Operations/ Customer Service Lead

Location: Nashoba Valley Winery – Bolton, MA
Position Type: Full-Time
Compensation: $22–$25 per hour (Tipped Position)

ABOUT THE OPERATION

Nashoba Valley Winery is a premier hospitality destination where guests gather to enjoy locally crafted wines, beers, ciders, spirits, tastings, and food in a scenic vineyard setting.

• Spring through Fall: A vibrant 10,000+ sq. ft. outdoor venue known as The Knoll, featuring 100+ tables, sweeping vineyard views, and one to two tasting rooms.
• Winter Season: Operations transition to our indoor seating area, The Pavilion, open Saturdays and Sundays alongside the tasting room.
• Midweek (Winter Months): This role shifts focus to the tasting room and retail shop, working with a small team — and at times independently — to maintain service standards and operational efficiency.

This operation is more than a seating area — it’s an experience. We are looking for a high-energy, hospitality-driven leader to oversee daily operations, elevate team performance, and deliver exceptional guest experiences in a fast-paced, seasonal environment.

POSITION SUMMARY

The Operations / Customer Service Lead is responsible for overseeing weekend shift leads across beverage servers, tasting room staff, Terrace Bar team members, and beverage expediters, while also leading day-to-day operations during the week.

This role serves as the primary on-site operational and guest experience leader. The position focuses on ensuring smooth service operations while maintaining a high level of customer service across all guest-facing areas.

This is a hands-on leadership role. The ideal candidate will be trained in all operational areas — including serving, tastings, tours, POS systems, beverage expediting, guest check-in, and bar service — and capable of executing and leading daily service functions.

During weekday shifts, the Operations / Customer Service Lead will be required to work a specific station while maintaining leadership oversight and accountability for service standards across the property.

SCHEDULE REQUIREMENTS
(Wednesday – Sunday Required)

Mid-Fall & Winter Hours
• Wednesday & Sunday: 10:30 AM – 5:30 PM
• Thursday – Saturday: 10:30 AM – 6:30 PM

Spring – Early Fall Hours
• Wednesday & Sunday: 10:30 AM – 5:30 PM
• Thursday – Saturday: 10:30 AM – 7:30 PM
• Friday hours may vary due to Food Truck Fridays
• One to two weekday shifts may begin at noon

✔ Must be able to lift up to 50 lbs and remain active on your feet for 8–10 hour shifts.

KEY RESPONSIBILITIES

Leadership & Team Management

• Oversee daily operations across Beverage Servers, Check-In Attendants, Terrace Bar staff, Tasting Room team, and Beverage Expeditors
• Lead weekend shift leads and ensure alignment across all service areas
• Hire, train, schedule, and develop team members
• Adjust staffing and responsibilities based on seasonal demand, weather, and guest volume
• Maintain productivity and morale during slower periods
• Foster a culture of accountability, positivity, teamwork, and guest-focused hospitality

Customer Service & Guest Experience

• Set the tone for a welcoming, professional, guest-first environment
• Serve as the point person for guest concerns or service issues
• Lead guest check-in flow and overall service efficiency
• Support beverage and food service during peak periods
• Educate and engage guests about our wines, beers, ciders, and spirits
• Ensure smooth beverage expediting and coordinated service across the venue

Operations & Environment

• Monitor service flow across the 10,000 sq. ft. outdoor venue
• Maintain cleanliness, organization, and presentation across all service areas
• Work cross-functionally with other departments to ensure seamless operations
• Step into hands-on service roles when needed to support the team
• During winter midweek, operate tasting room and retail service.

WHY YOU’LL LOVE WORKING AT NASHOBA

• A beautiful vineyard setting with one of the most scenic views in Massachusetts
• A supportive and team-driven work environment
• Hands-on experience in wine, beer, cider, and spirits hospitality
• A dynamic seasonal atmosphere with variety throughout the year
• Leadership growth opportunities within a growing hospitality operation

If you're ready to lead a hardworking team and help create an exceptional guest experience in one of Massachusetts’ most unique hospitality environments, we’d love to hear from you.

Apply today and become part of the Nashoba experience.

• Minimum 2 years of hospitality or customer service experience
• Minimum 1 year of management or supervisory experience
• Ability to lead teams in a high-volume, fast-paced environment
• Strong communication, organization, attention to detail and problem-solving skills
• Guest-first mindset with a positive and solutions-oriented attitude
• Ability to balance hands-on service with operational leadership
• Reliable transportation and ability to commute to Bolton, MA (Required)

• Employee discount
• Tipped position
• Day shifts (8–10 hours)