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.

Hire, train, schedule, and coach with the ROM (via Easyteam); build a positive, high-accountability culture.

Run 10-minute morning huddles; translate KPIs into clear actions for the team.

Customer Experience & Education

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

Host twice-monthly tasting events (Fri 6–7:30 pm) with crisp education modules; coordinate light bites with XQ’s Restaurant.

Champion membership sign-ups, NFC/Wallet usage, and referral flows at checkout.

Merchandising, Assortment & Procurement

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

Review Prediko reorder drafts with the ROM; manage case-size realities to ensure in-stock levels without overbuying.

Source consumer-friendly, trend-driven brands; assist owner in selecting innovative and attractive labels.

Accompany the Founder to international trade shows for product procurement and trend scouting.

Omnichannel & Tech (coordination with ROM)

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

Ensure receiving/UPC accuracy is enforced on the floor; flag issues to ROM.

Oversee smart-locker readiness on the floor (= 2 hours) and coordinate with ROM on delivery routing.

Compliance & Safety

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

Maintain liquor license conditions, cash/security protocols, and PCI-compliant practices.

What success looks like

In-stock = 98%; out-of-stock = 2%.

AOV and attach-rate up following tastings/promos.

Membership penetration and referrals trending up.

Locker ready = 2h; delivery on-time = 95%.

Accurate, guest-facing product content with no reconciliation surprises.

What you bring

5+ years in wine/spirits retail, restaurant beverage leadership, or premium grocery; store/department leadership experience.

WSET Level 3 (or equivalent) required; Diploma a plus. Confident presenter and educator.

Strong merchandising eye; event-hosting energy; guest-first mindset.

Informed about global wine & spirits trends and able to translate them into consumer-friendly, attractive brand selections.

Comfortable with Shopify POS/eCommerce, Google Sheets/Airtable; quick study on Prediko/Easyteam.

Valid driver’s license; able to travel for supplier pickups and trade shows.

Willingness to travel intermittently to Cayman Brac to support the second store.

Legally authorized to work in Cayman (work permit sponsorship possible).

30/60/90 ramp

30 days: Learn systems; finalize opening list/planogram; train team on service, ID checks, and membership flow; run first tasting.

60 days: Hit in-stock targets (with ROM); tastings driving measurable lift; SOPs locked for receiving/UPCs/locker.

90 days: KPIs steady; event calendar humming; procurement and trend feedback cycle established with Founder.

Compensation & benefits

Full-time, on-site; evenings/weekends for tastings and retail peaks.

Base salary paid in Cayman Islands Dollars (KYD): KYD $4,000/month (equivalent to USD $5,000).

For the right candidate (“unicorn” blend of operations + sommelier):

Quarterly profit-share bonus (up to 10%).

Equity participation pathway (terms apply).

All roles receive an additional KYD $1,000/month (equivalent to USD $1,250) upon the opening of our second store (Cayman Brac, targeted Jan 2026).

50% health insurance contribution + standard pension contributions.

The Cayman Islands is tax-free, enjoys the highest standard of living in the Caribbean, and is known as one of the most beautiful, safe, and clean environments in the region. With its elevated clientele and vibrant economy, this is a unique opportunity to join a premium brand at launch.

The store is projected to generate over USD $2M in annual revenue, offering significant growth potential for the right candidate.

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”.