Retail & Experience Supervisor - Tasting Room

If you love hospitality, enjoy connecting with people and are ready to take the next step in your career, this is an opportunity to grow your leadership experience in a unique winery environment.

As Retail and Experience Supervisor, you’ll be part of creating memorable guest experiences through wine tastings, tours, retail, Wine Club and special events. You’ll work alongside an experienced Retail & Experience Manager while gaining exposure to the many facets of winery tourism and direct-to-consumer business.

This is a hands‑on role for someone who enjoys being part of a team, leading by example and making every guest interaction count.

• Support and supervise the Tasting Room team, helping create a positive and high‑performing team environment.
• Deliver exceptional guest experiences through tastings, tours and knowledgeable wine recommendations.
• Lead group tours and support the delivery of special events and Scenic Sip Wine Trail activations.
• Support retail and Wine Club sales and help the team achieve revenue targets.
• Assist with staff scheduling, daily task assignments, coaching and team performance.
• Maintain engaging retail merchandising, seasonal décor and product presentation.
• Coordinate group bookings and ensure a seamless experience for guests across the winery and restaurant.
• Develop strong knowledge of current and library wines, tours, restaurant offerings and Wine Club benefits.
• Manage Wine Library inventory and support retail inventory, receiving and stocking.
• Coordinate direct‑to‑consumer wine orders, including pick, pack and shipping.
• Support day‑end cash reporting and ensure retail operations follow established procedures.
• Maintain a clean, safe and welcoming environment for guests and team members.

• 2+ years of experience in retail, hospitality, tourism, customer service or a related environment, with supervisory or team leadership experience preferred.
• Experience in a winery, hospitality, tourism or premium retail environment is an asset.
• A genuine interest in wine and creating exceptional guest experiences.
• Strong communication and interpersonal skills.
• An outgoing, enthusiastic and professional approach.
• The ability to stay calm, organized and positive in a fast‑paced environment.
• Strong multitasking and problem‑solving skills.
• Comfort using technology, POS and scheduling systems; experience with LS Retail or Dayforce is an asset.
• Wine education such as WSET, ISG/CAPS or CMS is an asset.
• Availability to work evenings, weekends and holidays as required.

Most importantly, we’re looking for someone who is curious, eager to learn and ready to grow their leadership skills while helping our guests have an extraordinary experience.