Sales Development Representative

About the Company
Wing Assistant is building the next generation of AI-enabled workforce solutions for growing businesses. We help companies get high-quality support across roles like executive assistance, admin support, customer support, sales support, recruiting support, operations support, and other business functions.

About the Role

Our growth depends on a steady flow of qualified sales opportunities, and we are hiring a Sales Development Representative to help create them. This person will be on the front lines of our go-to-market motion: identifying companies that are actively hiring for roles Wing can support, reaching out with a compelling alternative to traditional hiring, and booking qualified meetings for our Account Executives. This is a high-energy, high-ownership seat for someone early in their sales career who wants to learn fast, build real outbound skills, and grow into bigger sales or go-to-market roles over time. It is a great fit for someone who is competitive, well-organized, motivated by clear targets, and genuinely curious about how AI, remote talent, and global workforce solutions are changing the way companies build teams.

Responsibilities

Generate and Qualify PipelineIdentify companies actively hiring for roles Wing can support, such as Executive Assistants, Admin Assistants, Customer Support, Sales Support, Recruiting Support, Operations Support, and other business support roles.Use job postings, hiring signals, company growth signals, and account research to find strong-fit prospects.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 active hiring needs, operational pain points, and alternative workforce solutions.Hold early discovery conversations to understand a 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 hiring need, relevant business use case, or strong fit for Wing.
Turn Hiring Intent Into Sales OpportunitiesMonitor companies that are posting roles Wing can service.Understand what the company is likely trying to solve by hiring that role.Position Wing as a faster, more flexible, and more scalable alternative to traditional hiring.Educate prospects who may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce support before.Create curiosity with founders, executives, operators, HR leaders, recruiting teams, and department heads.
Partner with the Sales TeamWork 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, their 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 InFeed what you are hearing from prospects back to the Sales, Marketing, and Product teams.Help refine messaging and outreach based on what is actually landing with companies.Identify patterns in hiring demand, objections, industries, and roles where Wing is resonating.Suggest new outbound angles based on job postings, hiring trends, and prospect conversations.

Qualifications

1 to 4+ years in sales, business development, appointment setting, cold calling, recruiting, staffing, or a comparable outbound role.A real interest in B2B sales, go-to-market strategy, and pipeline generation.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, offshore talent, or AI-enabled workforce solutions 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 does not 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 market, and the sales craft quickly.

Required Skills

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

Pay range and compensation package

In addition to base compensation, this role includes performance-based incentives tied to qualified meetings, sales outcomes, and weekly activity targets.
Appointment and Deal BonusesEarn a bonus for every qualified meeting that shows up.Earn an additional bonus when a qualified meeting turns into a closed customer. This means you are rewarded not just for booking activity, but for creating real opportunities that move through the sales process.