1000+ Best pay weekly Jobs in Philadelphia, Pennsylvania (March 2026) - page 10

Wine Captain / Head Server

2 days ago

Wayne

Job Title Wine Captain / Head Server Hours/Week Full Time Tuesday–Saturday; closed Sunday & Monday Evening and weekend availability required Location 1 West Ave. Wayne, PA Pay Rate Full Time • Hourly & Salary (after 6 months) + Service Compensation (Based on Experience) Competitive compensation package Expected income of $115K–$135K+ annually depending on experience and performance Position Opportunity Cornerstone is seeking an experienced and hospitality-driven Wine Captain / Head Server to play a leadership role in our front-of-house team and wine program. Founded and operated by chef-owners Christine & Nick Kondra since 2015, Cornerstone has become one of the most sought-after restaurants in the Philadelphia area. Over the past decade, we have built a reputation for exceptional guest experiences paired with an award-winning wine and cocktail program. Recognized regionally and nationally by Wine Spectator, and with Christine Kondra honored as Best Sommelier on the Main Line of Philadelphia, Cornerstone continues to evolve while staying grounded in thoughtful, intentional hospitality. This role offers a rare opportunity to work closely alongside Christine Kondra and one of the region’s most respected wine programs, featuring a cellar of over 1,200 carefully curated bottles from around the world. The Wine Captain will play an active role in presenting and representing this program to guests, helping translate the depth of the collection into meaningful and memorable dining experiences. This position will play a key role in delivering the Chef’s Counter experience, working closely with ownership and the culinary team to provide an immersive, highly personalized guest journey. The ideal candidate is an experienced server with strong wine knowledge and sommelier-level hospitality instincts, capable of guiding guests through pairings, storytelling, and refined service. This is an exciting opportunity for a hospitality professional who thrives in a luxury dining environment, enjoys engaging guests through wine and cuisine, and wants to grow within a thoughtful, globally inspired dining program. The Philosophy Behind the Cornerstone Program At Cornerstone, growth and curiosity are foundational. Christine & Nick Kondra have spent over a decade refining their craft, drawing inspiration from years working with chef-owners in Boston and traveling internationally to explore the world’s leading restaurants, wineries, and hospitality cultures. That exploration continues to shape every aspect of the Cornerstone experience. Our service philosophy emphasizes precision, education, and storytelling — connecting guests not only to the food and wine on the table, but to the people, places, and traditions behind them. The Wine Captain plays an essential role in this experience. At the Chef’s Counter especially, service becomes a conversation — guiding guests through the evening, presenting wines with context and enthusiasm, and ensuring that every moment feels thoughtful, seamless, and memorable. This role requires a balance of technical wine knowledge, polished service execution, and natural hospitality leadership. We are seeking someone who takes pride in excellence, values continuous learning, and is energized by the opportunity to elevate every guest interaction. Position Summary The Wine Captain / Head Server is responsible for delivering exceptional service while leading wine engagement on the floor. This role supports the restaurant’s wine program through guest education, thoughtful pairings, and polished table-side presentation. Working closely with ownership and the service team, the Wine Captain helps maintain the standards of Cornerstone’s hospitality while ensuring guests feel guided, welcomed, and inspired throughout their dining experience. Essential Duties & Responsibilities Guest Experience & Service Leadership • Provide refined, attentive service aligned with Cornerstone’s hospitality standards., • Guide guests through multi-course dining experiences, particularly at the Chef’s Counter., • Create engaging and educational interactions around wine, food pairings, and menu components., • Serve as a primary ambassador of the wine program on the dining room floor., • Assist guests with wine selections and pairing recommendations., • Confidently present wines with knowledge of region, producer, varietal, and style., • Support wine service standards including proper opening, decanting, and presentation., • Serve as a senior service professional within the front-of-house team., • Support training and mentorship of newer servers in service standards and wine knowledge., • Work collaboratively with the kitchen to ensure seamless Chef’s Counter experiences., • Inventory control and management - weekly and monthly, • Assist with opening and closing service responsibilities., • Maintain organization and accuracy within the wine cellar and service stations., • Ensure glassware, decanters, and wine tools are properly prepared and maintained., • Help uphold presentation and hospitality standards across the dining room. Experience Minimum 5 years of serving experience in upscale or fine dining restaurants required. Additional preferred experience: • Fine dining, private clubs or luxury restaurant environments, • Chef’s counter or tasting menu service, • Wine-focused restaurants or sommelier-led programs, • Sommelier certification or formal wine education Skills • Advanced hospitality and service instincts, • Strong foundational wine knowledge - Certified Sommelier preferred, • Confident tableside communication and storytelling, • Ability to anticipate guest needs and manage service pacing, • Strong teamwork and leadership presence on the floor Knowledge • Understanding of wine regions, varietals, producers, and pairing principles, • Familiarity with fine dining service techniques and tasting menu flow, • Knowledge of proper wine service including decanting, storage, and presentation Attributes • Warm, confident, and engaging with guests, • Detail-oriented and committed to service excellence, • Passionate about food, wine, and hospitality culture, • Calm and composed in a fast-paced environment, • Curious and eager to continue learning and growing in wine and service Working Conditions Environment Fast-paced, high-end restaurant environment requiring evening, weekend, and holiday availability. Physical Demands • Ability to stand for extended periods during service., • Ability to carry trays, handle wine service equipment, and move throughout the dining room., • Ability to lift up to 30 lbs as needed. Benefits & Perks • Health Insurance, • Dental Insurance, • Vision Insurance, • Paid Time Off, • Dining Discounts, • Wellness Program ($65 per month), • Professional Enrichment Program ($100 per month), • Voluntary Benefits including disability, long-term care, cancer, and life & accident Cornerstone is seeking a Wine Captain who views hospitality as both craft and performance — someone who enjoys connecting with guests, sharing the story behind exceptional wines, and helping create unforgettable dining experiences. To be considered for the position please provide both your resume and cover letter.

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