Built in Jamaica for founder-led companies
A nearshore sales team that books and closes your B2B deals
We find, book and close high-ticket B2B deals for founder-led companies, during your business hours.
For offers that sell for $1,000 or more per sale
For founders who still do all the selling
What if selling didn’t stop every time you got busy?
We find the prospects, book the calls and close the deals, so you can get back to running the company.
- Right now
Right now you’re probably doing all of it:
- Writing the outreach
- Chasing replies
- Taking every call
- Sending proposals at night once the client work is done
And it works, right up until you get busy. Then the selling stops, and a couple of months later you feel it in the revenue.
- With us
That’s the part we take off your hands. Our team learns your offer, your ideal client and your market before anyone picks up the phone for you. Then we take over the selling, one stage or all of it, and you can see every call and every deal in your own CRM.
You stay in control. You just stop carrying it all by yourself.
From prospect list to signed deal
Four ways we can sell for you
Lead Generation finds prospects, Appointment Setting books them, Sales Closers closes the leads you already have, and Full-Cycle Sales runs the whole process.
For teams that want more pipeline
Lead Generation
We find prospects who fit your ideal customer, reach out by cold email and LinkedIn, and send you a steady flow of qualified replies, so all you have to do is run the meetings.
For founders too busy to prospect
Appointment Setting
We put qualified meetings on your calendar from our cold email and LinkedIn outreach, booked by the prospects themselves or by a dedicated Sales Development Representative (SDR) on our team, so you just show up and sell.
For founders ready to hand off sales
Full-Cycle Sales
We run the whole thing for you, from outreach and booking to a closer who takes the call and follows up to the close, so your proven offer keeps selling without you on every call.
For dedicated deal follow-up
Sales Closers
Our commission-based closers take the leads you already have but can’t get to, run the calls and keep following up until each deal closes.
For more detail, see all our sales services.
Who we sell for
Built for founder-led B2B companies in six sectors
We work with businesses whose offers sell for $1,000 or more per sale. These are the sectors we focus on first, and the sales problem each one runs into.
B2B SaaS
Demo requests and trial sign-ups come in, but nobody calls them the same day. By the time someone does, the prospect has moved on.
Marketing, advertising and media agencies
New business runs on referrals, so the pipeline swings between feast and famine, and the founder still pitches every new account.
Coaches and consultants
You’re the product and the salesperson. Discovery calls get squeezed between client sessions, and follow-up is the first thing to slip.
Financial services, including commercial insurance brokers and MGAs
Your best producers spend their days servicing the book you already have, so new business waits. Brokers need new accounts, and MGAs need more retail agencies sending submissions, but nobody has time to go and find them.
We support financial services firms with Lead Generation and Appointment Setting.
Directories and platforms
You sell listings, memberships or advertising to many small businesses. That’s more conversations than one founder can hold.
Commercial solar, energy efficiency and home improvement
Quote requests and site visits come in, then stall. The prospect is interested, but nobody follows up after the first visit.
Don’t see your sector? If your offer sells for $1,000 or more and you’re still the main closer, book a strategy call. We’ll tell you straight whether we can help, because we turn down clients we can’t.
Start where things stall
How to choose the right sales service for your business
Find where your sales process stalls, then match it to a service.
You need new prospects, and your team can run its own meetings.
You’re good on sales calls but don’t have time to find and book them.
You’re still running every sales call and want the whole process off your plate.
You have more leads than you can close, and leads go cold.
You don’t have a defined ideal customer, sales assets or a playbook yet. Start with our Sales Enablement add-on alongside any service.
Not sure which fits? Book a 30-minute strategy call and we’ll recommend one based on your offer and lead flow.
Headquartered in Westmoreland, Jamaica
Your nearshore sales team, based in the Caribbean
Caribbean outsourcing with us covers sales only: finding prospects, booking meetings and closing B2B deals. If you’re weighing Jamaica sales outsourcing, here are the basics. We’re headquartered in Westmoreland, Jamaica. Our reps sell in English. Our reps work during your business hours.
For buyers in the US and Canada:
Nearshore means your sales team works from a nearby region in similar time zones. Ours is based across the Caribbean and Latin America. Our reps work across the Caribbean and Latin America, within three hours of US Eastern time. Jamaica stays on Eastern Standard Time (UTC-5) all year and does not change its clocks.
