Part-Time Wine Experience Assistant
The Sweet Cheeks Winery family is an extension of the legacy built by our founder, Dan Smith. Our tasting room team fully embraces a hospitality-driven and elevated wine-focused experience with every guest — we always strive to be the best part of their day. Our Southern Willamette Valley winery is looking for Wine Experience Assistants to support our Wine Educators and Hosts in executing seamless, thoughtful guest experiences.
This position is integral to keeping service flowing smoothly, ensuring each section is reset, supported, and ready for the next guest experience.
To Set the Scene
- This position works closely with Wine Educators, Hosts, and Bussing/Food Prep team members.
- You will be assigned to support a designated section of the tasting room during service.
- Sweet Cheeks Winery is not a restaurant, but an operating vineyard and winery selling its direct products.
- You will work both independently and as part of a collaborative team.
- This is a physically active role requiring standing, walking, lifting, and communication for extended periods.
- This role is designed as a growth position, offering hands-on exposure to wine education, service flow, and guest engagement.
What Qualities Are We Looking For?
- A genuine passion for hospitality and creating seamless guest experiences.
- Strong awareness and attention to detail — you notice what needs to be done before being asked.
- Ability to anticipate the needs of Wine Educators and guests.
- Naturally friendly, calm, and professional demeanor.
- Strong desire to learn about wine, service strategy, and guest engagement.
- Ability to listen, observe, and adapt quickly in a fast-paced environment.
- Team-oriented mindset with a willingness to jump in wherever needed.
Skills and Abilities Required
- Must be 20+ to apply.
- Prior hospitality or restaurant experience is preferred but not required.
- Ability to multitask while staying organized.
- Excellent communication skills.
- Able to follow systems and standards consistently.
- Comfortable working in a fast-paced environment.
- Must adhere to dress code standards consistent with company expectations.
- Must be able to stand and walk for extended periods (6–8 hours).
- Must be able to lift 40–50 lbs regularly.
- Must have, or be willing to obtain, an Oregon Food Handler Card and OLCC permit.
Essential Duties & Responsibilities
- Support Wine Educators during service to ensure experiences run smoothly and on pace.
- Maintain water service for guests, ensuring glasses are refreshed and tables are attended to.
- Assist with running food items to tables accurately and in a timely manner, ensuring correct plates, utensils, and presentation.
- Reset tables promptly between guests, ensuring cleanliness and presentation meet company standards.
- Stock and maintain necessary service items including glassware, water, utensils, menus, and food service supplies.
- Communicate proactively with Hosts regarding table readiness and section flow.
- Assist with polishing glassware and maintaining cleanliness of service areas.
- Observe Wine Educators during guest interactions to learn wine knowledge, pacing strategies, and hospitality techniques.
- Watch for signs of intoxication and communicate concerns to management or Wine Educators as needed.
- Follow all Sweet Cheeks Winery values, hospitality standards, OLCC regulations, and safety guidelines.
- Perform additional duties as assigned by Managers.
Schedule
- Part-time position; minimum availability of 16 hours per week.
- Typical shifts are 6–8 hours between 10am–6pm.
- Weekend and holiday availability is required; weekday availability is a plus.
- Schedule posted at least one week in advance.
Compensation
- Hourly position starting at $15.25/hour.
- Eligible for gratuity after training.
Advancement Opportunities
This role is designed as a stepping stone within the tasting room team. Wine Experience Assistants are encouraged to grow into Host or Wine Educator positions through demonstrated performance, product knowledge, and hospitality excellence. Advancement opportunities are available after a minimum period of employment, pending business needs and application.
How to Apply
Please send your resume and cover letter directly to courtney@sweetcheekswinery.com. In your cover letter, please include:
- What appeals to you about this position
- Your interest in hospitality and wine
- Any applicable experience
What to Expect
- Resumes and cover letters are reviewed by the hiring committee.
- Interviews are extended to those who meet minimum qualifications and are held on-site.