay of $18/hour base pay + tips Compensation commensurate with experience Additional opportunities to pick up shifts or assist with events and special projects may be available based on business needs.

Benefits may include:

Flexible scheduling Employee discounts Professional development opportunities

ABOUT CHESAPEAKE MANOR VINEYARD

Chesapeake Manor Vineyard is an estate vineyard and winery located on Kent Island in Stevensville, Maryland. Overlooking the Chesapeake Bay, our tasting room offers a relaxed yet refined hospitality experience featuring estate-grown wines, guided tastings, and thoughtfully prepared light fare. We are a growing, dynamic operation that values warmth, professionalism, teamwork, and exceptional guest experiences. Our environment blends wine, hospitality, and culinary offerings in a setting that is both fast-paced and guest-focused.

Pay:

$18.00 - $45.00 per hour

Benefits:

Employee discount Flexible schedule Application Question(s): Are you at least 21 years of age? This role requires evenings, weekends, and holidays. Are you comfortable with this schedule? Are you comfortable standing or walking for the duration of your shift? Do you feel comfortable speaking with guests about wine and making recommendations? Describe your favorite wine and tell us why you like it. Will you be able to reliably commute to Chesapeake Manor Vineyard including during summer hours when traffic is high?

Work Location:

In person