Schooner caribbean.work
Why Schooner Interface How it works FAQ
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Starting in Cayman

Your personal agent for job search.

Schooner reads every open vacancy in Cayman, scores each one against your background, and drafts the application when you say yes.

Private pilot, free while it runs. You'll get an invite as spots open. Privacy

2,500+ Live postings tracked
65+ Sources read

Every source is read twice a day, morning and evening.

S
Schooneronline
NEW MATCH · 84/100 STRONG APPLY Senior Fund Administrator — Suntera KYD 75–95K · Senior level You meet three of the four stated requirements. The gap is supervisory experience. 2 people have applied so far. Want me to draft your application? 16:31
Yes, draft it 16:33 ✓✓

Every vacancy on the island, wherever it's posted.

Cayman first. The same rail is built to expand across the Caribbean, island by island.

Why Schooner

The listings already exist. Finding yours is the work.

The whole market, one place

The portal where every work-permit vacancy must be advertised, plus recruiters, employer career pages, and classifieds. Schooner reads all of them twice a day, so what you see does not depend on who you know.

Scored against your background

Each posting comes back with a number and the reason for it — what you match, what you are missing, and whether it is worth your time.

Just a chat thread

Schooner is a chat thread: Telegram during the pilot, WhatsApp to follow. No account to create and no portal to check. Send your CV if you have one, or just tell it about your work.

The interface

It lives where you already are.

→No portal, no new habit — Telegram during the pilot, then WhatsApp, the region's default channel
→Voice notes welcome — answer out loud when that's easier
→Honest digests — real gaps, real applicant counts
→Nothing sent without a human yes — every submission approved in‑chat
S
Schooneronline
Welcome to Schooner — I'll watch every job in Cayman for you. Tell me about your work. A voice note is perfect. 9:02
▶ 0:42
9:04 ✓✓
Got it — fund accountant, 6 years, ACCA part-qualified, Caymanian. Profile saved ✓ Watching 2,500+ live postings for you. 9:05
New match · 84 STRONG APPLY
Senior Fund Administrator — Suntera
Honest gap: wants supervisory experience.
Only 2 people have applied.
Want me to draft your application? 16:31
Yes — apply 16:33 ✓✓
PDFCV + cover letterdrafted for this role
Review before anything is sent. 16:35
How it works

Three messages from start to applied.

Join the waitlist →
01 Send one message

Message Schooner on Telegram during the pilot. It asks about your work, your skills and what you want next, then shows you the profile it built to confirm. Send your CV and it starts from that.

02 Get scored matches

Twice a day Schooner pulls every new posting, scores each one against your profile, and sends only the ones worth reading.

03 Apply in one reply

Reply to a match and Schooner drafts the application against that posting. You read it, change what you want, and send.

FAQ

Questions people ask first.

Yes — during the private pilot, Schooner is completely free. At launch there will be free and paid tiers, and you choose whichever fits you.

The name

Named for the boats that carried Caymanians to work.

Turtling schooners built in the Cayman Brac yards took Caymanian crews to Cuba and Central America to earn a living. Schooner does the same job from a phone.

Watercolour of a Cayman Brac turtling schooner under sail, two catboats lashed on deck
Private pilot

Get on the list for an invite.

Free during the pilot. Used only to invite you. Privacy