Outbound Cold Caller - Remote

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.

• 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