Head of Retail & Sommelier (Cayman Islands)

Head of Retail & Sommelier (Cayman Islands)

I’ll Drink to That! Fine Wine & Spirits Emporium

George Town, Grand Cayman Cayman Islands

Company : I’ll Drink to That! Fine Wine & Spirits Emporium Ltd.

Location : Seven Mile Beach, Grand Cayman (on-site)

Reports to : Founder & Managing Director

Start : ASAP (ahead of store opening in ~6 weeks)

About IDTT

I’ll Drink to That! (IDTT) blends old-world hospitality with modern retail innovation—curated wine & spirits, an AI wine recommendation kiosk, smart-locker pickup, reliable delivery, and a tiered membership with NFC / Wallet passes. We’re a bold, exciting brand intent on birthing a trendy culture of wine and spirits retailing where every visit feels like a welcomed adventure and discovery. We’ve worked hard to make each trip a visual treat—tactile materials, clean modern displays, and thoughtful storytelling. Our tagline says it all : “Let’s toast to the Soul!”

Role summary

Be the face of our wine program and co-pilot the flagship store alongside the Retail Operations Manager. You’ll lead the team on the floor, elevate guest experience, curate the range, host tastings, and turn guided recommendations (AI + human) into bigger baskets and repeat visits. You’ll also support product procurement, trend awareness, and brand selection that keep IDTT fresh and exciting.

What you’ll do

• Operations & People (guest-facing leadership)

Lead daily floor ops : opening / closing walkthroughs, service standards, cash-handling oversight.

Act as in-house sommelier during peaks; guide pairings and responsibly trade up.

Curate seasonal and demand-driven assortment; maintain planograms and presentation standards.

Keep Shopify POS / eComm guest-facing details sharp (descriptions, tags, photos, food-pairing notes).

Enforce strict ID verification at checkout, tastings, deliveries, and locker pickups.

What success looks like

What you bring

Ramp timeline

Compensation & benefits

The Cayman Islands is tax-free, enjoys a high standard of living, and offers a premium environment for a career-defining role at launch. The store is projected to generate over USD $2M in annual revenue.

A final note

This is a serious, career-defining role for a highly qualified professional who wants to help build Cayman’s most innovative retail concept. Our flagship store is opening in the next 6 weeks, so please apply quickly if you’re ready to make your mark.

How to apply

Send your CV, a brief note on a successful tasting / event you led (what you did, results), and your top three favorite food-pairing “crowd-pleasers”.

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Contact Information

I’ll Drink to That! Fine Wine & Spirits Emporium

Damien Dilbert

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