Job Description

What we’ll call you:

Head of Inside Wine Sales

Our purpose?

Glad you asked. In a nutshell, we’re all about making the world of wine a better place. We fund and source directly from independent winemakers to bring customers better quality wine for a better price. No thirsty middlemen as far as the eye can see.

It’s a different way of doing things, sure. But it works. We’re currently the largest online direct-to-consumer winery in the USA, shipping over 1 million(!) packs a year to curious wine lovers. And with an ambitious road ahead, we’ve got no plans on plugging the cork on growth.

Our global team (we have offices in the UK and Australia, too) is entrepreneurial by nature, obsessive about customer experience and driven by performance. All things that make Naked a great place to grow both personally and professionally. And yes, we like wine. A lot.

Your purpose:

At Naked Wines, our Wine Advisors are at the heart of what makes us special. They act as our customers' very own personal sommeliers, guiding them to wines they’ll love, deepening their knowledge, and enhancing their Naked experience. They are not just salespeople; they are relationship builders, educators, and storytellers. As the Head of Wine Advisors, you would be the driving force behind who will lead and inspire our 35+ strong outbound UK and US-based Wine Advisor team, ensuring they deliver exceptional customer experiences while driving retention, loyalty, and sales.

This role requires a leader who can deeply understand and champion the Wine Advisor function, ensuring they remain a critical, high-value part of the Naked Wines experience. You’ll be responsible for team leadership, performance management, target setting, and an evolving compensation structures to align with broader customer engagement goals. This role will also support the Wine Advisors’ engagement in customer facing marketing strategies, like developing content for Naked’s social media channels, email campaigns, etc. 
If you thrive on leading, collaboration, and have a passion for the perfect pour, this role is for you!

To nail this job, you will be responsible for:

Team Leadership & Development:

• Lead, mentor, and develop a team of 35+ Wine Advisors, ensuring they are empowered to deliver outstanding customer experiences.
• Manage and coach direct team leads, ensuring they provide strong leadership and support to their teams.
• Foster a positive, high-performance culture, where advisors feel valued, motivated, and aligned to both customer and business goals.

Strategy & Performance Management:

• Establish long-term vision and strategy for the WAT team, using data and competitor analysis to inform a test-and-learn agenda
• Define and consolidate clear targets, KPIs, and commission structures, moving beyond pure sales to include customer loyalty, attrition reduction, and advocacy.
• Develop strategies to optimize call quality, conversion rates, and overall customer engagement.
• Partner with analytics team to build understanding of incrementality of WAT-generated activity and longer-term retention impact
• Leverage data and insights to continuously refine advisor strategies, ensuring the team meets and exceeds performance goals.

Customer Experience & Retention:

• Ensure Wine Advisors focus on long-term customer relationships, not just short-term sales, driving retention and advocacy.
• Champion proactive customer engagement, ensuring advisors provide relevant recommendations, personal touches, and memorable interactions.
• Partner with CRM, Loyalty, and Data teams to identify high-value customer segments and tailor advisor outreach accordingly.

Brand Advocacy & Social Engagement:

• Partner with the brand team to position Wine Advisors as a key face of Naked Wines across social media, showcasing expertise, personality, and authenticity.
• Develop and support content initiatives featuring Wine Advisors, ensuring they engage, educate, and entertain customers.
• Ensure social activity complements outbound efforts, strengthening Naked’s direct relationships with customers.

Operational Excellence & Innovation:

• Continuously improve team processes, training, and tools to enhance effectiveness and efficiency.
• Introduce new ways to measure, recognize, and reward advisor success, ensuring alignment with business objectives.
• Keep up with industry trends, ensuring Naked Wines sets the standard for premium wine advisory services.

We’ll love you because you have:

• A deep understanding of wine and a passion for customer education and engagement.
• Proven leadership experience managing outbound sales, customer experience, or advisory teams.
• Experience developing performance targets, incentive structures, and compensation models.
• A strategic, data-driven approach to team performance, engagement, and customer retention.
• Strong ability to coach, develop, and inspire large teams, creating a culture of motivation and success.
• A social-first mindset, with an understanding of how advisors can elevate the brand online.
• A love of wine (or a strong curiosity to learn!).

Finally, you live by our Naked values:

• We are Naked Together: Supporting all stakeholders from the winemaker to the customer.
• We embrace growth: Pushing ourselves out of our comfort zones to overcome obstacles.
• We always start with our customers and winemakers.
• We keep it simple and are data-led.
• We do the right thing, holding ourselves accountable with honesty and openness.

This is an incredible opportunity to lead one of the most distinctive and impactful teams at Naked Wines, ensuring our Wine Advisors remain the gold standard in personalized wine recommendations, customer engagement, and brand storytelling. If you’re a strategic, customer-obsessed leader with a passion for building relationships, driving performance, and elevating brand engagement, we’d love to hear from you!

Requirements

• Work a hybrid schedule (mix of in office and at home work)

• Ability to work a flexible schedule to accommodate various timezones

• Bachelor’s degree in related field preferred

• At least 4 years of wine or other beverage industry experience required

• Sales experience required

• Experience leading and managing large teams

• Strong computer, technical and analytical skills required

• An equivalent combination of education and experience is acceptable

• Comprehensive knowledge of Microsoft Office tools and Google Office tools

• Skilled with MS office Suite (Word, Excel, PPT) and/or Google Sheets

• Must be at least 21 years of age.

Benefits

Compensation and benefits:

• Compensation: Sonoma, CA- $137,000; Denver, CO- $129,000 Annually DOE
• Annual Bonus
• Health, Dental, and Vision Insurance – 90% employee coverage, 60% dependent coverage. Eligible from day 1.
• Holiday allowance – 34 days of paid time off, including 20 days of accrued paid time off (PTO) and 12 paid company holidays. Paid time off also includes your Birthday, plus one additional day for volunteer efforts.
• Retirement plan – 4% employer match. Eligible from day 1.
• Wine allowance – $50 a month towards your Nakedwines.com account
• Gym contribution – Up to $25 a month towards a gym membership
• Personal Pathways – Naked will pay up to $500 annually towards training on any topic you may be interested in pursuing (doesn't have to be work-related)
• Company Share Plan

If you think you fit the bill, we want to hear from you. Get the ball rolling and hit ‘Apply’ now.

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