GTM Sales

Wing Assistant • Calgary, AB

6d • $1,200 - $2,500

About The Position

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.
Our growth depends on a steady flow of qualified opportunities, and we are hiring a Go-to-Market Associate to help create them. This person will sit at the front line of our revenue motion: identifying companies with active hiring needs, reaching out with a compelling alternative to traditional hiring, and booking qualified meetings for our sales team.
This is a high-energy, high-ownership role for someone early in their career who wants to learn fast, build real outbound skills, and grow into bigger roles across sales, growth, revenue, or go-to-market strategy 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.

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.

Nice To Haves

• 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.

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.

Benefits

• In addition to base compensation, this role includes performance-based incentives tied to qualified meetings, sales outcomes, and weekly activity targets.
• Appointment and Deal Bonuses
• 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
• Weekly bonus opportunity for top dial activity.
• Weekly bonus opportunity for top meeting production.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed