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.
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.
Monitor companies that are posting roles Wing can service.
Position Wing as a faster, more versatile, 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.
Support the Revenue Team
Work closely with the sales team to build and protect a healthy, well-qualified pipeline.
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.
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.
- Comfort reaching out to companies that may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce solutions before.
- A genuine eagerness to learn the product, the market, and the craft of go-to-market execution quickly.

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. 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.
Weekly bonus opportunity for top dial activity.
Weekly bonus opportunity for top meeting production.

📌 Assistant(e) service support ventes - H/F (Montreal)
🏢 Wing Assistant
📍 Montreal