Opportunities in Jamaica

Wing Assistant is looking for a highly driven Outbound Cold Caller who thrives on prospecting and opening doors with new potential clients. This role is for someone with a true hunter mindset - someone who is not afraid of rejection, enjoys the challenge of outbound outreach, and is creative in finding ways to engage prospects. You will be responsible for generating qualified meetings and sales opportunities through cold calls, LinkedIn outreach, email campaigns, SMS, and other creative prospecting strategies. If you enjoy the thrill of turning cold prospects into warm opportunities, this role is for you.

Conduct high-volume outbound cold calls to prospective clients

Identify and qualify potential leads and decision-makers

Schedule meetings for the sales team with qualified prospects

Execute multi-channel outreach campaigns including:

Cold calling

LinkedIn prospecting

Email marketing

SMS outreach

Research target accounts and personalize outreach strategies

Consistently meet or exceed outreach and meeting quotas

Maintain accurate records of outreach activities in the CRM

Collaborate with the sales team to improve messaging and conversion

Continuously experiment with creative prospecting techniques

1–3+ years experience in cold calling, SDR, lead generation, or outbound sales

Comfortable making 50–100+ outbound calls daily

Strong communication and persuasion skills

Experience using LinkedIn for prospecting

Familiarity with email outreach tools and CRM systems

Highly resilient and comfortable handling rejection

Strong research skills to identify the right prospects

Self-motivated and results-driven

The ideal candidate:

Has a hunter mentality

Loves outbound sales and prospecting

Is creative with outreach strategies

Is competitive and motivated by hitting targets

Thrives in a fast-paced sales environment