Schooner caribbean.work
The idea The insight Working today Workflow The big idea
Why me · why now
Future Caribbean · Open Track

Schooner.

One profile, every island.

The Caribbean labour rail — agentic infrastructure that moves the region's workers into the region's jobs.

S
Senior Fund Administrator Suntera · Cayman Islands
KYD 75–95K On-island Senior level
Schooner's read
6 years fund accounting Caymanian status is a hiring advantage here No supervisory experience
84/100 · Strong apply
Only 2 people have applied
Daniel Cimring · repeat founder · Cayman Islands caribbean.work
The initial idea

Your own agent, living in WhatsApp, whose only job is getting you a job.

It started with an open source project that caught fire: an agentic framework that reads job postings, scores them against your background, tailors your CV and drafts the cover letter. Tens of thousands of people starred it in weeks. Its author used it to send 69 applications and land an offer.

The whole application loop is agentic — evaluate, tailor, draft, prep, track
The demand is not theoretical — tens of thousands of stars, thousands of forks, in weeks
But it lives on a laptop — Python, LaTeX, a terminal and a subscription
Open source · the proof MadsLorentzen/ai-job-search
★ 25k+ stars⑂ 8k+ forks

The job search that runs on your machine — evaluate postings, tailor CVs, write cover letters, prep interviews.

69 applications · 1 offer its author, on himself

The surface

From a terminal command to a WhatsApp thread — no install, voice notes instead of config files.

The posture

From you remembering to run it to it running for you — always on, watching the market while you work.

The data

From whatever job boards you can scrape to every vacancy on the island, guaranteed.

The first two were product decisions. The third one turned out to be the whole company.

The insight

On many islands, every job vacancy is posted by law. Nobody has built on it.

1,607 live postings — the entire formal Cayman market
2×/day full-market pull, every day since July
100% coverage guaranteed by the work-permit process
2 islands confirmed: Cayman proven, Bermuda next

Salaries, deadlines, even live applicant counts — a whole-market dataset LinkedIn will never integrate, compounding daily.

Working today — not a mock-up
WhatsApp interview voice-note-first Two-stage matcher immigration-aware Honest digest human-approved
Match digest — live output
84 · STRONG APPLY — Senior Fund Administrator, Suntera (Cayman)
Caymanian status is a hiring advantage here.
Honest gap: role wants supervisory experience — you have none yet.
Only 2 people have applied to this job.

Ran end-to-end this week on all 1,607 postings — ~$0.60 to match one candidate against the whole market. A free deterministic filter narrows to ~20, the LLM scores those at 3¢ each. Nothing is ever submitted without a human yes.

S
Schooneronline
Welcome to Schooner — one profile, every island. Tell me about your work. A voice note is perfect. 9:02
0:42
9:04 ✓✓
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
The agentic workflow

Data sources

WORC JobsCayman gov portal JSON API Bermuda Job Board sprint · island #2 Recruiter boards Baraud · Affinity

Ingestion & watchdog

Ingestion agents poll 2–4×/day Market DB postings · salaries · applicant counts Watchdog agent ghost postings · permit reposts

Outputs & intelligence

Priority alerts to qualified locals Gov dashboards salaries · skills gaps Employer reverse-match sprint
01WhatsApp onboardingvoice-note interview
02Human gateprofile confirmed
03Stage 1 prefilterdeterministic · recall-first
04Stage 2 LLM scorer6 dims · immigration fit · honest gaps
05Match digestlive applicant counts
06Human gateuser picks: apply / skip
07Drafter → ReviewerCV + cover letter PDFs
08Human gatedocs approved
09Dispatchemail auto-send 13% · portal handoff 86%
10Outcome trackerreplies · interviews · hires
↑ Market DB feeds the rail — every posting, twice daily ↩ Outcomes recalibrate the scorer · nothing submitted without a human yes
The big idea

The Caribbean loses its people and imports its workers.

Brain drain and labour shortage at once — because a worker on one island can't see the job one island over. A coordination failure, and those are solvable.

Locals considered first — agents that catch ghost postings
A portable skills passport — CARICOM free movement, made real
Live labour intelligence — for governments steering on 2 surveys/year
Cayman · live Bermuda · island #2 Jamaica Barbados Trinidad Bahamas 44 million people · ~30 markets · one rail
Why me · why now

The dataset compounds every day. I'm the only one collecting it.

Built & ran a profitable mobile social network for 10 years — the long version of a company
On-island, technical, full-time — 8 months of intensive agentic building
Whole-market coverage is a legal guarantee, not a promise — and it's already flowing
The 21-day sprint: WhatsApp loop live with pilot users · island #2 (Bermuda) on the rail · the local-first accountability layer shipped.