GTM Sales

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Wing Assistant is building AI-enabled workforce solutions and seeks a Go-to-Market Associate in Calgary to front the revenue engine by identifying companies with active hiring needs, running outbound campaigns, and booking qualified meetings for the sales team. This high-energy, ownership-driven role favors 1 to 4+ years in sales or outbound work, a proven ability to prospect and set appointments, and comfort turning hiring signals into outreach. You’ll research target accounts, reach out across email, phone, LinkedIn and other channels, and keep CRM data clean while collaborating with revenue teams. To apply, tailor your resume to GTM results, quantify your wins, cite CRM/tools familiarity, and include a brief case for converting signals into meetings.

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.

What You'll Do

Generate Qualified Opportunities

• 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.

Turn Hiring Intent Into Conversations

• 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.

Support the Revenue Team

• 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.

Bring the Market Back In

• 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.

 

What We're Looking For

Core 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 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, 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.