Sales Development Representative

What You'll Do

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.

What We're Looking For

Core 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.

Nice to Have

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

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

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

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

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