Sales Development Representative

What You'll Do

Generate and Qualify Pipeline

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Identify companies actively hiring for roles Wing can service, such as Executive Assistants, Admin Assistants, Customer Support, Sales Support, Recruiting Support, Operations Support, and other business support roles.

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Research target accounts to understand what they are hiring for, why they may need support, and where Wing could be a strong fit.

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Reach out to prospective customers across email, phone, LinkedIn, and other outbound channels.

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Run focused outbound campaigns around hiring signals, job postings, company growth, and operational pain points.

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Hold early discovery conversations to understand the prospect's hiring needs, pain points, urgency, and openness to remote talent or AI-enabled workforce solutions.

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Communicate what Wing Assistant does and why it matters clearly enough to earn the next meeting.

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Book qualified appointments for Account Executives with companies that have a clear need, relevant hiring activity, or a strong use case for Wing.

Partner with the Sales Team

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• Work hand-in-hand with Account Executives to build and protect a healthy, well-qualified pipeline.
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• Hand off opportunities cleanly, with the context AEs need to move deals forward.
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• Share key details from discovery calls, including the role the company is hiring for, current hiring process, pain points, timing, budget signals, and decision-makers involved.
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• Keep activity, notes, and pipeline data accurate and current in our CRM.

Bring the Market Back In

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• Feed what you're hearing from prospects back to the Sales, Marketing, and Product teams.
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• Help refine messaging and outreach based on what's actually landing with companies.
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• Identify patterns in hiring demand, objections, and industries where Wing is resonating.
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• Suggest new outbound angles based on job postings, hiring trends, and prospect conversations.

What We're Looking For

Core Requirements

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• 1–4+ years in sales, business development, appointment setting, cold calling, recruiting, staffing, or a comparable outbound role.
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• A real interest in B2B sales; bonus points if it's in SaaS, AI, staffing, recruiting, outsourcing, or global workforce operations.
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• Proven background in sales prospecting, cold calling, appointment setting, or high-volume outbound outreach.
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• Strong written and verbal communication; you can get to the point and make it compelling.
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• Comfort reaching out to companies that may not have considered remote assistants, virtual assistants, or offshore talent before.
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• Strong research skills and the ability to turn hiring signals into relevant outbound messaging.
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• Strong organization and the resilience to keep going when a day doesn't go your way.
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• The drive that comes from chasing clear goals, activity metrics, and booked meeting targets.
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• The ability to run your own desk while still collaborating well across teams.
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• A genuine eagerness to learn the product, the industry, and the sales craft quickly.

Nice to Have

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Exposure to staffing companies, recruiting firms, BPOs, outsourcing companies, virtual assistant companies, digital agent companies, or high-ticket professional services organizations.

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Familiarity with CRM and sales engagement tools such as HubSpot, Salesforce, Outreach, Salesloft, Apollo, Instantly, Clay, Close, or LinkedIn Sales Navigator.

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Familiarity with auto dialers, power dialers, cold calling workflows, and high-volume outbound systems.

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Experience prospecting into founders, executives, operations leaders, HR leaders, recruiting teams, customer support leaders, or sales leaders.

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Awareness of business support workflows such as executive assistance, admin support, sales support, customer support, recruiting coordination, inbox/calendar management, and back-office operations