Job Description

We’re looking for enthusiastic, fun, and energetic people who take the work seriously, but not themselves. Let’s see if we’re a fit. We hope so.

About the Fenway Hotel
Originally opened in 1927, The Fenway Hotel is an icon of the jazz age, playing host to notable explorers, artists, politicians, musicians and living legends in its time as an operating hotel. Today, Fenway is a Mainsail Lodging & Development hotel and a member of the prestigious Autograph Collection® of Marriott International, Inc.

The Fenway Hotel overlooks the beautiful Dunedin Channel offering views of breathtaking sunsets and gorgeous Florida waters. This Historic Jazz inspired property has created a homage to Dunedin’s rich music history and a destination for those to get carried away in their own verse. If you share our passion, we look forward to hearing from you.

It’s time to write your own tune with us and join the band at Dunedin’s very own jazz inspired boutique hotel. Can you sing along? Apply today!

Tampa Bay Top Workplaces

“Voted a Top Workplace! Mainsail Lodging & Development was named a 2025 Top Workplace by the Tampa Bay Times—a reflection of our positive culture, growth opportunities, and commitment to our team. Join us!”

The Server is responsible for delivering exceptional food and beverage service by creating memorable dining experiences through attentive, knowledgeable, and professional hospitality by performing the proper steps of service. This role ensures accurate order delivery, maintains a thorough understanding of menu offerings, promotes sales through suggestive selling and beverage pairings, and upholds all service, safety, sanitation, and responsible alcohol service standards.

The Server works collaboratively with culinary and management teams to provide seamless service, promptly addresses guest concerns, maintains dining room cleanliness and presentation, and contributes to a welcoming environment that reflects the highest standards of guest satisfaction.

The Server will do this in a manner and practice that ensures exceptional service to all guests and is consistent and continually in accordance with the Marriott Autograph Collection standards under the franchise of Mainsail Lodging & Development.

Essential Job Functions

• Serve meals to the guest in a professional and hospitable manner, following the proper steps of service
• Ensure drinks and meals are delivered to the correct recipient with allergies and specific requests in mind
• Engage guests with a welcoming, knowledgeable, and energetic presence
• Set up tables with items needed for service in compliance with established guidelines for proper placement (i.e. flatware, drinkware, condiments, linens, etc.)
• Ensure tables and seating areas are thoroughly cleaned, sanitized, and free of debris, spills, and crumbs to maintain a clean and welcoming dining environment for guests
• Maintain knowledge of current menu items, including ingredients, preparation, accompaniments, and sauces
• Follow cash handling policy and procedures, ensuring there is an explanation for any shortages and overages
• Upsell menu items and drinks to guests, as well as appropriately pairing wine variations with the meal
• Bus tables quickly and quietly, ensuring tables are thoroughly cleaned and sanitized
• Ensure guest tables are properly set up, making sure appropriate flatware and drinkware is placed
• Participate in daily cleaning and weekly deep cleaning of dining room and service stations
• Address customer concerns or complaints calmly and promptly and keep management informed of any issues negatively impacting the guest experience
• Follow all safety protocols for both work related injuries and guest incidents
• Follow TIPS practices to ensure safe and responsible serving of alcohol, including following local laws regarding alcohol consumption and checking validity of age
• Collaborate with management and culinary staff to ensure timely and seamless service for food and beverage items
• Attend required department meetings and daily standups
• Continually train on new products and recipes, especially when seasonal menu offerings change
• Report to work punctually, well-groomed, and in appropriate attire
• Collaboratively and positively work with other team members in assisting with running food, bar support and cross training
• Actively participate and maintain running side work throughout the scheduled shift
• Available to work both morning and evening shifts to support operational needs, with schedules determined by business needs, skill proficiency, employment status and tenure
• Other necessary duties as reasonably assigned

Hotel Performance

• Ensure successful performance by assisting guests with an exceptional experience to ensure high performing scores on the GSS (Guest Satisfaction Surveys) according to Marriott and Mainsail/Fenway standards

Education & Experience

• High School Diploma or higher
• Previous server experience in a fine dining restaurant required
• Prior hospitality and/or hotel serving experience preferred
• Excellent customer service skills
• Excellent communications skills
• Ability to use technology to include computers, tablets, POS and iPads
• Working knowledge of food and beverages
• Knowledge of local laws regarding serving and consumption of alcohol
• Wine certifications: Court of Master Sommelier, WSET, SWE ect.. is a plus
• Food certifications: TIPS, Food handling is a plus.

Physical Demands

• Ability to sit or stand for extended periods of time
• Ability to bend frequently
• Ability to lift, push, pull up to 50 lbs
• Ability to communicate clearly
• Corrected vision to normal range
• Ability to work long hours as needed

Mental Demands

• Make sound judgments quickly
• Work on multiple tasks, making appropriate progress towards deadlines
• Able to work independently, take direction, and provide direction to others
• Manage differing personalities within the office, the hotel, and the community
• Maintain the highest degree of confidentiality
• Ability to work effectively in stressful, high-pressure situations
• Ability to effectively handle challenges in the workplace, including anticipating, preventing, identifying, and solving problems as necessary

NOTICE: The hotel business functions seven days a week, 24 hours a day. All associates must realize this fact and be aware that at all times it may be necessary to move associates from their accustomed shift as business demands. In addition, this is a hospitality business and a hospitable service atmosphere must be projected at all times.

Benefits

Full-time Associate Benefits

• Medical, Dental, & Vision | HSA & Flexible Spending Account Options | Basic Life & Disability Plan Options | 401K Retirement Plan | Paid Time Off | Holiday Pay | Career Training & Development Opportunities | Tuition Reimbursement | Bereavement Leave | Employee Assistant Program (EAP) | Jury Duty (May vary by state) | Employee Discounts | Employee Referral Bonus | Free meal for all full-service hotel employees

Part-time Associate Benefits

• All above-listed benefits except for Medical Insurance, Holiday Pay, Tuition Reimbursement

Mainsail is an Equal Opportunity Employer and it does not discriminate on the basis of actual or perceived race, color, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity expression (including transgender status), sexual orientation, marital status, parental status, military service and veteran status, political affiliation, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances.