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 transparent 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 solid 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

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

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

This means you are rewarded not just for booking activity, but for creating real opportunities that move through the revenue process.

Weekly Competitions

Weekly bonus opportunity for top dial activity

Weekly bonus opportunity for top meeting production

These incentives are designed for people who are driven by targets, enjoy competition, and want direct upside from their effort.

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📌 GTM Associate (Manitoba)
🏢 Wing Assistant
📍 Manitoba