Side Saddle Wine Saloon is a neighborhood restaurant, wine bar, and gathering place built around thoughtful food and drinks, genuine hospitality, and a welcoming, energetic environment. We operate in a Team Service Model.
We believe great hospitality should feel personal, knowledgeable, inclusive, and fun. We’re looking for Servers who genuinely enjoy taking care of people, work well as part of a team, and want to create an experience that keeps guests coming back.
The Role
Servers are at the center of the Side Saddle guest experience.
You’ll guide guests through our food, wine, cocktail, beer, coffee, and non-alcoholic offerings while providing warm, attentive service. We want servers who can read a table, make thoughtful recommendations, stay organized when things get busy, and understand that hospitality is about much more than taking an order.
Side Saddle is a team environment. Everyone runs food, clears tables, resets the space, supports their coworkers, and takes responsibility for the overall guest experience.
What You’ll Do
Hospitality & Service
- Welcome guests warmly and create a comfortable, engaging experience.
- Guide guests through our food and beverage menus and confidently make recommendations.
- Take accurate orders and communicate modifications, allergies, and dietary restrictions appropriately.
- Maintain awareness of your entire section and anticipate guest needs.
- Check in thoughtfully without interrupting the guest experience.
- Resolve smaller guest concerns and quickly involve a manager when additional support is needed.
- Build relationships with regulars and contribute to the neighborhood atmosphere Side Saddle is known for.
- Help guests celebrate everything from an everyday glass of wine to birthdays, dates, and special occasions.
Food & Beverage Knowledge
- Develop strong knowledge of our food, wine, cocktails, beer, coffee, and non-alcoholic offerings.
- Participate in tastings, menu education, and pre-shift meetings.
- Learn how to describe wine and food in a way that is approachable rather than intimidating.
- Make thoughtful recommendations based on guest preferences.
- Understand menu ingredients, common allergens, and available modifications.
- Practice responsible alcohol service at all times.
Teamwork & Operations
- Run food and beverages for your own tables and your teammates.
- Clear, clean, and reset tables throughout service.
- Complete opening, running, and closing side work thoroughly.
- Maintain clean and organized service stations and guest areas.
- Communicate clearly with bartenders, kitchen staff, support staff, and managers.
- Support private events, weekly programming, brunches, and high-volume services.
- Follow all cash-handling, POS, tip, discount, and checkout procedures.
- Arrive on time, prepared, and ready to contribute to the shift.
Who We’re Looking For
You may be a great fit if you:
- Genuinely enjoy hospitality and taking care of people.
- Are warm, confident, and comfortable talking with a wide range of guests.
- Can stay organized and positive during busy services.
- Take initiative instead of waiting to be asked.
- Communicate clearly and respectfully with teammates.
- Understand that no task is beneath you when it helps the team or guest.
- Are interested in wine, cocktails, coffee, and food and excited to continue learning.
- Are reliable and take your schedule and commitments seriously.
- Are comfortable working evenings, weekends, holidays, and high-volume events.
- Have previous restaurant experience. Wine or bar experience is a plus, but curiosity and willingness to learn matter just as much.
What Success Looks Like
A successful Side Saddle Server:
Makes guests feel genuinely welcomed.
Knows the menu and can confidently guide the experience.
Notices what needs to happen before being asked.
Supports the entire floor—not just their own section.
Communicates well with both FOH and BOH.
Is reliable, prepared, and accountable.
And helps create the kind of experience that turns first-time guests into regulars.
Side Saddle Wine Saloon is a women-owned neighborhood wine bar created to bring people together over thoughtfully selected wines, warm hospitality, and meaningful connection. Founded by entrepreneur and community builder Kayla Bellman, Side Saddle was built on the belief that great wine should feel approachable, welcoming, and accessible to everyone.
Drawing on her experience creating community through Finca to Filter, Kayla envisioned a space where guests could discover new wines, gather with friends, and enjoy memorable experiences in a relaxed, inviting atmosphere. Side Saddle blends a modern wine program with the spirit of a neighborhood gathering place, a destination for both seasoned wine enthusiasts and those just beginning their wine journey.
Benefits
Tips
Job Type
Full time, Part time
Schedule
Weekend availability, Holidays, Monday to Friday, Day shift, Night shift, 8 hour shift