Company: I’ll Drink to That! Fine Wine & Spirits Emporium Ltd.
Location: Seven Mile Beach, Grand Cayman (Caribbean)
Reports to: Founder & Managing Director
Start: On or before December 2025
Salary: KYD $60,000/year + benefits + attainable profit bonus + equity pathway
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About IDTT
I’ll Drink to That! (IDTT) is a bold and exciting new retail brand in the Cayman Islands — blending old-world hospitality with cutting-edge retail features. Our flagship location on Seven Mile Beach will feature curated selections, an AI-powered wine recommendation kiosk, smart-locker pickup, seamless delivery, and a tiered membership program with NFC/Wallet passes.
Our vision is to create Cayman’s premier fine wine & spirits destination, one that transforms shopping into a welcoming adventure and cultural experience. Every visit is designed as a visual treat, blending cellar-inspired design with modern service. Our tagline says it best: “Let’s toast to the Soul!”
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Why Grand Cayman?
• Tax-free jurisdiction: Salaries are received net, with no income tax.
• High standard of living: The Cayman Islands consistently ranks as the safest, cleanest, and most prosperous destination in the Caribbean.
• Lifestyle: Miles of pristine beaches, world-class diving, international schools, and a cosmopolitan community.
• Opportunity: Be part of a groundbreaking retail concept at launch — with a direct line to ownership and a clear growth pathway.
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Role summary
The Head of Retail & Sommelier will own the daily operations of the flagship store while being a customer-facing, hands-on leader. You’ll be on the floor assisting guests, guiding pairings, hosting tastings, and setting the standard for service.
Beyond daily retail, you’ll play a strategic leadership role: helping shape purchasing and importation channels for wine & spirits, advising on brand selection, and traveling abroad to trade shows, distributors, and producers.
This is a career-defining international posting for an ambitious wine professional who wants to combine sommelier-level expertise with retail leadership in one of the most dynamic markets in the Caribbean.
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What you’ll do
Operations & People
• Lead daily operations: floor service, cash controls, opening/closing.
• Hire, train, and coach staff to uphold international service standards.
• Run daily huddles and track/store KPIs.
Customer Experience & Education
• Be highly visible on the floor, guiding wine & spirits pairings.
• Act as the in-house sommelier during peak hours.
• Host twice-monthly tastings (Fri 6–7:30pm), with engaging education modules.
• Champion memberships, referrals, and NFC/Wallet adoption at checkout.
Merchandising, Buying & Stock
• Curate seasonal assortments that balance global and regional preferences.
• Approve predictive reorder drafts in Prediko, balancing stock levels against case-size constraints.
• Develop bundles and pairings (e.g., glassware, food matches) to increase sales.
• Advise and assist the owner in creating and managing import channels for wine & spirits into the Cayman Islands.
Trade & Supplier Relations
• Travel internationally to trade shows and wineries/distilleries to secure unique products.
• Build lasting distributor and producer relationships.
Omnichannel & Tech
• Maintain Shopify POS/eCommerce alignment (pricing, UPCs, photos, tags).
• Oversee smart-locker order fulfillment (≤2 hours) and delivery routing.
Compliance & Safety
• Enforce ID verification for every sale/delivery.
• Uphold Cayman liquor license regulations, security, and compliance.
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Work schedule overview
• The store operates 10:00am – 8:00pm Monday through Saturday, and 1:00pm – 7:00pm on Sunday.
• Full-time schedule: 45 hours per week, spread across 5 or 6 days depending on business needs.
• Regular evenings and weekends are required, especially for tastings and seasonal peaks.
• Work on public holidays may be required; staff working holidays receive double time wages.
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What you bring
• 5+ years in premium wine/spirits retail, restaurant beverage leadership, or specialty grocery.
• WSET Level 3 (or equivalent) required; Diploma strongly preferred.
• Strong buying and merchandising experience.
• Hands-on leadership style; thrives in customer-facing environments.
• Willingness and ability to travel internationally for trade shows and supplier visits.
• Strong knowledge of global wine/spirits trends and ability to translate them for consumers.
• Tech-competent: Shopify POS, Google Sheets, Airtable (Prediko/Easyteam a plus).
• Valid driver’s license preferred.
• Must be willing to relocate to the Cayman Islands; work permit sponsorship is available for qualified candidates.
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Compensation & benefits
• KYD $60,000/year base salary (~USD $75,000 equivalent).
• Cayman Islands is a tax-free country — your take-home pay is maximized.
• 10% profit bonus structure is realistically attainable, with total compensation exceeding USD $100,000/year possible.
• Equity pathway: After 3 years of proven performance, candidates may be invited into equity participation with little to no capital investment required.
• 50% health insurance contribution + standard pension contributions.
• Paid international travel to trade shows and producer meetings.
• Ongoing training, tastings, and professional development support.
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A final note
This is a rare opportunity to take a leadership role at launch in one of the Caribbean’s most dynamic retail projects. You’ll be both a hands-on sommelier and a strategic advisor, helping shape Cayman’s wine & spirits culture from the ground up.
The store opens November 10, 2025, and the successful candidate must be ready to start on or before December 2025.
Qualified international applicants are encouraged to apply. Work permit sponsorship is available.