Sales Associate

Wing Assistant is building AI-enabled workforce solutions for growing businesses, helping companies with roles like executive assistance, admin support, customer support, sales support, recruiting support, and operations support.

Location: Canada

Salary: $1,200–$2,500

Responsibilities

• Identify 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 with companies that have a clear hiring need, relevant business use case, or strong fit for Wing.
• Monitor 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.
• Work closely with the sales team to build and protect a healthy, well-qualified pipeline.
• Hand off opportunities cleanly, with the context needed to move conversations 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.
• Feed 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.

Requirements

• 1 to 4+ years in sales, appointment setting, cold calling, recruiting, staffing, lead generation, outbound marketing, growth, or a comparable role.
• A real interest in go-to-market strategy, pipeline generation, and B2B growth.
• Proven background in 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 craft of go-to-market execution quickly.