Remote Telesales Representative / Sales Development Rep (SDR)

Location: All Island Jamaica (Remote Options Available)
Employment Type: Full-Time
Compensation: Performance-Based Commission
Company: Caribbean Closers

About Caribbean Closers

Caribbean Closers is an outsourced sales agency transforming how Caribbean businesses approach sales operations. We partner with wholesale distributors, B2B service providers, and growth-focused companies to build systematic, data-driven sales engines that deliver predictable revenue growth.

The Opportunity

This isn't your typical telesales role. You'll be joining a structured, high-performance sales environment where you'll receive ongoing coaching, proven frameworks, and the tools you need to succeed from day one.

As a Telesales Representative / SDR, you'll focus exclusively on what you do best: finding and qualifying new revenue opportunities in defined product categories and passing sales-ready prospects to our closing team.

You'll operate within:

• Defined product categories (volume wholesale products, high-ticket items like AC systems, water heaters, solar/energy solutions)

• Targeted verticals (property managers, contractors, hospitality, commercial buyers)

• Proven systems (CRM workflows, qualification checklists, conversion-optimized scripts)

What You'll Own

Prospecting & Lead Generation

• Conduct outbound prospecting into assigned verticals using multi-channel approach (phone, WhatsApp, email)

• Follow up on inbound leads for assigned product categories with speed and precision

• Build and maintain target account lists within your territory

Qualification & Discovery

• Qualify prospects using our proven framework

• Conduct discovery calls to understand customer pain points and project requirements

• Document all prospect information accurately in the CRM

Meeting Coordination

• Book qualified meetings and demos for Field Sales team

• Ensure seamless handoff with complete context and next steps

• Maintain communication with prospects through the sales cycle

CRM & Data Excellence

• Maintain 100% CRM accuracy and compliance

• Track all activities, conversations, and outcomes daily

• Provide weekly reporting on pipeline health and qualification metrics

What Success Looks Like (Your KPIs)

Activity Metrics:

• Contact rate: First touchpoint within 2 hours of lead assignment

• Daily activity: Minimum call/contact volume targets

• CRM compliance: 100% data accuracy

Performance Metrics:

• Qualified meetings booked per week

• Opportunity acceptance rate by Field Sales (quality over quantity)

• Conversion rate from qualified opportunity → closed deal (lagging indicator)

You'll know exactly where you stand through weekly scorecards and regular coaching sessions with sales leadership.

Who You Are

Required Experience & Skills

• 1-3 years in telesales, inside sales, or customer-facing phone-based role

• Proven track record of meeting or exceeding activity and conversion targets

• Experience using CRM systems (Salesforce, HubSpot, Zoho, or similar)

• Strong phone presence with excellent verbal communication skills

• Comfortable with consultative selling and asking discovery questions

Preferred Qualifications

• Experience in B2B sales, wholesale, distribution, or construction/contractor sales

• Previous experience in structured sales organizations with defined processes

• Previous remote work experience or successful self-employment

Personal Attributes

• Self-motivated: You don't need to be micromanaged to stay productive

• Coachable: You actively seek feedback and implement it quickly

• Organized: You manage your pipeline, follow-up tasks, and time effectively

• Resilient: You handle rejection professionally and bounce back quickly

• Curious: You ask great questions and genuinely want to understand customer needs

• Team player: You celebrate when Field Sales closes deals you qualified

What We Offer

Compensation & Incentives

• Performance-based commission structure

• Monthly bonuses for hitting meeting-booking and conversion targets

• Quarterly performance reviews with raise opportunities

Professional Development

• Ongoing sales training

• Weekly coaching sessions with experienced sales leadership

• Access to proven scripts, frameworks, and playbooks from day one

• Clear career progression path to Account Executive or Sales Team Lead roles

Tools & Support

• Modern CRM system with automation workflows

• Phone credit and communication tools provided

• Access to product knowledge resources and training materials

Work Environment

• Flexible hybrid/remote work options available

• Collaborative team culture focused on continuous improvement

• Regular team huddles and performance celebrations

• Transparent reporting - you'll always know how you're performing

How to Apply

If you're ready to join a structured, high-performance sales environment where your efforts are supported by proven systems and experienced leadership, we want to hear from you.

Click here to send your application

Selection Process

1. Application Review (48-72 hours)

2. Phone Screen (15-20 minutes with Recruiting Team)

3. Skills Assessment (Role-play discovery call scenario)

4. Final Interview (Meeting with Sales Leadership)

5. Offer & Onboarding

We move quickly for the right candidates. Top performers can expect to go from application to offer within 2 weeks.

Questions?

Email us at [email protected] or visit www.caribbeanclosers.com to learn more about our company and approach.

Caribbean Closers is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all team members.