Outbound Cold Caller

Wing Assistant is seeking a Head of Training & Development to dismantle our current training model and build a world-class, multi-week Performance Academy from the ground up. This is a foundational, hands-on leadership position, you'll personally design curriculum, lead live training sessions, and establish the systems that define how Wing develops talent at scale before transitioning into a strategic leadership role as the department matures.

We onboard 200+ VAs monthly and are transforming from basic orientation into a comprehensive training operation. If you've built training programs from scratch at Virtual Assistant Companies, BPOs or similar, this is your opportunity to do it again with full ownership and executive backing.

Responsibilities

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

Requirements

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

Ideal Candidate

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