Sales Hiring: What Caribbean Companies Get Wrong & How to Get It Right

For years, companies across Guyana, Jamaica, Trinidad & Tobago, and the wider Caribbean have struggled with hiring and retaining top sales talent. The common complaint?

"Good salespeople are hard to find."

But is the problem really the talent pool?

From analyzing 84 sales job descriptions across multiple industries, we’ve found that:

• Many job postings are misaligned with real sales objectives.
• Companies fail to differentiate between hunters (new business sales reps) and farmers (account management).
• Compensation structures don’t always drive performance.
• HR and Sales Managers often don’t collaborate effectively on hiring.

This isn’t a new issue. We’ve been tracking sales hiring challenges since 2020, and our early research pointed to the same misalignment issues. (📺 See our 2020 research video below.

Originally published: May 2020

The Result?

• Salespeople are hired for the wrong reasons.
• Performance expectations don’t match job realities.
• Companies waste time and money on bad hires.

Let’s break down what’s happening, what the data says, and how companies can fix it.

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Overview of the research:

• Data Source: 2 Websites (JobsTT, CaribbeanJobs)
• Period: October 1st - December 2024
• Geographic Focus: Guyana, Jamaica, Trinidad & Tobago
• Total Sales Job Descriptions Analyzed: 85 (so far and growing)

Why does this matter?

• Sales hiring misalignments affect revenue, employee retention, and productivity.
• Sales job descriptions are often unclear, outdated, or unrealistic.
• New roles emerging in 2024 (CRO, Sales Operations, Sales Enablement, Social Selling).

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Section 1: What the Data Says – Sales Hiring Trends in the Caribbean

We analyzed 84 job descriptions from FMCG, Insurance, Retail, B2B, Medical Sales, and Industrial Sales. Here’s how sales hiring breaks down:

Industry Breakdown – Where Sales Jobs Are Most in Demand

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Key Takeaway:

• Retail & FMCG reps spend too much time on admin.
• Medical sales lacks modern tools (virtual sales, AI-driven prospecting).
• The Insurance sales industry still relies too much on traditional lead-generation strategies.

✅ Best Practice for Employers:
If you’re hiring for Retail, FMCG, or Medical Sales, ensure your job descriptions reflect the specific sales motions needed.

• FMCG reps should focus on product placement, distributor relations & merchandising.
• Medical sales reps should be trained on product knowledge, but also AI-powered sales tools like digital demos & webinars.
• Insurance sales should prioritize digital prospecting & LinkedIn networking, not just cold calling.

✅ Action Step for Job Seekers:
Before applying for a sales role, ask yourself:

• Am I a hunter (new business) or a farmer (relationship builder)?
• Do I have the right industry-specific skills?
• Does this company provide sales enablement tools, or are they using outdated sales methods?

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Section 2: What’s Wrong with Sales Hiring? (Gaps & Challenges)

A mistake many companies make is not defining whether they need a Hunter or a Farmer. This leads to misaligned compensation, poor performance, and high turnover.

Beverley Thompson (Sales & Business Development Trainer, Jamaica) explained this well in our discussion on base salary vs. commission:

"When companies offer high base salaries, many salespeople get comfortable and stop pushing for performance. On the other hand, a commission-only model can discourage effort if the earning potential isn’t clear."

Best Practice for Employers

Hiring the wrong type of salesperson leads to frustration, high turnover, and underperformance.

• Hunters thrive in new business development and should be incentivized with aggressive commission structures.
• Farmers excel in relationship-driven roles and should have higher base salaries with retention incentives.
• Companies should clearly state in job descriptions whether the role requires a Hunter or a Farmer.

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Section 3A: Salary & Commission Trends – What Sales Roles Pay in the Caribbean

Compensation is one of the most misunderstood aspects of sales hiring. Many companies fail to structure salaries properly, leading to low motivation, poor performance, and frequent turnover.