You don’t find, pay or manage the reps yourself. We handle selection, training and management. Our reps are trained, managed and quality-checked by our team. A manager reviews recorded calls and gives each rep feedback.
Five stages, every service
How an engagement runs, step by step
Every engagement follows the same five steps.
Strategy call
A 30-minute Zoom call with one of our sales strategists about your offer, your lead flow and which service fits.
Onboarding
You share your ideal customer profile, offer details, case studies and sales assets, plus calendar and CRM access.
CRM check
Your reps log every call, email and meeting in an approved CRM, such as HubSpot, Close, HighLevel or Salesforce. If you need one set up, implementation is billed separately.
Go-live
Onboarding usually takes about 14 days for small teams, and 30 to 45 days for larger teams or clients without their own CRM or systems.
Weekly reports and monthly reviews
A written report every week, and a review call each month to adjust targeting and messaging.
A one-time setup fee starting at $850 and a flat monthly agency fee. See how our pricing works.
Consultative, high-ticket B2B selling
What makes us different
Every sales rep is trained on your offer before going live.
We work with businesses in the United States, Canada, the United Kingdom, Europe and the Caribbean.
Unlike a call center, we:
- Sell high-ticket offers, not high-volume scripts
- Hire reps who know how to sell consultatively
- Keep training and coaching reps long after they go live
- Put reps live only once they know your ideal client, offer and market
Launched June 13, 2025
Our progress so far, and how you track our work
22
sales reps placed
4
clients
Caribbean Closers launched on June 13, 2025. We signed our first client in October 2025, our second in February 2026, and our third and fourth in September 2026. We have now placed 22 sales reps across four clients, and our current suite of sales services launched in November 2026.
June 2025
Caribbean Closers launches
October 2025
First client signed
February 2026
Second client signed
September 2026
Third and fourth clients signed
November 2026
Current suite of sales services launches
How you track our work
CRM visibility
Every call, email and meeting is logged in your CRM, so you can check activity and pipeline at any time.
Weekly written report
You get a written report every week.
Monthly review call
And a review call once a month.
Results depend on your offer and lead quality, so we don’t guarantee meetings, revenue or close rates.
B2B marketplaces
Find us on GoodFirms and DesignRush
Before you book
Questions founders ask about Caribbean Closers
What is Caribbean Closers?
Caribbean Closers is an outsourced sales company, headquartered in Jamaica, that finds, books and closes high-ticket B2B deals for founder-led companies. It offers four sales services: Lead Generation, Appointment Setting, Full-Cycle Sales and Sales Closers. It is a division of Pineapple Connect LLC, founded by Mellesia Lewis.
Where is Caribbean Closers based?
Caribbean Closers is headquartered in Westmoreland, Jamaica. Our sales reps are based across the Caribbean and Latin America. We work with businesses in the United States, Canada, the United Kingdom, Europe and the Caribbean. It was founded in 2025.
Which sales service should I start with?
Start where your sales process stalls. Need prospects? Try Lead Generation services. Need meetings booked? Try our Appointment Setting service. Leads going cold? Try commission-based Sales Closers. Want it all handled? Try Full-Cycle Sales from outreach to close. We confirm the fit on your strategy call.
How much does Caribbean Closers cost to start?
A one-time setup fee starting at $850, a flat monthly agency fee for teams of 1–3 sales reps, and commission for closers on closed deals. Sales Development Representatives (SDRs) are paid per appointment. Minimum term: 12 months for engagements with an SDR or closer, 3 months for outreach-only engagements. View full pricing details.
Who is Caribbean Closers a good fit for?
We work with businesses whose offers sell for $1,000 or more per sale. Our clients are founder-led B2B businesses with a proven offer, where the founder is still the main closer. The buyer is the founder, CEO or head of sales. Not the right fit if your offer sells for under $1,000, or you are looking for a month-to-month arrangement.
Your next step
Start with a 30-minute Caribbean Closers strategy call
Your next step is a 30-minute Zoom call with one of our sales strategists. We’ll cover your offer, your lead flow and which service fits. No cost, no obligation. If it’s a fit, you can hand your pipeline to a team that finds, books and closes deals for you.