Sales Development Representative
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Job Description
Sales Development Representative driving AI-enabled workforce solutions sales for Wing Assistant. Generating qualified sales opportunities through targeted outreach and discovery calls to prospective customers.
Responsibilities:
- Generate and Qualify Pipeline
- 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.
- Research target accounts to understand what they are hiring for, why they may need support, and where Wing could be a strong fit.
- Reach out to prospective customers across email, phone, LinkedIn, and other outbound channels.
- Run focused outbound campaigns around hiring signals, job postings, company growth, and operational pain points.
- Hold early discovery conversations to understand the prospect's hiring needs, pain points, urgency, and openness to remote talent or AI-enabled workforce solutions.
- Communicate what Wing Assistant does and why it matters clearly enough to earn the next meeting.
- 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
- Work hand-in-hand with Account Executives to build and protect a healthy, well-qualified pipeline.
- Hand off opportunities cleanly, with the context AEs need to move deals forward.
- 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.
- Keep activity, notes, and pipeline data accurate and current in our CRM.
- Bring the Market Back In
- Feed what you're hearing from prospects back to the Sales, Marketing, and Product teams.
- Help refine messaging and outreach based on what's actually landing with companies.
- Identify patterns in hiring demand, objections, and industries where Wing is resonating.
- Suggest new outbound angles based on job postings, hiring trends, and prospect conversations.
Requirements:
- 1–4+ years in sales, business development, appointment setting, cold calling, recruiting, staffing, or a comparable outbound role.
- A real interest in B2B sales; bonus points if it's in SaaS, AI, staffing, recruiting, outsourcing, or global workforce operations.
- Proven background in sales prospecting, cold calling, appointment setting, or high-volume outbound outreach.
- Strong written and verbal communication; you can get to the point and make it compelling.
- Comfort reaching out to companies that may not have considered remote assistants, virtual assistants, or offshore talent before.
- Strong research skills and the ability to turn hiring signals into relevant outbound messaging.
- Strong organization and the resilience to keep going when a day doesn't go your way.
- The drive that comes from chasing clear goals, activity metrics, and booked meeting targets.
- The ability to run your own desk while still collaborating well across teams.
- A genuine eagerness to learn the product, the industry, and the sales craft quickly.
Benefits:
- Compensation, Bonus, and Commission
- Performance-based incentives tied to qualified meetings, sales outcomes, and weekly activity targets.
- Earn a bonus for every qualified meeting that shows up.
- Earn an additional bonus when a qualified meeting turns into a closed customer.
- Weekly competitions to keep the team competitive, motivated, and focused on the right activity metrics.
- Designed for SDRs who are driven by targets, enjoy competition, and want direct upside from their effort.
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