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Server Winter Jobs in Wisconsin (NOW HIRING)

Nakoma Golf Club Inc

Server

Madison, WI · On-site

$12/hr

Reservation taking We are seeking a skilled server to join our team at Nakoma Golf Club. The ideal ... the winter, and shuts down completely for 3-4 weeks in February. Extensive food and beverage ...

Nakoma Golf Club Inc

Server Assistant

Madison, WI · On-site

$14/hr

Reservation taking We are seeking a skilled server assistant to join our team at Nakoma Golf Club ... during the winter, and shuts down completely for 3-4 weeks in February, Previous restaurant ...

Nakoma Golf Club Inc

Server Assistant

Madison, WI · On-site

$14/hr

Reservation taking We are seeking a skilled server assistant to join our team at Nakoma Golf Club ... during the winter, and shuts down completely for 3-4 weeks in February, Previous restaurant ...

Western Racquet Club

Seasonal Bartender

Elm Grove, WI · On-site

$15 - $18/hr

... winter season. This position offers the opportunity to work in a variety of club settings ... Must maintain a Responsible Beverage Server Certificate. * Must be 18+ and certified to serve ...

Compass Group

CAPTAIN, CATERING SR

Whitewater, WI · On-site

$24/hr

Must possess or able to obtain a valid food handler's permit and/or alcohol servers permit where ... as winter and summer breaks when food service needs decline or cease). Any such periods during ...

Compass Group

CAPTAIN, CATERING SR

Whitewater, WI

$24/hr

Must possess or able to obtain a valid food handler's permit and/or alcohol servers permit where ... as winter and summer breaks when food service needs decline or cease). Any such periods during ...

Chartwells HE

CAPTAIN, CATERING SR

Whitewater, WI

$24/hr

Must possess or able to obtain a valid food handler's permit and/or alcohol servers permit where ... as winter and summer breaks when food service needs decline or cease). Any such periods during ...

Chartwells HE

CAPTAIN, CATERING SR

Whitewater, WI · On-site

$24/hr

Must possess or able to obtain a valid food handler's permit and/or alcohol servers permit where ... as winter and summer breaks when food service needs decline or cease). Any such periods during ...

Compass Group

CATERING CAPTAIN

Waukesha, WI · On-site

$17/hr

Must possess or able to obtain a valid food handler's permit and/or alcohol servers permit where ... as winter and summer breaks when food service needs decline or cease). Any such periods during ...

Compass Group

CAPTAIN, CATERING SR

Whitewater, WI · On-site

$24/hr

Must possess or able to obtain a valid food handler's permit and/or alcohol servers permit where ... as winter and summer breaks when food service needs decline or cease). Any such periods during ...

Compass Group

CATERING CAPTAIN

La Crosse, WI · On-site

$22/hr

Must possess or able to obtain a valid food handler's permit and/or alcohol servers permit where ... as winter and summer breaks when food service needs decline or cease). Any such periods during ...

Compass Group

CATERING ATTENDANT

Superior, WI · On-site

$16.48/hr

... servers' permit where required by state law. The Benefits We are always looking for ways to invest ... as winter and summer breaks when food service needs decline or cease). Any such periods during ...

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All JobsServer Winter JobsServer Winter Jobs in Wisconsin

Server Winter information

What jobs pay 4000 a week without a degree?

Server positions in high-end restaurants or private clubs can sometimes pay $4,000 or more weekly through tips and base wages, especially with experience and busy shifts. Other high-paying roles without a degree include sales, real estate, or skilled trades like plumbing or electrical work, which rely on skills and certifications rather than formal education.

What's a good winter job?

A server position is a popular winter job, especially in restaurants and cafes that experience increased holiday and winter season traffic. It typically requires good customer service skills, the ability to work in a fast-paced environment, and may involve working evenings and weekends. Seasonal server jobs can provide flexible hours and tips during busy winter months.

What are Server Winters?

A Server Winter is a hospitality worker who serves food and beverages to guests, specifically during the winter season at resorts, lodges, or restaurants in winter destinations. Their responsibilities include taking orders, delivering meals, ensuring guest satisfaction, and sometimes handling payments. Server Winters often work in ski resorts, mountain lodges, or other venues that experience peak business during the colder months. This seasonal role requires excellent customer service skills and the ability to work in fast-paced environments.

What is the difference between Server Winter vs Server Summer?

