Server, Server​/Wait Staff

Kissimmee, Florida | Family-Owned Since 1999

Full-Time & Part-Time | Competitive Pay + Tips | Immediate Openings

For 25 years, Woodsby's Cafe has been a cornerstone of the Kissimmee community — a family-owned restaurant where neighbors become regulars, and regulars become family. We've earned three consecutive local awards for Best Breakfast, Best Burger, and Best Home Cooking in Osceola County, and we take that responsibility seriously every single day.

Our 82-seat dining room is warm, welcoming, and built on a foundation of genuine hospitality. We serve breakfast, lunch, and dinner seven days a week, with rotating daily specials that keep our guests — and our team — excited. If you love great food, love people, and love being part of something that truly matters to your community, you'll feel right at home here.

Mon–Fri: 7am–7:30pm
Sat–Sun: 7am–8pm

Breakfast, Lunch, Dinner
Specials, Apps & Desserts

Kissimmee, FL
(Osceola County)

As a server at Woodsby's, you are the heart of the guest experience. You'll guide tables from warm welcome to satisfied farewell — taking accurate orders, sharing your knowledge of our menu and daily specials, and ensuring every guest feels like the most important person in the room. Our servers are trusted team members who contribute to a kitchen running smoothly and a dining room that runs even better.

• Guest
  
  Experience:
  
  Greet guests warmly, take accurate orders, and create a memorable dining experience from the first hello to the final thank-you.
• Menu Mastery: Know our full menu — breakfast, lunch, dinner, daily specials, soups, appetizers, and desserts — and confidently guide guests through it.
• Allergy & Dietary Awareness: Communicate clearly about ingredients and allergens; involve a manager for complex dietary needs and prioritize guest safety above all else.
• Upselling & Recommendations: Suggest specials, appetizers, beverages, and desserts naturally and genuinely to enhance the guest experience and support the team's performance.
• Order Accuracy: Enter all orders correctly into our Shift4 POS system; double-check before sending to the kitchen to reduce errors and re-fires.
• Wait Time Communication: Set honest expectations during busy periods, keep guests informed, and help manage the flow of the dining room alongside the front-of-house team.
• Team
  
  Collaboration:
  
  Work closely with kitchen staff, the FOH manager, and fellow servers to keep service moving smoothly during peak breakfast and weekend rushes.
• Cleanliness & Standards: Maintain a clean table, station, and dining area throughout each shift; follow all health and safety protocols.
• Scheduling: Use 7
  
  Shifts to view schedules, confirm availability, and coordinate shift coverage.

• Genuine warmth and a hospitality-first mindset
• Ability to stay calm, organized, and positive in a fast-paced, high-volume environment
• Strong communication skills — with guests, teammates, and kitchen staff
• Reliable availability, including weekends and some holidays
• Comfort working on your feet for a full shift
• Team player attitude — we succeed together or not at all

• 1+ year of serving or front-of-house experience in a full-service restaurant
• Familiarity with Shift4 POS or a comparable point-of-sale system
• Experience using 7
  
  Shifts or similar scheduling software
• Basic food safety and allergen awareness knowledge
• Comfort with upselling and making genuine recommendations

Award-Winning Reputation. Guests come to us because we've earned their trust. You'll serve food and an experience that people genuinely love — that makes the job feel meaningful.

Family Culture. We're a tight-knit team of 24 where everyone looks out for each other. Our managers are in the trenches with you, not just watching from the sideline.

25 Years of Community. We're not a chain. We're a neighbor. Our regulars are real people who come back three times a week because they feel at home here — and so will you.

Consistent Hours, Great Tips. We're open seven days a week with predictable shift windows. Our average check runs $17–$19 across meals, and our loyal regulars are generous tippers.

Room to Grow. We invest in people who invest in us. If you want to move into a lead or management role, we'll help you get there.