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