AspectServer WinterServer Summer
CertificationsFood Handler Permit, Alcohol Service CertificationFood Handler Permit, Alcohol Service Certification
Work EnvironmentIndoor, colder months, slower seasonIndoor, warmer months, peak season
Industry UsageOff-season staffing, seasonal rolesPeak season staffing, high customer volume

Server Winter and Server Summer roles share similar certifications and work environments but differ mainly in seasonal demand. Server Winter typically involves off-season work with lower customer volume, while Server Summer is associated with peak season, higher tips, and busier shifts. Understanding these differences helps job seekers choose roles aligned with their seasonal availability and career goals.

What are some unique challenges servers face during the winter season at resorts or ski lodges?

Servers working in winter resort settings often experience high guest volumes during peak holiday times, which can lead to fast-paced shifts and increased pressure to deliver excellent service. Additionally, navigating icy or snowy conditions—both outside and sometimes inside—can make transporting food and drinks more challenging. Teamwork is crucial, as servers must coordinate with kitchen staff and fellow servers to manage large groups and special events typical of the winter season. Flexibility with scheduling is also important, as demand can fluctuate with weather and holiday bookings.

Can you make $100,000 as a server?

Earning $100,000 annually as a server is possible but uncommon and typically requires high tips, extensive experience, working in high-end establishments, or multiple shifts. Most servers earn a combination of base pay and tips, with total income varying widely based on location, hours worked, and customer volume.

What are the key skills and qualifications needed to thrive as a Server in a winter seasonal setting, and why are they important?

To thrive as a Server in a winter setting, you need strong customer service skills, basic food and beverage knowledge, and often previous experience in hospitality. Familiarity with point-of-sale (POS) systems and, in some cases, alcohol serving certifications are typically required. Outstanding interpersonal skills, teamwork, and the ability to remain calm under pressure help servers deliver exceptional guest experiences during busy peak seasons. These abilities are crucial for maintaining efficient service and positive client relations in high-demand winter resort or restaurant environments.

What jobs can I get after being a server?

After working as a server, common job options include roles in hospitality such as bartender, host, or catering staff, as well as customer service positions in retail or call centers. Skills gained as a server, like communication, multitasking, and handling customer needs, are valuable in many service-oriented jobs and can help in career advancement or transitioning to management roles.
What are popular job titles related to Server Winter jobs in Wisconsin? For Server Winter jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Server Winter jobs in Wisconsin look for? The top searched job categories for Server Winter jobs in Wisconsin are:
What cities in Wisconsin are hiring for Server Winter jobs? Cities in Wisconsin with the most Server Winter job openings:
Server Winter jobs near you
Infographic showing various Server Winter job openings in Wisconsin as of July 2026, with employment types broken down into 100% Part Time. Highlights an 100% In-person job distribution.
Server

Server

Nakoma Golf Club Inc

Madison, WI • On-site

$12/hr

Part-time

Posted 4 days ago

Job description

Skills:

  • Food knowledge
  • Beverage knowledge
  • Wine service
  • Hospitality focused
  • Steps of service
  • Cash Handling
  • Multitasking
  • Awareness
  • Team player
  • Organized
  • Attention to detail
  • Event serving
  • Event set up and breakdown
  • Answering Phones
  • Reservation taking

We are seeking a skilled server to join our team at Nakoma Golf Club. The ideal candidate will have experience in serving, event serving, event setup & breakdown, phone reception, and reservation taking. A willingness to cross-train in other positions is a plus. Weekend and holiday availability are required to be considered for this position, and all staff are required to be available to work at least 3 shifts per week. Please note that the clubhouse is closed on Mondays (unless there is a golf outing scheduled), reduces a few services during the winter, and shuts down completely for 3-4 weeks in February.

Extensive food and beverage knowledge is a plus, but a willingness to learn and ask questions is extremely important. We prioritize initiative over knowledge. Prior experience in Country Clubs is a plus, but not necessary. Bartending experience is also a plus, but not necessary.

You should understand the basic steps of service, have solid spatial awareness, be a team player, be able to maintain organization, have high attention to detail, and an understanding of exceptional hospitality.

If you are passionate about providing excellent customer service and have the skills we are looking for, we encourage you to apply.

Base wage is $12 per hour plus tips. Event wage is $16 per hour (additional tips are possible, depending on the event).

Must be 18+ to apply.