📊 Salary Breakdown by Role

Key Takeaway:

• Medical & Key Account Sales offer the highest base salaries.
• Insurance & Real Estate Sales rely heavily on performance-based commissions.

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Section 3B: Qualification Trends – What Employers Look For vs. What Sales Actually Needs

Many job descriptions still require outdated qualifications, such as degrees that have little impact on sales performance. Instead, companies should focus on practical skills & certifications.

📊 Key Findings

Key Takeaway:

• Degree requirements could be relaxed in favour of skill-based hiring.
• There are more updated courses that support the skills needed in 2025. (See later section)
• CRM training should be provided rather than assumed.
• Quota expectations need to be clearly defined upfront.

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Section 4: HR’s Role in Sales Hiring & Sales Performance Management

Why HR Needs to Take an Active Role in Sales Hiring

• HR shouldn’t just post job descriptions & screen resumes—they need to ensure job descriptions align with real sales objectives.
• Too often, HR relies solely on the sales manager’s input, but sales leaders may not always articulate hiring needs properly.
• HR must act as a strategic partner & hiring consultant—ensuring that each role has the right competencies, performance structure, and compensation alignment.

HR’s Key Responsibilities in Sales Hiring

• Consulting Sales Leadership on Role Structure – Helping define Hunters vs. Farmers clearly before posting a job.
• Ensuring Hiring Profiles Align with Business Goals – If the goal is new business growth, the role should focus on outbound, prospecting-heavy reps, not customer service-heavy reps.
• Performance Management & Sales Enablement Support – HR needs to be proactive in coaching, training & performance tracking, ensuring salespeople have the right tools & frameworks to succeed.

The Cost of Hiring the Wrong Salespeople (HR’s Business Case for Doing This Right)

• Hiring misaligned sales talent = Lost revenue, wasted time, and increased turnover costs.
• Bad job descriptions = bad hires = underperformance = expensive exits.
• It’s harder to exit a bad hire than to hire correctly the first time—HR must push for precision in job postings.

✅ Where HR Can Improve Sales Hiring

• Work with Sales Enablement & Sales Ops teams to create onboarding & training roadmaps.
• Ensure clear commission structures to avoid demotivation & high attrition.
• Regularly update sales job descriptions to reflect modern selling techniques (social selling, AI prospecting, CRM automation, etc.).

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Section 5: What Sales Hiring Needs in 2025 & Beyond

Most job descriptions still focus on traditional sales skills. But in 2025 and moving forward, sales teams will need the following.

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Recommended Sales Courses & Certifications for 2025

In 2025, companies should start prioritizing sales certifications like these:

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Final Thoughts: The Future of Sales Hiring in the Caribbean

As we move into 2025 and beyond, companies that fail to adapt their hiring strategies will continue to struggle with sales performance and retention.

What Needs to Change?

• 1️⃣ Sales hiring should be skills-based, not degree-based.
• 2️⃣ Sales roles should be clearly defined (Hunters vs. Farmers).
• 3️⃣ HR must collaborate closely with Sales to ensure role alignment.
• 4️⃣ Companies must invest in training for modern sales techniques (AI, automation, social selling).

The sales landscape is evolving faster than ever. Organisations that refuse to update their hiring strategies will continue to suffer from high turnover, misaligned talent, and lost revenue.

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Action Plan for Employers & Job Seekers

✅ For Employers:

• Rewrite your job descriptions to reflect the actual role & skills needed.
• Align compensation structures with performance expectations.
• Invest in onboarding & ongoing sales enablement—don’t just expect talent to "figure it out."
• Encourage certifications & training instead of just requiring degrees.

✅ For Job Seekers:

• Focus on upskilling—learn modern sales techniques like AI-driven selling & social selling.
• Earn industry-relevant certifications to stand out in competitive job markets.
• Clarify expectations in job interviews—understand commission structures, quotas, and job responsibilities before accepting offers.

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