Are you a natural salesperson who loves wine, connecting with people, and turning great conversations into great sales? We’re looking for a Direct-to-Consumer (DTC) Wine Sales Specialist to join our Wine Club team and help grow our business through meaningful, relationship-driven sales. This is an opportunity for someone who is energized by sales goals, confident picking up the phone, and passionate about helping customers discover wines and experiences they’ll love. In this role, you’ll connect with wine club members, loyal customers, prospective guests, and new customers through personalized inbound and outbound sales conversations. You’ll introduce customers to new releases, limited allocations, events, wine club memberships, and other offerings while building relationships that encourage long-term loyalty.

If you’re competitive in the best way, love the thrill of closing a sale, and believe that selling wine should feel personal—not transactional—we’d love to meet you.



Why Work With Us?

- Flexibility to work a hybrid remote schedule.
- Enjoy 10 paid holidays and accrue up to 3 weeks of vacation annually.
- Benefit from up to 8+ sick days per year.
- Receive comprehensive Medical, Dental, and Vision Insurance (80% covered by Testarossa).
- Participate in our 401(k) Retirement Savings Plan with employer match.
- Take advantage of Flexible Spending Accounts for both Medical & Dependent Care.
- Receive a 50% discount on all wines and additional winery perks.
- Gain peace of mind with Long Term Disability, Life Insurance, and Employee Assistance Program (EAP).
- Refer new employees and benefit from our Employee Referral Program.
- Work in a beautiful, historic environment alongside passionate and fun colleagues.

What You’ll Do

Direct-to-Consumer Phone Sales

- Conduct outbound sales calls to wine club members, loyal customers, and prospective guests to promote wine releases, allocation offerings, special events, seasonal promotions, and other revenue-generating opportunities.
- Build and maintain strong customer relationships through personalized, consultative sales conversations designed to increase conversion, purchase frequency, and customer lifetime value.
- Achieve individual sales goals while contributing to overall DTC revenue objectives.
- Follow up on abandoned carts, reservation inquiries, event attendees, wine club prospects, and other qualified leads to maximize conversion opportunities.
- Maintain accurate customer records, sales activity, and communication notes in CRM and POS systems, including daily tracking of outbound activity, to support effective follow-up and sales conversion.
- Recommend wines, wine club memberships, experiences, and promotional offers based on customer preferences and purchase history, with a focus on increasing average order value and overall customer spend.
- Process orders accurately and efficiently according to winery procedures.

Direct-to-Consumer Inbound Sales

- Respond promptly and proactively to inbound sales inquiries via phone, email, and text, converting inquiries into wine, wine club, event, and merchandise sales.
- Process customer orders generated through inbound sales campaigns and other DTC marketing initiatives.
- Provide knowledgeable product recommendations, identify upselling and cross-selling opportunities, and guide customers toward purchases that align with their interests and the winery’s sales objectives.

Wine Club & Business Support

- Provide occasional support to the Wine Club team with member communications, account updates, shipment processing, and retention initiatives as needed.
- Support winery events, special promotions, and seasonal campaigns that create opportunities for DTC sales and customer engagement.
- Maintain knowledge of the winery’s wines, experiences, events, and wine club offerings to effectively support sales conversations.
- Perform additional duties as assigned.

You’ll be a great fit if you have:

- Proven sales experience with a demonstrated ability to meet or exceed performance goals.
- At least one year of experience in customer service, hospitality, retail sales, call center, or the wine industry.
- A natural ability to build rapport, ask great questions, listen to customers, and create personalized recommendations.
- Excellent verbal and written communication skills.
- Strong organizational skills and excellent attention to detail.
- The ability to prioritize, multitask, and thrive in a fast-paced environment.
- Proficiency with Microsoft Office Suite and customer relationship management systems.
- Passion for wine, hospitality, and relationship-building, with the ability to provide personalized service that drives wine sales, wine club retention, and memorable customer experiences.
- Knowledge of wine, wine regions, and wine pairings.
- Experience with CRM software and POS systems; Commerce7 experience is preferred.
- A degree in Sales, Marketing, Business, or a related field is preferred, but we value relevant sales and hospitality experience just as highly.


Work Environment & Physical Demands

- Full-time, non-exempt position reporting to the Wine Club Manager.
- Must be available to work occasional weekends, holidays, and evenings.
- Ability to remain seated for extended periods and regularly climb stairs.
- Ability to work at a computer and on the telephone for prolonged periods of time.
- Ability to occasionally lift and carry up to 40 pounds.