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

Chesapeake Manor Vineyard

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Wine Tasting Room Shift Manager