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Bartender and Event Operations Lead - Weekday/Corporate

Posted: 08/05/2026

Bar, Beverage and Catering Service

Chesapeake Bartenders and Events | Stevensville, MD (Kent Island) Part time, W2 employee | Approximately $400 per event 


About the role

We run a high-end bar, beverage and light bites catering service for corporate events in Washington DC, Baltimore, Annapolis and across the Eastern Shore. Think law firms, financial firms, brand activations and company parties. We have been doing this since 2019 and we have a roster of repeat clients who ask for us by name.

This role is our weekday corporate person. You load equipment at our Kent Island office, pick up supplies on your way, set up on site, run service for a couple of hours, break down and head home. Most days are under eight hours door to door.

The ideal candidate is a great, polished hospitality professional who can set up a beautiful mobile bar and be a fantastic bartender for luxury-tier events and clients. Depending on the event you might be running:

  • Full bar service with cocktails, beer and wine
  • Mocktail Service
  • Non alcoholic beverage stations
  • Coffee and espresso service
  • Charcuterie and antipasto displays
  • Fruit, pastry and light bites setups

Some events are all of the above. Some are just coffee and a charcuterie board for a morning meeting or lunch and learn.

We are not a staffing agency that drops a body behind someone else's bar. We bring our own equipment, our own setup and our own standards, and you would be the person carrying that. A big part of the job is making the table look as good as the drinks taste. We provide extensive SOP's with visual guidance and hands on training. 


Pay

$400 per event, flat. Not hourly. Not a shift rate you have to do math on.

That $400 covers the whole job: loading at the office, any supply pickups on the way, drive time to and from DC, Baltimore or wherever the event is, setup, up to four hours of service, breakdown and load out. It is broken down on your pay stub as $250 bartending, $50 automatic gratuity and $100 delivery and mileage, but the number you need to remember is $400.

Guest tips are yours on top of that. Longer or larger events pay more.

For scale, a typical day looks like a 1:00 PM start at the office, service from 5:00 to 7:00, and unloaded by 8:30pm. 


Schedule

Events fall Monday through Friday. Start times vary a lot. Some events are morning setups for lunch service, some are evening happy hours. There is no fixed pattern, which is why this role does not work for someone already holding a Monday through Friday job.

There is seasonality, and September - December are by far, our busiest months. You might do 1 - 3 events per week based on former year event executions.


What we need from you

  • You live on the Eastern Shore or in the Annapolis area, close enough to our Stevensville office to load equipment/supplies. 
  • A reliable vehicle that can carry two six foot folding tables, small coolers and bar equipment. An SUV is ideal. A truck, van or car also works. Reliable matters as much as roomy, because a lot of this job is arriving on time with everything.
  • A clean driving record and a valid license.
  • A clean background check - we often have to get security clearances to be on site at some of our event locations.
  • You are available during weekday business hours. No conflicting full time job.
  • You can lift and move equipment. Coolers with ice get heavy.
  • You are comfortable handling food. Some events involve platters, displays and light assembly on site.
  • You communicate immediately when something goes wrong. Cars break down and traffic happens. We can solve almost anything with enough notice and almost nothing with none.
  • TIPS Certification - you must be TIPS Certified within 2 weeks of being hired 
  • ServSafe Food Handler Certification - CBE will pay for the course and exam - certification must be awarded within 2 weeks of being hired.
  • Access to a reliable computer with internet service - must be able to communicate via email with operations and leadership team during business hours.
  • A clean appearance - long hair tied back, clean, wrinkle-free clothing, great hygiene

Ideal Candidate and Experience

  • Bartending, catering, hospitality or food service experience
  • Reliable, great communicator, self-starter, punctual, polished
  • Loves learning and delivering an unparalleled guest experience
  • Good at holding conversations with clients (a must!)
  • Comfort building a food display that looks good, not just tastes good
  • An eye for presentation. Our clients notice the styling as much as the service
  • Barista, Banquet Coordinator, Smoothie Bar Operator - these positions are a great starting point and have similar service paces
  • Can commit to 2 events per week during busy season

We have trained people with zero bar experience into some of our best staff. Reliability and attention to detail matter more to us than a resume.


Why people like working here

  • Real pay for real hours, no waiting around for a slow shift to fill your night
  • You are treated like a professional, not a warm body
  • Small team, direct access to the owner, no layers
  • Genuinely fun work with good clients and good people
  • Fun and inspiring work environments - we work with some amazing and well-known clients who value our service and expertise
  • Opportunity for growth - there are more shifts and opportunities on weekends for weddings and private parties if you enjoy this role and want to take on more shifts
  • You know how much you will make regardless of how busy it is - no getting cut early because there are not many customers. Your pay is $400 per event, unless otherwise noted for increased/decreased scope
  • Variety - you get to lead a lot of fun events on Capital Hill, for financial firms, for tech companies, etc. 

To apply

Send a short note telling us:

  1. Where you live and what vehcile you drive
  2. Your weekday availability
  3. Any hospitality, event, catering or customer service experience
  4. Tell us about a time something went wrong at work and what you did about it
  5. Why are you a great fit for this position
  6. Three Professional References (cannot be from a family member)
  7. What do you think the most important part of delivering an amazing hospitality experience is? 
  8. What is your favorite drink to make and why?

Please send to courtney@chesapeakebartenders.com with the following subject line:

Bartender and Event Operations Lead - Weekday/Corporate