Position Overview:
We’re looking for a Tasting Room & Operations Associate who enjoys spending time with guests in the tasting room just as much as keeping things running smoothly behind the scenes. This is a true 50/50 hospitality and operations role—you’ll host engaging tastings, support wine club growth, help manage inventory flow, and assist with order fulfillment along the way. It’s a great fit for someone who’s detail-oriented, proactive, and excited to grow within winery direct-to-consumer operations.

We’re a collaborative team with a casual, thoughtful, quality-driven vibe, and we’re looking for someone who’s curious, dependable, and enjoys taking ownership of their work while learning as they go.

What You’ll Do:
Hospitality & Guest Experience (˜50%)
- Host welcoming, relaxed, and educational tasting experiences
- Share our wines, story, and wine club with confidence and authenticity
- Support tasting room sales and wine club signups
- Assist with events and elevated guest experiences
- Maintain a polished but approachable tasting room environment

Operations & Fulfillment (˜50%)
- Assist with tasting room inventory tracking and restocking
- Pick, pack, and prepare outbound wine shipments
- Coordinate will-call and customer pickup orders
- Maintain organized storage and shipping areas
- Monitor supply levels (wine, packaging materials, merchandise)
- Support coordination between tasting room and operations workflows

We’re Looking For Someone Who:
- Enjoys both guest-facing work and structured operational responsibilities
- Is detail-oriented and dependable
- Takes initiative and follows through
- Works well independently and collaboratively
- Is comfortable shifting between hospitality and fulfillment tasks throughout the day
- Is available weekends
- Can lift and move up to 40 lbs
- Winery, tasting room, or hospitality experience
- Inventory, logistics, or fulfillment experience
- POS or wine club platform familiarity
- Interest in growing into DTC, wine club, or operations leadership roles

Growth Opportunities:
This role is designed as a development pathway for someone interested in building a long-term career in winery hospitality and direct-to-consumer operations. Strong performers will have opportunities to take on increasing responsibility across guest experience, wine club support, inventory coordination, fulfillment workflows, and event execution, with potential for expanded leadership within tasting room and operational functions over time.

A little about working at Winderlea:
Winderlea is a family-owned, certified Biodynamic® and B Corp winery on historic Worden Hill Road in the Dundee Hills of Oregon. For nearly two decades, we’ve built one of Oregon’s most respected boutique wine brands, producing 5,000 cases of premium Pinot noir, Chardonnay, sparkling wine, and more from our two estate vineyards. Today, under new family ownership and leadership from the Ricci family, we’re investing in the future and building the team and culture that will shape Winderlea’s next chapter. As a small, hands-on team, we value creativity, collaboration, and a fun, energetic workplace where ideas are welcomed and everyone contributes. This is a rare chance to join a respected Oregon winery at an exciting moment of growth and possibility.

Compensation & Benefits:
- Hourly rate ($25-$28) with tips
- Full-time position
- Hands-on exposure to both hospitality and winery operations
- Ongoing wine education opportunities
- Employee wine discounts (if applicable)
- Supportive, team-oriented environment with room to grow
- Employee health benefits

Equal Opportunity Employer:
We are an equal opportunity employer and welcome applicants from all backgrounds and experiences. We are committed to creating an inclusive workplace where everyone feels valued and supported.