Playbook 2026 Edition 12 min read

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The Caribbean Hiring Playbook

Nobody has published the Caribbean-specific version of a hiring guide. So this is it. Written for US founders, ops leaders, and hiring managers who want strong remote talent without gambling on a hire they can't support.

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Accuracy note: Rates change. Figures were checked against published payroll references in 2026 and are for planning only. Confirm with local counsel or a payroll provider. This is general information, not legal or tax advice.

01 โ€” The Case

Why look here

Three practical reasons US teams build across the Caribbean and Latin America.

Time zones

Jamaica, Colombia, and Peru are on UTC-5 all year with no daylight saving. Costa Rica is UTC-6 all year. Real overlap, no shifting clocks.

Cost

Entry level roles from about $7/hr versus roughly $25/hr typical in the US. Over 2,080 hours that's about $37,440 per hire (illustration only).

Retention

A fair salary beats the lowest price. Cheap hires who leave cost you re-hiring, retraining, and customer trust.

02 โ€” Pick a Model

Choose your hiring model

The model you pick decides who owns payroll, compliance, and contracts. Get this right before you source.

1

Placement fee

Agency sources and vets, you hire and manage directly. Best if you have local payroll support.

You own payroll, compliance, and contracts.

2

Employer of Record (EOR)

The EOR employs them locally and handles payroll, taxes, and HR. Best if you have no local entity.

Ongoing monthly fee.

3

Contractor

Person invoices you. Best for short, scoped projects.

Risk: misclassification if they work like an employee.

03 โ€” Stay Compliant

Compliance and payroll

Ask five questions in every country: contract type, payroll taxes, mandatory pay, filing deadlines, data privacy.

The five questions

  • 1 Contract type
  • 2 Payroll taxes
  • 3 Mandatory pay
  • 4 Filing deadlines
  • 5 Data privacy

Examples to verify: Mexico's aguinaldo, Brazil's 13th salary, Colombia's service and severance payments.

๐Ÿ‡ฏ๐Ÿ‡ฒ

Jamaica example

  • NIS 3% employer ยท 3% employee
    J$5,000,000 annual ceiling
  • NHT 3% employer ยท 2% employee
  • Education Tax 3.5% employer ยท 2.25% employee
  • HEART/NSTA 3% employer only
  • PAYE 0% under J$1,902,360
    25% up to J$6,000,000
    30% above
    Apr 2026 โ€“ Mar 2027
  • Filing By the 14th of the
    following month

Employer costs add about 12.5%

So J$100,000 gross costs about J$112,500.

04 โ€” Do the Math

Budget the real cost

The hourly rate is not the cost. Build your budget from every line below.

Base salary
Statutory employer costs
Mandatory pay
Service fee
Tools and equipment
30 days of ramp time

Payment method

Ask about bank transfer, Payoneer, or PayPal.

Confirm the pay date

Agree it before day one. No surprises either side.

Review pay

Revisit at 6 to 12 months to keep good people.

05 โ€” Make It Work

Integrate across cultures

Great hires still fail without good integration. Three areas to get right.

Communication

  • State needs and deadlines plainly.
  • Explain US idioms and customer context.
  • Invite questions publicly.
  • Give written feedback with examples.

Rhythm

  • Agree overlap hours.
  • Share holidays in advance.
  • Hold weekly one on ones for three months.
  • Write 30/60/90 day goals.

Belonging

  • Assign a buddy.
  • Celebrate wins.
  • Pronounce names correctly.

06 โ€” Get Them Started

Hire and onboard

A realistic timeline from consultation to a fully onboarded hire.

Day 1

Consultation

Scope the role, model, and budget.

Days 2โ€“5

Sourcing and vetting

We find and screen the shortlist.

Days 6โ€“7

Interviews

You meet vetted candidates.

Week 2 onward

Offer and onboarding

Offer, paperwork, and day one.

First 30 days

Week 1

Tools, product, introductions, shadowing.

Week 2

Guided practice with review.

Week 3

Speed, judgment, first feedback.

Week 4

Full ownership and a 60 day plan.

Act within 48 hours if

They're struggling with basics by day 10, go quiet, or miss check-ins.

07 โ€” Proof

Placement snapshots

Two examples of what this looks like in practice.

Director of Engineering

A DevOps role sat open for months. Filled in under two weeks, and a second hire followed.

VP of People and Operations

Needed support coverage. Three strong candidates sent, the hire performed well, and the next hire is planned.

Jamaica-founded ยท Globally minded

About Maverick Desks

Jamaica-founded talent firm connecting US companies with vetted professionals across the Caribbean and Latin America. One-time placement fee or managed EOR, with a 30 day replacement guarantee.

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maverickdesks.co